Title: 4 Stars Hotels in Shelter Island Heights, New York from CA $261 - Find Cheap Shelter Island Heights Hotels With 4 Stars | Expedia.ca

[Shelter Island Heights Travel Guide](https://expedia.ca/Shelter-Island-Heights.dx183716)[Hotels in Shelter Island Heights](https://expedia.ca/Shelter-Island-Heights-Hotels.d183716.Travel-Guide-Hotels)[Vacation Rentals in Shelter Island Heights](https://expedia.ca/Shelter-Island-Heights-Vacation-Rentals.d183716.Travel-Guide-VacationRentals)[Flights to Shelter Island Heights](https://expedia.ca/Cheap-Flights-To-Shelter-Island-Heights.d183716.Travel-Guide-Flights)[Things to do in Shelter Island Heights](https://expedia.ca/Things-To-Do-In-Shelter-Island-Heights.d183716.Travel-Guide-Activities)[Shelter Island Heights Car Rentals](https://expedia.ca/Car-Rentals-In-Shelter-Island-Heights.d183716.Car-Rental-Guide)[Shelter Island Heights Vacation Packages](https://expedia.ca/Shelter-Island-Heights.d183716.Destination-Travel-Guides)

![View of Dering Harbor](https://images.trvl-media.com/place/157359/8df1734b-1204-4cc5-a5a0-67f90d8a76a3.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Brian V. Rowe

![](https://images.trvl-media.com/place/157359/8df1734b-1204-4cc5-a5a0-67f90d8a76a3.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check availability on Shelter Island Heights 4 Star Hotels

Tonight

[Feb 21 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=183716&startDate=2026-02-21&endDate=2026-02-22&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Feb 22 - Feb 23](https://www.expedia.ca/Hotel-Search?regionId=183716&startDate=2026-02-22&endDate=2026-02-23&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=183716&startDate=2026-02-27&endDate=2026-03-01&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=183716&startDate=2026-03-06&endDate=2026-03-08&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Shelter Island Heights 4-star hotels

![Exterior](https://images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/b29cbb53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Ocean View King](https://images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/9241bd8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/0272b9dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Ocean View One Bedroom Suite](https://images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/d3ce4464.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Gurney's Montauk Resort & Seawater Spa

[](https://www.expedia.ca/Montauk-Hotels-Gurneys-Montauk-Resort-Seawater-Spa.h7033726.Hotel-Information)

Montauk

8.4/10

Very good

(729 reviews)

"Room was spotless, staff were great and the resort is top notch!!"

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

Carrie

CA $396

CA $544 total

includes taxes & fees

Feb 22 - Feb 23

[](https://www.expedia.ca/Montauk-Hotels-Gurneys-Montauk-Resort-Seawater-Spa.h7033726.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/1ec18076.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 1 King Bed, Accessible (Roll In Shower)](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/5bf701c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 2 Bedrooms | View from room](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/79675399.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/f4c87c86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Madison Beach Hotel

[](https://www.expedia.ca/Madison-Hotels-Madison-Beach-Hotel.h1209378.Hotel-Information)

Madison Center

9.4/10

Exceptional

(346 reviews)

"Staff and hotel are lovely "

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

Steven

CA $335

CA $386 total

includes taxes & fees

Mar 1 - Mar 2

[](https://www.expedia.ca/Madison-Hotels-Madison-Beach-Hotel.h1209378.Hotel-Information)

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

![Exterior](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/8a4a605e.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)

![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)

### Sound View Greenport

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

Greenport

8.4/10

Very good

(614 reviews)

"Nice place"

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

Mateusz

CA $204

CA $272 total

includes taxes & fees

Mar 23 - Mar 24

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

![2 restaurants, breakfast served](https://images.trvl-media.com/lodging/1000000/10000/7000/6970/c585313b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/10000/7000/6970/d3ed50cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private beach, beach towels, kayaking, fishing](https://images.trvl-media.com/lodging/1000000/10000/7000/6970/021137e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 restaurants, breakfast served](https://images.trvl-media.com/lodging/1000000/10000/7000/6970/f58691c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Montauk Yacht Club

[](https://www.expedia.ca/Montauk-Hotels-Gurneys-Star-Island-Resort-Marina.h6970.Hotel-Information)

Montauk

8.6/10

Excellent

(1,000 reviews)

"Great hotel. Would like to come stay again in the summer."

