Title: Book The Best Hotels in Shelter Island, NY for 2026 from CA $103 - Fully Refundable Options - Expedia.ca

[Shelter Island Travel Guide](https://expedia.ca/Shelter-Island.dx157359)[Vacation Rentals in Shelter Island](https://expedia.ca/Shelter-Island-Vacation-Rentals.d157359.Travel-Guide-VacationRentals)[Flights to Shelter Island](https://expedia.ca/Cheap-Flights-To-Shelter-Island.d157359.Travel-Guide-Flights)[Things to do in Shelter Island](https://expedia.ca/Things-To-Do-In-Shelter-Island.d157359.Travel-Guide-Activities)[Shelter Island Car Rentals](https://expedia.ca/Car-Rentals-In-Shelter-Island.d157359.Car-Rental-Guide)[Shelter Island Vacation Packages](https://expedia.ca/Shelter-Island.d157359.Destination-Travel-Guides)

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## Go beyond your typical stay in Shelter Island

Pet friendly

[](https://www.expedia.ca/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America&regionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-03-29&d1=2026-03-29&endDate=2026-03-31&d2=2026-03-31&amenities=PETS)

Pool

[](https://www.expedia.ca/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America&regionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-03-29&d1=2026-03-29&endDate=2026-03-31&d2=2026-03-31&amenities=POOL)

Spa

[](https://www.expedia.ca/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America&regionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-03-29&d1=2026-03-29&endDate=2026-03-31&d2=2026-03-31&amenities=SPA_ON_SITE)

Hot tub

[](https://www.expedia.ca/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America&regionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-03-29&d1=2026-03-29&endDate=2026-03-31&d2=2026-03-31&amenities=HOT_TUB)

Family friendly

[](https://www.expedia.ca/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America&regionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-03-29&d1=2026-03-29&endDate=2026-03-31&d2=2026-03-31&travelerType=family_friendly)

Cottage

[](https://www.expedia.ca/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America&regionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-03-29&d1=2026-03-29&endDate=2026-03-31&d2=2026-03-31&lodging=COTTAGE)

Apart­ment

[](https://www.expedia.ca/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America&regionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-03-29&d1=2026-03-29&endDate=2026-03-31&d2=2026-03-31&lodging=APARTMENT)

## Check prices for these dates

Tonight

[Mar 15 - Mar 16](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2026-03-15&endDate=2026-03-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Mar 16 - Mar 17](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2026-03-16&endDate=2026-03-17&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2026-03-20&endDate=2026-03-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2026-03-27&endDate=2026-03-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Shelter Island hotels

![Resort view](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/7aeccb7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Yoga](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/a7c5a78c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room, 1 King Bed](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/ac1b5094.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lunch, dinner, brunch served; American cuisine, beach views ](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/55b708b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sound View Greenport

[](https://www.expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information)

Greenport

8.4/10

Very good

(620 reviews)

"The hotel was exceptional! We love staying at soundview during the winter months! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Christina

CA $191

CA $257 total

includes taxes & fees

Mar 23 - Mar 24

[](https://www.expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information)

![Lobby lounge](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/2c9cc7e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby lounge](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/717b3774.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from room](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/7ebc6d88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool, open 8:00 AM to 7:00 PM, sun loungers](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/1345db22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Harbor Front Inn

[](https://www.expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information)

Greenport

8.8/10

Excellent

(573 reviews)

"Room was beautiful and everyone who worked there was very nice. We’d love to go back! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Mary

CA $184

CA $249 total

includes taxes & fees

Mar 16 - Mar 17

[](https://www.expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information)

![Beach bar](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/52eefc00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Waterfront Beach Shack Studio](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/1c4953c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Waterfront Beach Shack Studio](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/244f3d92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from room](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/2d824970.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Silver Sands Motel & Beach Bungalows

[](https://www.expedia.ca/Greenport-Hotels-Silver-Sands.h91068954.Hotel-Information)

Greenport

9.8/10

Exceptional

(148 reviews)

"Everything was excellent, best hotel on the north fork. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Dan

CA $261

CA $299 total

includes taxes & fees

Mar 19 - Mar 20

[](https://www.expedia.ca/Greenport-Hotels-Silver-Sands.h91068954.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/7000000/6480000/6473500/6473437/daf99b53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, individually furnished, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/7000000/6480000/6473500/6473437/7a760b80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast, lunch, dinner served; local cuisine, ocean views ](https://images.trvl-media.com/lodging/7000000/6480000/6473500/6473437/w2880h1617x0y0-215d1f51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private beach, sun loungers, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/7000000/6480000/6473500/6473437/ad990fb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Pridwin Hotel

[](https://www.expedia.ca/Shelter-Island-Heights-Hotels-The-Pridwin-Hotel.h6473437.Hotel-Information)

Shelter Island Heights

9.6/10

Exceptional

(84 reviews)

"Overall the places is nice, clean and great views"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Dianne

[](https://www.expedia.ca/Shelter-Island-Heights-Hotels-The-Pridwin-Hotel.h6473437.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/5a27472c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/7f5c2322.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace King](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/efe41897.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace King | Living area](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/582203a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Shoals Suites and Slips

[](https://www.expedia.ca/Southold-Hotels-The-Shoals-Suites-And-Slips.h76716269.Hotel-Information)

Southold

9.4/10

Exceptional

(245 reviews)

"Great stay, will definitely go again"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

ANTONIO J

CA $209

CA $239 total

includes taxes & fees

Mar 24 - Mar 25

[](https://www.expedia.ca/Southold-Hotels-The-Shoals-Suites-And-Slips.h76716269.Hotel-Information)

![Beach nearby](https://images.trvl-media.com/lodging/19000000/18640000/18632700/18632615/affe9b7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/19000000/18640000/18632700/18632615/06513245.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room, 1 King Bed](https://images.trvl-media.com/lodging/19000000/18640000/18632700/18632615/556419e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 King Bed, Kitchenette (Living Room) | Living room](https://images.trvl-media.com/lodging/19000000/18640000/18632700/18632615/9e5e2d70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### West Neck Guesthouse

[](https://www.expedia.ca/Shelter-Island-Heights-Hotels-West-Neck-Guesthouse.h18632615.Hotel-Information)

Shelter Island Heights

8.0/10

Very good

(37 reviews)

"Great property! Close to beach and super clean. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Leslie

[](https://www.expedia.ca/Shelter-Island-Heights-Hotels-West-Neck-Guesthouse.h18632615.Hotel-Information)

![Sundeck](https://images.trvl-media.com/lodging/36000000/35230000/35229400/35229370/dc6eb455.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/36000000/35230000/35229400/35229370/f0f56ac7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast served](https://images.trvl-media.com/lodging/36000000/35230000/35229400/35229370/29d9fdab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/36000000/35230000/35229400/35229370/3451f87b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Menhaden

[](https://www.expedia.ca/Greenport-Hotels-The-Menhaden.h35229370.Hotel-Information)

Greenport

9.6/10

Exceptional

(177 reviews)

"Wonderful stay in a quaint hotel..The small town was amazing and had such cozy welcoming atmosphere! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Cory