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

Stefania

[](https://www.expedia.ca/Montauk-Hotels-Gurneys-Star-Island-Resort-Marina.h6970.Hotel-Information)

![Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/84000000/83520000/83519500/83519458/aa9cc8cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby, free beach shuttle, sun loungers, beach umbrellas](https://images.trvl-media.com/lodging/84000000/83520000/83519500/83519458/650853cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Couples treatment rooms, body treatments, hot stone massages](https://images.trvl-media.com/lodging/84000000/83520000/83519500/83519458/1782c2d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Daily cooked-to-order breakfast (USD 25 per person)](https://images.trvl-media.com/lodging/84000000/83520000/83519500/83519458/34ace0dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Canoe Place Inn and Cottages

[](https://www.expedia.ca/Hampton-Bays-Hotels-Canoe-Place-Inn-And-Cottages.h83519458.Hotel-Information)

Hampton Bays

9.8/10

Exceptional

(62 reviews)

"Wonderful stay! "

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

Lindsay

[](https://www.expedia.ca/Hampton-Bays-Hotels-Canoe-Place-Inn-And-Cottages.h83519458.Hotel-Information)

![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/17000000/16550000/16544700/16544673/f1ebef28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/17000000/16550000/16544700/16544673/22da4a39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/17000000/16550000/16544700/16544673/69a951cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/17000000/16550000/16544700/16544673/a44e62eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hero Beach Club

[](https://www.expedia.ca/Montauk-Hotels-Hero-Beach-Club.h16544673.Hotel-Information)

Montauk

9.0/10

Wonderful

(203 reviews)

"Great weekend trip "

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

Timothy

CA $218

CA $388 total

includes taxes & fees

Mar 15 - Mar 16

[](https://www.expedia.ca/Montauk-Hotels-Hero-Beach-Club.h16544673.Hotel-Information)

![Courtyard Balcony King | Courtyard view](https://images.trvl-media.com/lodging/16000000/15410000/15408300/15408228/5e0bc055.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/16000000/15410000/15408300/15408228/966ffb4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Blackout drapes, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/16000000/15410000/15408300/15408228/268528e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/16000000/15410000/15408300/15408228/00b9aef3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Marram

[](https://www.expedia.ca/Montauk-Hotels-Marram.h15408228.Hotel-Information)

Montauk

8.8/10

Excellent

(253 reviews)

"Beautiful resort in a great location "

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

Nikki

[](https://www.expedia.ca/Montauk-Hotels-Marram.h15408228.Hotel-Information)

![View from property](https://images.trvl-media.com/lodging/24000000/23260000/23252100/23252049/52063f27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/24000000/23260000/23252100/23252049/338f251a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 King Bed with Sofa bed](https://images.trvl-media.com/lodging/24000000/23260000/23252100/23252049/7418aad9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/24000000/23260000/23252100/23252049/93f768d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Journey East Hampton

[](https://www.expedia.ca/East-Hampton-Hotels-Journey-East-Hampton.h23252049.Hotel-Information)

East Hampton North

9.2/10

Wonderful

(163 reviews)

"Amazing stay"

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

Liana

CA $238

CA $300 total

includes taxes & fees

Feb 24 - Feb 25

[](https://www.expedia.ca/East-Hampton-Hotels-Journey-East-Hampton.h23252049.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)

![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)

![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/fe6e5945.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

(144 reviews)

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

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

Dan

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

![Beach nearby, white sand, sun loungers, beach umbrellas](https://images.trvl-media.com/lodging/11000000/10550000/10547800/10547745/028711b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/11000000/10550000/10547800/10547745/fa70e85b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Frette Italian sheets, premium bedding, down comforters](https://images.trvl-media.com/lodging/11000000/10550000/10547800/10547745/06408853.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Frette Italian sheets, premium bedding, down comforters](https://images.trvl-media.com/lodging/11000000/10550000/10547800/10547745/a3bdf0f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Roundtree, Amagansett

[](https://www.expedia.ca/Amagansett-Hotels-The-Roundtree.h10547745.Hotel-Information)

Amagansett North

10/10

Exceptional

(93 reviews)

"Very nice property, very nice food, and very nice service. Although the room was very nice and clean there was some maintenance needed in the bathroom area"

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

Francisco

CA $813

CA $976 total

includes taxes & fees

Feb 22 - Feb 23

[](https://www.expedia.ca/Amagansett-Hotels-The-Roundtree.h10547745.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/2000000/1490000/1484300/1484254/a99c206a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury Room, 1 Bedroom, Non Smoking (Room 314)](https://images.trvl-media.com/lodging/2000000/1490000/1484300/1484254/61b576aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury Room, 1 Bedroom, Non Smoking (Room 322)](https://images.trvl-media.com/lodging/2000000/1490000/1484300/1484254/e11ede87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior entrance](https://images.trvl-media.com/lodging/2000000/1490000/1484300/1484254/98c270a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Copper Beech Inn

[](https://www.expedia.ca/Old-Saybrook-Hotels-Copper-Beech-Inn.h1484254.Hotel-Information)

Ivoryton

8.6/10

Excellent

(507 reviews)

"Very nice property. Very clean. Staff was very nice - very good breakfast. "

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

Marilyn

CA $382

CA $439 total

includes taxes & fees

Feb 25 - Feb 26

[](https://www.expedia.ca/Old-Saybrook-Hotels-Copper-Beech-Inn.h1484254.Hotel-Information)

![2 restaurants, American cuisine](https://images.trvl-media.com/lodging/2000000/1090000/1085700/1085655/d3bf1318.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/2000000/1090000/1085700/1085655/d269b9f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/2000000/1090000/1085700/1085655/67db121e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Carriage House | Living area](https://images.trvl-media.com/lodging/2000000/1090000/1085700/1085655/6a224301.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The 1770 House Restaurant & Inn

[](https://www.expedia.ca/East-Hampton-Hotels-The-1770-House-Restaurant-Inn.h1085655.Hotel-Information)

East Hampton

9.8/10

Exceptional

(162 reviews)

"The staff was incredibly genuine and the property felt intimate and comfortable."

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

Aniya

CA $331

CA $452 total

includes taxes & fees

Feb 22 - Feb 23

[](https://www.expedia.ca/East-Hampton-Hotels-The-1770-House-Restaurant-Inn.h1085655.Hotel-Information)

![Outdoor pool](https://images.trvl-media.com/lodging/6000000/5590000/5581400/5581380/8b4b1f10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cottage, 2 Single Beds | View from room](https://images.trvl-media.com/lodging/6000000/5590000/5581400/5581380/9125969a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/6000000/5590000/5581400/5581380/9423d3da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Library](https://images.trvl-media.com/lodging/6000000/5590000/5581400/5581380/88ff99e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Topping Rose House

[](https://www.expedia.ca/Bridgehampton-Hotels-Topping-Rose-House.h5581380.Hotel-Information)

Bridgehampton

9.0/10

Wonderful

(142 reviews)

"Our second home :)"

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

olivia

CA $674

CA $775 total

includes taxes & fees

Mar 24 - Mar 25

[](https://www.expedia.ca/Bridgehampton-Hotels-Topping-Rose-House.h5581380.Hotel-Information)

![Property entrance](https://images.trvl-media.com/lodging/10000000/9660000/9652100/9652095/d7688cb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Classic Queen](https://images.trvl-media.com/lodging/10000000/9660000/9652100/9652095/6ddcc118.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/10000000/9660000/9652100/9652095/968c61db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/10000000/9660000/9652100/9652095/32e03a99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Maidstone

[](https://www.expedia.ca/East-Hampton-Hotels-The-Maidstone.h9652095.Hotel-Information)

East Hampton

8.0/10

Very good

(150 reviews)

"We had a wonderful stay "

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

Sabrina

CA $228

CA $261 total

includes taxes & fees

Feb 26 - Feb 27

[](https://www.expedia.ca/East-Hampton-Hotels-The-Maidstone.h9652095.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)

![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)

![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)

![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/7000000/6480000/6473500/6473437/f53e135a.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)

![Aerial view](https://images.trvl-media.com/lodging/32000000/31010000/31007600/31007589/4db6535f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/32000000/31010000/31007600/31007589/bbbb0bf2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby](https://images.trvl-media.com/lodging/32000000/31010000/31007600/31007589/6809b461.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Aerial view](https://images.trvl-media.com/lodging/32000000/31010000/31007600/31007589/d9c11af0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### East Hampton Art House Bed & Breakfast

[](https://www.expedia.ca/East-Hampton-Hotels-East-Hampton-Art-House-Bed-Breakfast.h31007589.Hotel-Information)

Clearwater Beach

9.6/10

Exceptional

(65 reviews)

"The hosts were really nice and the breakfast is excellent!"