CA $357

CA $463 total

includes taxes & fees

Mar 16 - Mar 17

[](https://www.expedia.ca/Greenport-Hotels-The-Menhaden.h35229370.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/68000000/67570000/67569900/67569836/e8baba10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from room](https://images.trvl-media.com/lodging/68000000/67570000/67569900/67569836/620f075e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Frette Italian sheets, premium bedding, blackout drapes](https://images.trvl-media.com/lodging/68000000/67570000/67569900/67569836/587cd5ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Frette Italian sheets, premium bedding, blackout drapes](https://images.trvl-media.com/lodging/68000000/67570000/67569900/67569836/e70a9337.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Chequit

[](https://www.expedia.ca/Shelter-Island-Heights-Hotels-The-Chequit.h67569836.Hotel-Information)

The Heights

9.0/10

Wonderful

(37 reviews)

"A cozy room with great pillows and quiet. Perfect little place. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Neal

[](https://www.expedia.ca/Shelter-Island-Heights-Hotels-The-Chequit.h67569836.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/23000000/22810000/22804900/22804880/767254d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/23000000/22810000/22804900/22804880/addc6353.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/23000000/22810000/22804900/22804880/ff45254e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![On the beach](https://images.trvl-media.com/lodging/23000000/22810000/22804900/22804880/6e8b34ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Harbor Knoll Bed & Breakfast

[](https://www.expedia.ca/Greenport-Hotels-Harbor-Knoll-Bed-Breakfast.h22804880.Hotel-Information)

Pipes Cove

9.2/10

Wonderful

(12 reviews)

"It was very pleasant. We would stay again someday. Very convenient to restaurants in town and ferry. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Andrea

[](https://www.expedia.ca/Greenport-Hotels-Harbor-Knoll-Bed-Breakfast.h22804880.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/2000000/1780000/1771100/1771009/382fd5ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/2000000/1780000/1771100/1771009/8d30d692.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/2000000/1780000/1771100/1771009/0ec625aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1780000/1771100/1771009/354d428b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stirling House Bed & Breakfast

[](https://www.expedia.ca/Greenport-Hotels-Stirling-House-Bed-Breakfast.h1771009.Hotel-Information)

Greenport

9.8/10

Exceptional

(24 reviews)

"This was a great place to stay with old word charm. If you are looking for a quiet getaway with a beautiful view of the ocean this is it. The breakfast that we had were much better that what you could get in town. My wife and I can't wait to go back."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

steve

[](https://www.expedia.ca/Greenport-Hotels-Stirling-House-Bed-Breakfast.h1771009.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/12000000/11960000/11951200/11951124/81e91eb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/12000000/11960000/11951200/11951124/6603a689.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/12000000/11960000/11951200/11951124/65a6ec82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/12000000/11960000/11951200/11951124/9091cefd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### American Beech Hotel

[](https://www.expedia.ca/Greenport-Hotels-American-Beech-Hotel.h11951124.Hotel-Information)

Greenport

8.8/10

Excellent

(198 reviews)

"Very nice and very clean."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Daniel

CA $295

CA $392 total

includes taxes & fees

Mar 16 - Mar 17

[](https://www.expedia.ca/Greenport-Hotels-American-Beech-Hotel.h11951124.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/f2951978.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/942c49f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private Suite, 1 King Bed, Non Smoking (Private Suite - Adults Only)](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/d6ac52f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden Suite, Wheelchair Accessible, Ground Floor, 2 Queen Beds, Non-Smoking](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/8dd4e80f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Zey Hotel

[](https://www.expedia.ca/Greenport-Hotels-The-Gallery-Hotel.h15622089.Hotel-Information)

Greenport

9.2/10

Wonderful

(299 reviews)

"Quiet yet situated right in the heart of Greenport."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Andrew

CA $444

CA $508 total

includes taxes & fees

Mar 16 - Mar 17

[](https://www.expedia.ca/Greenport-Hotels-The-Gallery-Hotel.h15622089.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/11000000/10330000/10328200/10328173/c201860e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, Frette Italian sheets, premium bedding, pillowtop beds](https://images.trvl-media.com/lodging/11000000/10330000/10328200/10328173/45f7f9be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception hall](https://images.trvl-media.com/lodging/11000000/10330000/10328200/10328173/efd040c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/11000000/10330000/10328200/10328173/e2e6a02e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Arbor View House B&B

[](https://www.expedia.ca/East-Marion-Hotels-Arbor-View-House-Bed-And-Breakfast.h10328173.Hotel-Information)

East Marion

9.2/10

Wonderful

(15 reviews)

"Two mid age couples just had a good and relaxing time with great hospitality. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Michail

[](https://www.expedia.ca/East-Marion-Hotels-Arbor-View-House-Bed-And-Breakfast.h10328173.Hotel-Information)

![Front of property - evening/night](https://images.trvl-media.com/lodging/15000000/15000000/14997600/14997595/b156868f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/15000000/15000000/14997600/14997595/9f8ccc73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/15000000/15000000/14997600/14997595/c4a7db4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/15000000/15000000/14997600/14997595/89ad2223.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Shelter Island House

[](https://www.expedia.ca/Shelter-Island-Heights-Hotels-Shelter-Island-House.h14997595.Hotel-Information)

Shelter Island Heights

8.4/10

Very good

(57 reviews)

"We liked the areas for sitting outside, to sit with a coffee, talk and relax. It was convenient to have a fridge. A very different accommodation but typical for the island. We enjoyed our stay!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

James

[](https://www.expedia.ca/Shelter-Island-Heights-Hotels-Shelter-Island-House.h14997595.Hotel-Information)

![Lobby lounge](https://images.trvl-media.com/lodging/92000000/91480000/91472700/91472602/e7ab535b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private beach, sun loungers, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/92000000/91480000/91472700/91472602/a6448db7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool, open 8:00 AM to 7:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/92000000/91480000/91472700/91472602/48ec4beb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private beach, sun loungers, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/92000000/91480000/91472700/91472602/d6c9f61c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel Moraine

[](https://www.expedia.ca/Greenport-Hotels-Hotel-Moraine.h91472602.Hotel-Information)

Greenport

9.8/10

Exceptional

(22 reviews)

"Our 3rd stay - we love the beauty of the property and the luxurious serenity of this boutique hotel. Great views of the water; fantastic large pool and lounging areas."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Amy

[](https://www.expedia.ca/Greenport-Hotels-Hotel-Moraine.h91472602.Hotel-Information)

![Condo | Terrace/patio](https://images.trvl-media.com/lodging/11000000/10450000/10449100/10449005/f965a09e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby](https://images.trvl-media.com/lodging/11000000/10450000/10449100/10449005/c4e4571c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Condo](https://images.trvl-media.com/lodging/11000000/10450000/10449100/10449005/fa408cbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool, open 9:00 AM to 7:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/11000000/10450000/10449100/10449005/0090e01f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cliffside Resort Condominiums

[](https://www.expedia.ca/Greenport-Hotels-Cliffside-Resort-Condominiums.h10449005.Hotel-Information)

Greenport

9.0/10

Wonderful

(249 reviews)

"Great stay - beautiful place"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Rebecca

CA $238

CA $331 total

includes taxes & fees

Mar 16 - Mar 17

[](https://www.expedia.ca/Greenport-Hotels-Cliffside-Resort-Condominiums.h10449005.Hotel-Information)

![Hypo-allergenic bedding, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/106000000/105620000/105612600/105612509/4f9ecb0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor spa tub](https://images.trvl-media.com/lodging/106000000/105620000/105612600/105612509/f2df1f38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105620000/105612600/105612509/7a84d66f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from room](https://images.trvl-media.com/lodging/106000000/105620000/105612600/105612509/5c54f260.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Montauk Blue Hotel

[](https://www.expedia.ca/Montauk-Hotels-Montauk-Blue-Hotel.h105612509.Hotel-Information)

Downtown Montauk

9.2/10

Wonderful

(188 reviews)

"Great view of sunrise and sunset "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Christopher

[](https://www.expedia.ca/Montauk-Hotels-Montauk-Blue-Hotel.h105612509.Hotel-Information)

![Building design](https://images.trvl-media.com/lodging/27000000/26500000/26497900/26497858/1c345cd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/27000000/26500000/26497900/26497858/14a9b9bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby lounge](https://images.trvl-media.com/lodging/27000000/26500000/26497900/26497858/6037fc82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/27000000/26500000/26497900/26497858/f95ca887.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sag Harbor Inn

[](https://www.expedia.ca/Sag-Harbor-Hotels-Sag-Harbor-Inn.h26497858.Hotel-Information)

Sag Harbor

9.4/10

Exceptional

(584 reviews)

"Lovely hotel, very clean and friendly! Definitely going back!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Hollie

CA $281

CA $321 total

includes taxes & fees

Mar 16 - Mar 17

[](https://www.expedia.ca/Sag-Harbor-Hotels-Sag-Harbor-Inn.h26497858.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/935ed559.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/c3d8e2ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/3c3df51f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/c7d19019.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Greenporter Hotel

[](https://www.expedia.ca/Greenport-Hotels-Greenporter-Hotel.h90308554.Hotel-Information)

Greenport

9.2/10

Wonderful

(284 reviews)

"Great location, great hotel, great staff! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jenny

[](https://www.expedia.ca/Greenport-Hotels-Greenporter-Hotel.h90308554.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/28000000/27200000/27194600/27194600/bca4c06d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bay Twin Room](https://images.trvl-media.com/lodging/28000000/27200000/27194600/27194600/bd4c3d0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby](https://images.trvl-media.com/lodging/28000000/27200000/27194600/27194600/292cb4ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/28000000/27200000/27194600/27194600/dc079db7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### A Room At The Beach

[](https://www.expedia.ca/Bridgehampton-Hotels-A-Room-At-The-Beach.h27194600.Hotel-Information)

Bridgehampton

9.2/10

Wonderful

(92 reviews)

"Adorable boutique hotel!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Julianne

CA $451

CA $516 total

includes taxes & fees

Apr 1 - Apr 2

[](https://www.expedia.ca/Bridgehampton-Hotels-A-Room-At-The-Beach.h27194600.Hotel-Information)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-03-29&endDate=2026-03-30&regionId=157359&adults=2&sort=RECOMMENDED&openPlayBack=true)

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## 

The Annual Vacation Sale 

Members save up to 40% on hotels and homes. Plan this year’s big trip and save. 

[Book now](https://expedia.ca/deals?rfrr=HTG_SPRING_PROMO_157359)

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Save an average of 15% on thousands of hotels when you're signed in

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## Where to stay in Shelter Island

Find the best Shelter Island areas and neighborhoods for the activities you enjoy most. [Learn more about Shelter Island](https://www.expedia.ca/Shelter-Island.dx157359)

- Silver Beach
- Menantic Creek
- Coecles Harbor
- Hay Beach
- Shorewood

![Center console boat on Long Island, NY. Photographed by drone.](https://images.trvl-media.com/place/553248635976481903/93829460-9892-494c-803a-a3af6b3b8523.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

[](https://www.expedia.ca/Hotel-Search?pwaOverlay=map&regionId=553248635976481903)

![Silver Beach map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:mzpyF%60vvxLg%60%40kEi%40%7DHuLaYrBOSaK_Oib%40n%40cFuWiStCmEvBXxDwDfHH%7EK%60NpNxDjFyGlHrAf%5CwSlg%40oUhImBpAvPoN%7El%40kp%40dsAcAxK&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=LI215i5nbJyDKLk8XZgKcAhItxY=)

### Silver Beach

Silver Beach offers a tranquil coastal retreat on Shelter Island with direct access to the sound. This charming area features weathered cottages and natural shorelines perfect for peaceful waterfront strolls. Shell Beach provides a serene spot for swimming and sunbathing. The neighborhood's calm waters make it ideal for kayaking and small boat activities. Enjoy the scent of salt air mixed with pine and beach roses. Most visitors bring supplies or travel to nearby island markets since Silver Beach maintains its residential character.

[See properties](https://www.expedia.ca/Hotel-Search?regionId=553248635976481903)

![Welcome To The Beach. Driftwood beach hut with handwritten welcome sign. Port Crescent State Park. Port Austin, Michigan.](https://images.trvl-media.com/place/553248635976481214/0fd5766e-1ec1-4630-87ca-616953333ece.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

[](https://www.expedia.ca/Hotel-Search?pwaOverlay=map&regionId=553248635976481214)

![Menantic Creek map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:q%7BryFh%7CqxLeOkr%40fT_EnMqEjKc%40fGjBhAuArItErIPrBnB%7DAb%5Cm_AnW&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=wL_I5E54rllE0bcZHkxAdQylRUE=)

### Menantic Creek

Menantic Creek on Shelter Island offers a peaceful waterfront escape where natural beauty takes centre stage. This residential haven features classic Hamptons-style homes with private docks nestled among mature trees. The winding creek waters create a tranquil backdrop for a truly authentic island experience. The area provides excellent opportunities for kayaking, paddleboarding, and birdwatching along pristine shorelines. Visitors can easily explore nearby attractions like Wades Beach and Shelter Island Historical Society. Those seeking quiet relaxation will appreciate the gentle creek sounds and salt-tinged air that define this serene coastal retreat.

[See properties](https://www.expedia.ca/Hotel-Search?regionId=553248635976481214)

![A sweeping view of the natural beauty at Mashomack Preserve on Shelter Island which is situated between the North and South Forks of Long Island, New York.](https://images.trvl-media.com/place/553248635976480820/ef16583d-a1b3-4f29-8d9e-0f21fcceaafc.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

[](https://www.expedia.ca/Hotel-Search?pwaOverlay=map&regionId=553248635976480820)

![Coecles Harbor map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:ybxyFxymxLw%5Das%40rjAyyBnqA%7Cx%40pIl%7E%40%7DhCnt%40&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=xFWty9iq-ZDYNo-RgTcjrckcozE=)

### Coecles Harbor

Coecles Harbour offers a peaceful retreat where pristine waterfront paths wind along Peconic Bay. Luxury yachts and sailboats dot the protected marina, creating a classic New England coastal scene. Wooden docks extend into calm waters, providing perfect sunset viewing spots. This upscale Shelter Island area balances authentic maritime character with vacation amenities. Visitors can enjoy swimming at Menhadden Lane Beach or explore by kayak and paddleboard. The quiet atmosphere, with only the sounds of lapping waves and seabirds, makes it ideal for those seeking a serene coastal escape.

[See properties](https://www.expedia.ca/Hotel-Search?regionId=553248635976480820)

![view of wetland from the Marine Park Salt Marsh Nature Trail in brooklyn, new york (with gil hodges bridge to the rockaways int he background) cloud reflections in bay, water (shell bank creek)](https://images.trvl-media.com/place/553248635976470037/504e907d-021d-4378-950f-32bb724622a2.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

[](https://www.expedia.ca/Hotel-Search?pwaOverlay=map&regionId=553248635976470037)

![Hay Beach map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:q%7DyyFvxoxLu%7B%40aS%7Ei%40owAnj%40cEfEdc%40a_%40nmA&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=oUw1-B9agSYZdTPReexAj0cx418=)

### Hay Beach

Hay Beach offers a tranquil peninsula retreat on Shelter Island, away from the bustling Hamptons scene. This residential haven is surrounded by water on three sides with several beach access points for scenic coastal views. Private waterfront homes and cottages create a peaceful atmosphere where natural beauty takes centre stage. Visitors can explore Menhadden Lane Beach or take short trips to nearby Gardiner's Bay Country Club. The neighborhood's charm lies in its uncrowded shoreline paths and pristine waters. Perfect for kayaking, swimming, and sunset watching, Hay Beach delivers a genuine low-key coastal experience.

[See properties](https://www.expedia.ca/Hotel-Search?regionId=553248635976470037)

![Aerial Views of Mamaroneck, New Rochelle, and Larchmont](https://images.trvl-media.com/place/553248635976481937/9210af7b-6de4-447d-b525-19512b2b53b1.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

[](https://www.expedia.ca/Hotel-Search?pwaOverlay=map&regionId=553248635976481937)

![Shorewood map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:iepyFdhnxLeP%7DEwBi%5Cha%40wNvL%7BLRhb%40cTnSsE%60I&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=qbvaos58sMF0pgaReQcoKBoiPaw=)

### Shorewood

Shorewood offers a peaceful retreat on Shelter Island with pristine shorelines and scenic waterfront paths. Classic Hamptons-style cottages with cedar shingles and white trim line the quiet, tree-lined streets. The neighborhood's charm lies in its natural beauty and exclusive residential character. Wades Beach beckons with sandy shores and calm bay waters perfect for swimming and kayaking. Visitors appreciate the minimal tourist crowds and opportunities for stargazing at night. The salt air mingles with pine scents while gentle waves create a soothing natural soundtrack.

[See properties](https://www.expedia.ca/Hotel-Search?regionId=553248635976481937)

## Stay near popular Shelter Island attractions

![Colorful pebbles and shells on a beach](https://images.trvl-media.com/place/553248621554204761/5a57054c-a374-4fe2-8982-2385bf184bb1.jpg)

### Shell Beach

Why not spend a carefree afternoon at Shell Beach during your travels in Shelter Island? Amble around the area's parks or experience its museums. 

[See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=553248621554204761)

![Man watching sailboat on Long Island Sound](https://images.trvl-media.com/place/553248621554204759/ee48f50e-5c27-4bcd-8a17-a99baf567092.jpg)

### Wades Beach

Why not spend a carefree afternoon at Wades Beach during your travels in Shelter Island? Amble around the area's parks or experience its museums. 

[See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=553248621554204759)

### Gardiner's Bay Country Club

Enjoy a round of golf in Shelter Island at Gardiner's Bay Country Club. Stroll along the area's waterfront or simply enjoy its wineries. 

[See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=6282173)

### Shelter Island Whale's Tail

You can take time to visit Shelter Island Whale's Tail during your travels to Shelter Island. Wander the beaches and waterfront in the area. 

[See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=553248621554204762)

### Mashomack Preserve

Explore the great outdoors at Mashomack Preserve, a lovely green space in Shelter Island. Stroll along the beaches or discover the sunsets in this family-friendly area. 

[See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=6224462)

### Shelter Island Historical Society

You can spend time studying the exhibits at Shelter Island Historical Society during your trip to Shelter Island. Stroll along the beaches or experience the area's museums. 

[See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=553248635961235094)

### Havens House

You can spend an afternoon browsing the exhibits at Havens House during your trip to Shelter Island. Stroll along the area's beaches or simply enjoy its wineries. 

[See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=6232745)

### Menhadden Lane Beach

Why not spend a carefree afternoon at Menhadden Lane Beach during your travels in Shelter Island Heights? 

[See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=553248621554204760)

## Learn more about Shelter Island

Nestled between Long Island's forks, this serene island offers pristine beaches and kayaking through Mashomack Preserve's coastal wetlands. Rent bikes to explore historic mansions and stop at Sunset Beach for seafood with spectacular evening views across Shelter Bay.

[See all hotels in Shelter Island](https://www.expedia.ca/Hotel-Search?startDate=2026-03-29&endDate=2026-03-30&adults=2&regionId=157359)

![Central Park summer](https://images.trvl-media.com/place/157359/6c674470-f02c-495a-ad05-e592d3be267f.jpg?impolicy=fcrop&w=900&h=430&p=1&q=high)

## Top Shelter Island Hotel Reviews

## Recent Reviews in Shelter Island

![The Shoals Suites and Slips](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/5a27472c_y.jpg)

### The Shoals Suites and Slips

6/10 Okay

"Fine "

[](https://expedia.ca/Southold-Hotels-The-Shoals-Suites-And-Slips.h76716269.Hotel-Information)

![The Harbor Front Inn](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/2c9cc7e9_y.jpg)

### The Harbor Front Inn

8/10 Good

"Convenient location in downtown Greenport. Not sure what the “resort fee” was for other than a way to jack up room price. Skip the continental breakfast. Weak. "

[](https://expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information)

![Saybrook Point Resort & Marina](https://images.trvl-media.com/lodging/1000000/40000/38800/38715/fce2d4ec_y.jpg)

### Saybrook Point Resort & Marina

8/10 Good

"Every thing was comfortable and relaxing"

[](https://expedia.ca/Old-Saybrook-Hotels-Saybrook-Point-Resort-Marina.h38715.Hotel-Information)

![The Preston House & Hotel](https://images.trvl-media.com/lodging/22000000/21830000/21825900/21825843/6a60f683_y.jpg)

### The Preston House & Hotel

10/10 Excellent

"The staff were gentle and kind. The room was spacious and clean. The free breakfast was also good."

[](https://expedia.ca/Riverhead-Hotels-The-Preston-House-Hotel.h21825843.Hotel-Information)

![Quality Inn Old Saybrook - Westbrook](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/228c4607_y.jpg)

### Quality Inn Old Saybrook - Westbrook

10/10 Excellent

"nice area and quiet...eat and drink in the same place"

[](https://expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.Hotel-Information)

![Water's Edge Resort & Spa](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/fc6ee41c_y.jpg)

### Water's Edge Resort & Spa

10/10 Excellent

"Excellent place to stay, water view "

[](https://expedia.ca/Old-Saybrook-Hotels-Waters-Edge-Resort-Spa.h9679841.Hotel-Information)

![The Sagaponack](https://images.trvl-media.com/lodging/82000000/81150000/81143200/81143153/ce84672e_y.jpg)

### The Sagaponack

10/10 Excellent

"Very charming, I stayed in one of the cottages, comfortable and well equipped."

[](https://expedia.ca/Wainscott-Hotels-The-Wainscott-Inn.h81143153.Hotel-Information)

![The Bentley Hotel Southampton](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/cc53a2c2_y.jpg)

### The Bentley Hotel Southampton

10/10 Excellent

"Clean room. The man at the office was very friendly."

[](https://expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.Hotel-Information)

![Pier Blue Inn Old Saybrook - Essex](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/5cb2e3e0_y.jpg)

### Pier Blue Inn Old Saybrook - Essex

6/10 Okay

"Very welcoming staff. Average accommodations but comfortable and convenient to supermarket. "

[](https://expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information)

## More cheap stays in Shelter Island

![Pier Blue Inn Old Saybrook - Essex](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/5cb2e3e0_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT

CA $110

CA $126 total

Mar 16 - Mar 17

includes taxes & fees

8/10 Very Good! (1,000 reviews)

[](https://expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information)

![Quality Inn Old Saybrook - Westbrook](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/228c4607_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Quality Inn Old Saybrook - Westbrook

100 Essex Rd Old Saybrook CT

CA $127

CA $146 total

Mar 22 - Mar 23

includes taxes & fees

7.8/10 Good! (1,002 reviews)

[](https://expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.Hotel-Information)

![The Niantic Inn](https://images.trvl-media.com/lodging/16000000/15010000/15001900/15001889/2d17124a_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### The Niantic Inn

345 Main Street Niantic CT

CA $158

CA $182 total

Mar 16 - Mar 17

includes taxes & fees

9.2/10 Wonderful! (143 reviews)

[](https://expedia.ca/Niantic-Hotels-The-Niantic-Inn.h15001889.Hotel-Information)

![The Bentley Hotel Southampton](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/cc53a2c2_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### The Bentley Hotel Southampton

161 Hills Station Rd Southampton NY

CA $176

CA $202 total

Mar 16 - Mar 17

includes taxes & fees

9.6/10 Exceptional! (446 reviews)

[](https://expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.Hotel-Information)

![The Atlantic Hotel](https://images.trvl-media.com/lodging/1000000/450000/447900/447803/ad346ab6_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### The Atlantic Hotel

1655 County Road 39 Southampton NY

CA $156

CA $213 total

Mar 24 - Mar 25

includes taxes & fees

7.2/10 Good! (985 reviews)

[](https://expedia.ca/Southampton-Hotels-The-Atlantic-Hotel.h447803.Hotel-Information)

![Offshore Montauk](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/6944012d_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Offshore Montauk

71 S Emerson Ave Montauk NY

CA $177

CA $281 total

Mar 16 - Mar 17

includes taxes & fees

9.4/10 Exceptional! (115 reviews)

[](https://expedia.ca/Montauk-Hotels-The-Offshore.h113578409.Hotel-Information)

## Hotels in Shelter Island with star rating

![5 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/25600/25559/c6e0103a_z.jpg)

5 Star Hotels

2 properties

[](https://expedia.ca/5Star-Shelter-Island-Hotels.s50-0-d157359.Travel-Guide-Filter-Hotels)

![4 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/23700/23677/6ae928dd_z.jpg)

4 Star Hotels

58 properties

[](https://expedia.ca/4Star-Shelter-Island-Hotels.s40-0-d157359.Travel-Guide-Filter-Hotels)

![3 Star Hotels](https://images.trvl-media.com/lodging/20000000/19690000/19681400/19681371/84fffc75_z.jpg)

3 Star Hotels

272 properties

[](https://expedia.ca/3Star-Shelter-Island-Hotels.s30-0-d157359.Travel-Guide-Filter-Hotels)

![2 Star Hotels](https://images.trvl-media.com/lodging/92000000/91830000/91828000/91827910/6717a2ac_z.jpg)

2 Star Hotels

277 properties

[](https://expedia.ca/2Star-Shelter-Island-Hotels.s20-0-d157359.Travel-Guide-Filter-Hotels)

## Find out more about Shelter Island

### Top reasons to visit Shelter Island

- **Stunning Beaches:**  Shelter Island boasts beautiful beaches like Crescent Beach, perfect for relaxation and ocean views.
- **Outdoor Adventures:**  Enjoy paddle boarding, windsurfing, and golf amidst the island's natural beauty.
- **Rich History:**  Explore historic buildings and learn about the island's unique heritage.
- **Scenic Boat Tours:**  Take a picturesque boat tour to appreciate the stunning coastal scenery.
- **Diverse Accommodations:**  Choose from pet-friendly and family-oriented stays to suit every traveller's needs.

### Find great hotels near Shelter Island

Experience the charm of Shelter Island with a variety of accommodations tailored to meet the needs of every traveller. From pet-friendly options to family-oriented stays, you'll find the perfect lodging for your adventure. Explore the best hotels and luxury accommodations that provide a memorable vacation experience amidst the beautiful surroundings of Shelter Island.

- **[Sound View Greenport: ](https://www.expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information)** Nestled 6.4km from Shelter Island, Sound View Greenport is a delightful 3.5-star hotel that combines a business-friendly environment with a family-oriented beach getaway. Guests can enjoy direct access to the pristine beach, perfect for sun-soaked days. The hotel is equipped with essential business amenities, including meeting rooms and conference spaces, ensuring a productive stay for corporate travellers. Families will appreciate thoughtful features such as window guards for children and complimentary cribs, making it a safe and enjoyable destination for all ages.
- **[Sag Harbor Inn: ](https://www.expedia.ca/Sag-Harbor-Hotels-Sag-Harbor-Inn.h26497858.Hotel-Information)** Located 8.0km from Shelter Island, Sag Harbor Inn offers a sophisticated 3.5-star experience tailored for business travellers. This charming inn provides essential business facilities, including meeting rooms, allowing guests to conduct meetings in a serene setting. The inn's proximity to both the vibrant town of Sag Harbor and the scenic waterfront makes it an appealing choice for those looking to blend work and leisure. The inviting atmosphere and convenient amenities make it a great option for a productive yet relaxing stay.
- **[The Harbor Front Inn: ](https://www.expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information)** Situated 4.8km from Shelter Island, The Harbor Front Inn is a welcoming 3.5-star hotel that prides itself on being pet-friendly. Ideal for business travellers who wish to bring their furry companions along, the inn features a pet policy that allows dogs in guest rooms. With a focus on comfort and convenience, guests can enjoy business amenities while also having the flexibility to travel with their pets. The charming waterfront location enhances the appeal, ensuring a delightful retreat for both you and your four-legged friends.

### Where to stay near Shelter Island

Discover the charm of Shelter Island, a perfect getaway for outdoor enthusiasts and couples alike. Enjoy stunning ocean views and relaxing beach access at Crescent Beach. Explore the rich history of the area while immersing yourself in its family-friendly atmosphere. Nearby Long Island offers additional excursions and scenic spots, making Shelter Island an ideal base for your vacation adventure. Experience the unique blend of relaxation and exploration that this picturesque destination has to offer.

- **[Hamptons: ](https://www.expedia.ca/Hamptons-Hotels.d6056452.Travel-Guide-Hotels)** Located 14.5km from Shelter Island, the Hamptons is a quintessential summer retreat known for its stunning beaches and vibrant atmosphere. This area is particularly popular from June to August, attracting visitors for its romantic seaside charm and outdoor activities. With picturesque golf courses and lively music concerts, the Hamptons offers an array of entertainment options. Local landmarks like beautiful beaches and serene lakes provide the perfect backdrop for relaxation and adventure alike, making it an ideal spot for those looking to soak up the sun and enjoy coastal life.
- **[Greenport: ](https://www.expedia.ca/Greenport-Hotels.d110728.Travel-Guide-Hotels)** Only 4.8km away from Shelter Island, Greenport boasts a charming small-town vibe combined with rich maritime history. This city, which sees a spike in visitors from June to August, is perfect for those seeking outdoor adventures, romantic getaways, and beach time. Visitors can enjoy various activities like golfing and attending local music concerts. The nearby family-friendly beaches and event conference venues add to the allure, making Greenport a delightful destination for exploration and fun.
- **[Sag Harbor: ](https://www.expedia.ca/Sag-Harbor-Hotels.d154327.Travel-Guide-Hotels)** Just 8.0km from Shelter Island, Sag Harbor is a picturesque village that captures the essence of coastal living. Known for its outdoor attractions and romantic atmosphere, this city experiences peak visitor numbers in the summer months. Visitors can indulge in golfing or even skiing during the winter months. The local beaches and parks offer ample opportunities for relaxation and recreation, making Sag Harbor a charming stop for those looking to immerse themselves in the beauty of the East End.

### Things to do in and around Shelter Island

Shelter Island is perfect for outdoor adventures and romantic getaways, offering a variety of activities. Enjoy paddle boarding and windsurfing on its beautiful waters, explore numerous attractions, or take a scenic boat tour. Golf enthusiasts will appreciate the island's golf courses, and there are opportunities for skiing as well. With its stunning beaches and natural beauty, Shelter Island is an ideal destination for a memorable vacation.

**Shopping**

The [Greenport Farmers' Market](https://www.expedia.ca/Greenport-Farmers-Market-Hotels.0-l553248621532665744-0.Travel-Guide-Filter-Hotels), located 4.8km away, offers a vibrant public market experience with local produce and crafts. [The Style Bar](https://www.expedia.ca/The-Style-Bar-Hotels.0-l553248621532665737-0.Travel-Guide-Filter-Hotels) and [BookHampton](https://www.expedia.ca/BookHampton-Hotels.0-l553248621532665731-0.Travel-Guide-Filter-Hotels), both 8.0km away, feature unique clothing and books, perfect for souvenirs. If you're up for a drive, explore further shopping options in nearby towns.

**Recreation**

[Shelter Island Whale's Tail](https://www.expedia.ca/Shelter-Island-Whales-Tail-Hotels.0-l553248621554204762-0.Travel-Guide-Filter-Hotels) offers a fun-filled mini-golf experience with a family-friendly atmosphere perfect for playful competition. For golf enthusiasts, [Noyac Golf Club](https://www.expedia.ca/Noyac-Golf-Club-Hotels.0-l6064499-0.Travel-Guide-Filter-Hotels) presents a picturesque outdoor course just 9.7km away. [Cedar Point County Park](https://www.expedia.ca/Cedar-Point-County-Park-Hotels.0-l6326834-0.Travel-Guide-Filter-Hotels), located 8.0km away, invites relaxation amidst nature with its tranquil surroundings.

**Adventure**

Experience the thrill at [Splish Splash Water Park](https://www.expedia.ca/Splish-Splash-Water-Park-Hotels.0-l6173416-0.Travel-Guide-Filter-Hotels), located 37.0km from Shelter Island, with exciting water slides and family fun. Hike the scenic [Walking Dunes Trailhead](https://www.expedia.ca/Walking-Dunes-Trailhead-Hotels.0-l553248633992587102-0.Travel-Guide-Filter-Hotels), 25.7km away, for stunning views. For adrenaline, check out the [Riverhead Raceway](https://www.expedia.ca/Riverhead-Raceway-Hotels.0-l6173429-0.Travel-Guide-Filter-Hotels), 35.4km from Shelter Island, featuring exhilarating motor racing.

**Nightlife**

Experience the enchanting [Greenport Carousel](https://www.expedia.ca/Greenport-Carousel-Hotels.0-l553248635961252285-0.Travel-Guide-Filter-Hotels), just 4.8km away, for a nostalgic ride under the stars. For a cultural evening, visit [Bay Street Theatre](https://www.expedia.ca/Bay-Street-Theatre-Hotels.0-l6326787-0.Travel-Guide-Filter-Hotels), 8.0km from Shelter Island, which offers a blend of romance and entertainment, perfect for families and couples alike.

\*Distances are measured in a straight line; actual driving distances may vary depending on the route.

### Booking tips and Expedia advantages for Shelter Island

To save money on your trip to Shelter Island, consider visiting between January and March when hotel prices are at their lowest. Tuesdays are typically the least expensive days for accommodation. Use Expedia to search for budget-friendly hotels, and don’t forget to check for eco-certified options. Additionally, bundling your hotel with flights and activities can lead to great savings. Explore free local attractions and utilize public transport to keep costs down. Planning your visit during the off-peak season and taking advantage of deals will enhance your experience without breaking the bank.

- **The most and least expensive months on average to stay in a hotel:**  The hotel pricing in Shelter Island is moderately seasonal. The cheapest months to stay in Shelter Island are January to March, where the prices are moderately lower. This is in comparison to June to August, where prices are moderately higher.
- **The most and least expensive days on average to stay in a hotel:**  The least expensive day to stay in Shelter Island is Tuesday. The most expensive day to stay in Shelter Island is Saturday.
- **Find cheap hotels on Expedia:**  Expedia’s search tool enables you to specify your budget, desired location, and additional preferences. You can arrange your search results to display prices from lowest to highest, ensuring you see the most affordable hotels first. Additionally, you have the option to refine your search by hotel type; for instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels that are available for booking.
- **Consider bundling your trip:**  You can save money by combining your Shelter Island hotel reservation with your flights and activities through an Expedia package.

### Find the best attractions in and around Shelter Island

Shelter Island offers a perfect blend of outdoor adventures, romantic getaways, and family-friendly experiences. Visitors can enjoy beautiful beaches, explore historic buildings, and relax in urban parks. With a focus on culture and leisure, popular activities include unwinding at sunset beach, making it an ideal destination for those seeking relaxation and exploration.

- **[67 Steps Beach: ](https://www.expedia.ca/67-Steps-Beach-Hotels.0-l553248626388140598-0.Travel-Guide-Filter-Hotels)** A picturesque beach located 6.4km from Shelter Island, 67 Steps Beach offers a serene escape with its beautiful shoreline and tranquil vibes. It's the perfect spot for sunbathing, swimming, or simply enjoying the coastal scenery.
- **[Gardiner's Bay Country Club: ](https://www.expedia.ca/Gardiners-Bay-Country-Club-Hotels.0-l6282173-0.Travel-Guide-Filter-Hotels)** Situated within Shelter Island, this exceptional golf course provides a unique blend of challenging play and stunning views. Experience a round of golf surrounded by lush landscapes and the refreshing breeze from the bay.
- **[Orient Point County Park: ](https://www.expedia.ca/Orient-Point-County-Park-Hotels.0-l553248621532665781-0.Travel-Guide-Filter-Hotels)** Located 12.9km from Shelter Island, this urban park is ideal for families and outdoor enthusiasts. Enjoy scenic trails, picnic spots, and the vibrant atmosphere of the city, making it a great place to unwind and connect with nature.

### Best time to go to Shelter Island

The best time to visit Shelter Island is dependant on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain. 

| **![calendar](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** |
| ---------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------- | ------------------------------------------------------------------------------------------------------------- |
| January                                                                                                          | 35.6°F (2.0°C)                                                                                                       | Light Rain                                                                                                       | Mostly Sunny                                                                                                                 | Average                                                                                                        | Moderately Low                                                                                                |
| February                                                                                                         | 35.8°F (2.1°C)                                                                                                       | Light Rain                                                                                                       | Mostly Cloudy                                                                                                                | Average                                                                                                        | Moderately Low                                                                                                |
| March                                                                                                            | 39.7°F (4.3°C)                                                                                                       | Light Rain                                                                                                       | Mostly Sunny                                                                                                                 | Average                                                                                                        | Moderately Low                                                                                                |
| April                                                                                                            | 47.5°F (8.6°C)                                                                                                       | Light Rain                                                                                                       | Mostly Sunny                                                                                                                 | Average                                                                                                        | Average                                                                                                       |
| May                                                                                                              | 55.8°F (13.2°C)                                                                                                      | Light Rain                                                                                                       | Mostly Sunny                                                                                                                 | Average                                                                                                        | Average                                                                                                       |
| June                                                                                                             | 64.9°F (18.3°C)                                                                                                      | Light Rain                                                                                                       | Mostly Sunny                                                                                                                 | High                                                                                                           | Moderately High                                                                                               |
| July                                                                                                             | 73.0°F (22.8°C)                                                                                                      | Light Rain                                                                                                       | Mostly Sunny                                                                                                                 | High                                                                                                           | Moderately High                                                                                               |
| August                                                                                                           | 73.4°F (23.0°C)                                                                                                      | Light Rain                                                                                                       | Mostly Sunny                                                                                                                 | High                                                                                                           | Moderately High                                                                                               |
| September                                                                                                        | 68.2°F (20.1°C)                                                                                                      | Light Rain                                                                                                       | Mostly Sunny                                                                                                                 | Average                                                                                                        | Average                                                                                                       |
| October                                                                                                          | 59.7°F (15.4°C)                                                                                                      | Light Rain                                                                                                       | Mostly Sunny                                                                                                                 | Low                                                                                                            | Average                                                                                                       |
| November                                                                                                         | 49.6°F (9.8°C)                                                                                                       | Light Rain                                                                                                       | Mostly Sunny                                                                                                                 | Low                                                                                                            | Average                                                                                                       |
| December                                                                                                         | 42.1°F (5.6°C)                                                                                                       | Light Rain                                                                                                       | Mostly Cloudy                                                                                                                | Low                                                                                                            | Average                                                                                                       |

### The nearest major airports for your trip to Shelter Island

To reach Shelter Island, New York, you have several airport options. Islip, NY ([ISP](https://www.expedia.ca/MacArthur-Airport-Hotels.0-aISP-0.Travel-Guide-Filter-Hotels)\-MacArthur) is situated 70.8km away, with nearby accommodations like the 3.5-star [Hyatt Regency Long Island](https://www.expedia.ca/Hauppauge-Hotels-Hyatt-Regency-Long-Island.h3668.Hotel-Information) and Jake's 58 Casino Hotel, both 6.4km from the airport, along with the [Radisson Hotel Hauppauge-Long Island](https://www.expedia.ca/Hauppauge-Hotels-Radisson-Hotel-Hauppauge-Long-Island.h10706.Hotel-Information), 14.5km away. New Haven, CT ([HVN](https://www.expedia.ca/Tweed-New-Haven-Regional-Airport-Hotels.0-aHVN-0.Travel-Guide-Filter-Hotels)\-Tweed - New Haven Regional) is 51.5km from Shelter Island, offering excellent hotels such as [The Blake Hotel](https://www.expedia.ca/New-Haven-Hotels-The-Blake-Hotel.h32129620.Hotel-Information), [Graduate by Hilton New Haven](https://www.expedia.ca/New-Haven-Hotels-Graduate-New-Haven.h37200005.Hotel-Information), and [Omni New Haven Hotel at Yale](https://www.expedia.ca/New-Haven-Hotels-Omni-New-Haven-Hotel-At-Yale.h49957.Hotel-Information), all 4.8km from the airport. East Hampton, NY ([HTO](https://www.expedia.ca/East-Hampton-Airport-Hotels.0-aHTO-0.Travel-Guide-Filter-Hotels)) is the closest at 14.5km away, featuring the 5-star [Mill House Inn](https://www.expedia.ca/East-Hampton-Hotels-Mill-House-Inn.h2861838.Hotel-Information) and the 4.5-star [Topping Rose House](https://www.expedia.ca/Bridgehampton-Hotels-Topping-Rose-House.h5581380.Hotel-Information), both 4.8km from the airport.

## Frequently asked questions

### What is the best area to stay in Shelter Island?

> Shelter Island Heights is the island's commercial centre, offering a mix of shops, restaurants, and hotels. It's well-connected by ferry to Greenport on the North Fork, making it an ideal base for exploring both sides of the Peconic Bay. The area is very walkable, with most establishments clustered around the main streets leading from the ferry terminal.
> 
>   
> For couples seeking a refined and relaxed getaway, Shelter Island Heights offers elegant boutique hotels and fine dining options. You'll find art galleries and charming local shops, great for leisurely strolls. The easy access to the ferry also makes day trips to Greenport's vineyards and breweries very straightforward.
> 
>   
> Families will also appreciate Shelter Island Heights for its practical location. There are ice cream parlours and family-friendly eateries within easy reach.

### What are the best family hotels in Shelter Island?

> This highly-rated hotel, with a 9.2 review score, is particularly well-suited for families. It offers a range of family-friendly amenities including complimentary cots, beach toys, and games for children. There is also onsite babysitting and childcare services available, providing convenience for parents. The hotel is incredibly well-located, being just 0.1 km from Sunset Beach and 0.5 km from Crescent Beach, making it easy to enjoy the local surroundings. Find more [child-friendly accommodations in Shelter Island](https://www.expedia.ca/Shelter-Island-Hotels-Family-Hotel.0-0-d157359-tFamilyHotel.Travel-Guide-Filter-Hotels)

### What are the best spa hotels in Shelter Island?

> This hotel, with a superb 9.2 rating, offers a wonderful range of amenities to enhance your spa experience. Guests can enjoy massages on the beach, as well as general massage services, and the rooms feature designer toiletries, Frette Italian sheets, luxurious bathrobes, and comfortable premium bedding. The hotel also provides champagne service and air conditioning for added comfort. It is conveniently located just 0.5 km from Crescent Beach and 0.7 km from Shelter Island Country Club. See all [spa hotels in Shelter Island](https://www.expedia.ca/Shelter-Island-Hotels-Spa-Hotel.0-0-d157359-tSpaHotel.Travel-Guide-Filter-Hotels)

### What are the top pet-friendly hotels in Shelter Island?

> The Sunset Beach Hotel, with an excellent rating of 9.2, is highly recommended for travellers with pets. It not only permits pets but also provides thoughtful amenities such as food and water bowls, ensuring your furry companions are well catered for. The hotel is wonderfully located, just 0.1 km from Sunset Beach and 0.5 km from Crescent Beach, offering easy access for walks and seaside enjoyment. Guests can also indulge in massages on the beach, adding to a relaxing stay for both you and your pet. See more [pet-friendly hotels in Shelter Island](https://www.expedia.ca/Shelter-Island-Hotels-Pet-Friendly-Hotel.0-0-d157359-tPetfriendlyHotel.Travel-Guide-Filter-Hotels)

### What are the best budget hotels in Shelter Island?

> This hotel, with a superb 9.2 rating, offers complimentary WiFi and free self-parking, which adds to its value. Guests can also enjoy massages directly on the beach, providing a relaxing experience. Its location is a key highlight, being just 0.1 km from Sunset Beach and 0.5 km from Crescent Beach, making it very convenient for beach lovers. View all [budget hotels in Shelter Island](https://www.expedia.ca/Shelter-Island-Hotels-Cheap-Hotels.0-0-d157359-tCheapHotels.Travel-Guide-Filter-Hotels)

### What are the best hotels in Shelter Island near Crescent Beach?

> This highly-rated hotel, with a superb 9.2 review score, is conveniently located just 0.5 km from Crescent Beach. It is also only 0.1 km from Sunset Beach. Guests with families will like the range of amenities, including free cribs, beach toys, and other toys and games specifically for children. On-site babysitting and childcare services are also available, providing added convenience for parents.

### When is the best time to go to Shelter Island?

> For those seeking a classic summer holiday experience, July and August offer the warmest temperatures, superb for enjoying the beaches and water activities. You'll find all the restaurants and shops open, and there's a lively, yet relaxed, atmosphere across the island. This period is ideal for families and couples looking for a traditional seaside escape with plenty of sunshine.
> 
>   
> If you prefer a slightly quieter visit with pleasant weather and fewer crowds, late May and early June, or early September, are also excellent choices. The weather is still lovely, most establishments are open, and you can experience the island's natural beauty with a bit more tranquility.

### Can I cancel my hotel reservation on Expedia?

### How can I save on a Shelter Island hotel booking with Expedia?

### How much is the nightly rate at a Shelter Island hotel?

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- [Silver Beach Hotels ](https://www.expedia.ca/Silver-Beach-Shelter-Island-Hotels.0-n553248635976481903-0.Travel-Guide-Filter-Hotels)
- [Cheap Hotels in Southold ](https://www.expedia.ca/Southold-Hotels-Cheap-Hotels.0-0-d183719-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Romantic Hotels in Southold ](https://www.expedia.ca/Southold-Hotels-Romantic-Hotel.0-0-d183719-tRomanticHotel.Travel-Guide-Filter-Hotels)
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- [The Heights Hotels ](https://www.expedia.ca/The-Heights-Shelter-Island-Heights-Hotels.0-n553248635976473534-0.Travel-Guide-Filter-Hotels)
- [Hotels near Wades Beach ](https://www.expedia.ca/Wades-Beach-Hotels.0-l553248621554204759-0.Travel-Guide-Filter-Hotels)

- [Flights to Greenport ](https://www.expedia.ca/Cheap-Flights-To-Greenport.d110728.Travel-Guide-Flights)
- [Flights to Sag Harbor ](https://www.expedia.ca/Cheap-Flights-To-Sag-Harbor.d154327.Travel-Guide-Flights)
- [Flights from Southold ](https://www.expedia.ca/lp/flights/183719/flights-from-southold)
- [Flights from North Haven ](https://www.expedia.ca/lp/flights/553248634998589872/flights-from-north-haven)
- [Flights from East Marion ](https://www.expedia.ca/lp/flights/6069914/flights-from-east-marion)
- [Flights from Orient ](https://www.expedia.ca/lp/flights/6326191/flights-from-orient)
- [Flights from Toronto (YYZ) to New York (NYC) ](https://www.expedia.ca/lp/flights/yyz/nyc/toronto-to-new-york)

- [Visit East Marion ](https://www.expedia.ca/East-Marion.dx6069914)
- [Visit Pipes Cove ](https://www.expedia.ca/Greenport-Pipes-Cove.dx553248635976473295)
- [Kontokosta Winery ](https://www.expedia.ca/Kontokosta-Winery-Greenport.d6326928.Vacation-Attraction)
- [Visit North Haven ](https://www.expedia.ca/North-Haven.dx553248634998589872)
- [Orient Vacations ](https://www.expedia.ca/Orient.d6326191.Destination-Travel-Guides)
- [Visit Bay Point ](https://www.expedia.ca/Sag-Harbor-Bay-Point.dx553248635976471151)
- [Sag Harbor Vacations ](https://www.expedia.ca/Sag-Harbor.d154327.Destination-Travel-Guides)
- [Visit Sag Harbor ](https://www.expedia.ca/Sag-Harbor.dx154327)
- [Shelter Island Heights Vacations ](https://www.expedia.ca/Shelter-Island-Heights.d183716.Destination-Travel-Guides)

- [Car rental Greenport ](https://www.expedia.ca/Car-Rentals-In-Greenport.d110728.Car-Rental-Guide)
- [Car rental Orient ](https://www.expedia.ca/Car-Rentals-In-Orient.d6326191.Car-Rental-Guide)
- [Car rental Sag Harbor ](https://www.expedia.ca/Car-Rentals-In-Sag-Harbor.d154327.Car-Rental-Guide)

- [Sag Harbor Vacation Rentals ](https://www.expedia.ca/Sag-Harbor-Vacation-Rentals.d154327.Travel-Guide-VacationRentals)

- [Things to do in Greenport ](https://www.expedia.ca/Things-To-Do-In-Greenport.d110728.Travel-Guide-Activities)
- [Things to do in Sag Harbor ](https://www.expedia.ca/Things-To-Do-In-Sag-Harbor.d154327.Travel-Guide-Activities)
- [Things to do in Shelter Island Heights ](https://www.expedia.ca/Things-To-Do-In-Shelter-Island-Heights.d183716.Travel-Guide-Activities)

- [Book Hotels in Shelter Island on Expedia.com ](https://www.expedia.com/Shelter-Island-Hotels.d157359.Travel-Guide-Hotels)

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