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

IVAN

[](https://www.expedia.ca/East-Hampton-Hotels-East-Hampton-Art-House-Bed-Breakfast.h31007589.Hotel-Information)

![Miss Anna James Room](https://images.trvl-media.com/lodging/79000000/78200000/78191100/78191036/w848h631x48y3-ad11e9c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/79000000/78200000/78191100/78191036/f09f38b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Katharine Hepburn Room](https://images.trvl-media.com/lodging/79000000/78200000/78191100/78191036/20c673f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/79000000/78200000/78191100/78191036/1891e70e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### James Pharmacy Bed & Breakfast

[](https://www.expedia.ca/Old-Saybrook-Hotels-James-Pharmacy-Bed-Breakfast.h78191036.Hotel-Information)

Old Saybrook Center

9.0/10

Wonderful

(23 reviews)

"Cute B&B, very nice room, check-in worked well"

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

Isolde

[](https://www.expedia.ca/Old-Saybrook-Hotels-James-Pharmacy-Bed-Breakfast.h78191036.Hotel-Information)

![One Bedroom Condo King with Ocean view | Living area](https://images.trvl-media.com/lodging/119000000/118950000/118940400/118940366/fd0f941b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![One Bedroom Condo King with Steam Shower | Living area](https://images.trvl-media.com/lodging/119000000/118950000/118940400/118940366/a9bb02b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![One Bedroom Condo King with Ocean view | Beach/ocean view](https://images.trvl-media.com/lodging/119000000/118950000/118940400/118940366/173765ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room dining](https://images.trvl-media.com/lodging/119000000/118950000/118940400/118940366/0ca01820.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Offshore Residences

[](https://www.expedia.ca/Montauk-Hotels-Offshore-Residences.h118940366.Hotel-Information)

Downtown Montauk

CA $655

CA $905 total

includes taxes & fees

Feb 22 - Feb 23

[](https://www.expedia.ca/Montauk-Hotels-Offshore-Residences.h118940366.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/90000000/89990000/89981800/89981758/7b5c5b88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/90000000/89990000/89981800/89981758/w1170h1164x0y1-82df79df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/90000000/89990000/89981800/89981758/w1170h1461x0y0-bc75bc71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/90000000/89990000/89981800/89981758/w1169h650x0y0-3f68a3a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Rams Head Inn

[](https://www.expedia.ca/Shelter-Island-Heights-Hotels-The-Rams-Head-Inn.h89981758.Hotel-Information)

Shelter Island Heights

7.6/10

Good

(18 reviews)

"Beautiful views and lovely service "

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

Lana

[](https://www.expedia.ca/Shelter-Island-Heights-Hotels-The-Rams-Head-Inn.h89981758.Hotel-Information)

![Private kitchen](https://images.trvl-media.com/lodging/110000000/109670000/109662700/109662697/1190496c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Flat-screen TV](https://images.trvl-media.com/lodging/110000000/109670000/109662700/109662697/934c8d81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room safe, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/110000000/109670000/109662700/109662697/253d38d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Flat-screen TV](https://images.trvl-media.com/lodging/110000000/109670000/109662700/109662697/ef1a1d3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Canoe Place Waterfront Residences

[](https://www.expedia.ca/Hampton-Bays-Hotels-Canoe-Place-Waterfront-Residences.h109662697.Hotel-Information)

Hampton Bays

10/10

Exceptional

(1 review)

[](https://www.expedia.ca/Hampton-Bays-Hotels-Canoe-Place-Waterfront-Residences.h109662697.Hotel-Information)

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## Explore similar 5-star hotels

Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Shelter Island Heights.

![Mill House Inn](https://images.trvl-media.com/lodging/3000000/2870000/2861900/2861838/e0e0def6_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Mill House Inn

31 North Main Street East Hampton NY

CA $342

CA $430 total

Feb 22 - Feb 23

includes taxes & fees

9/10 Wonderful! (80 reviews)

[](https://expedia.ca/East-Hampton-Hotels-Mill-House-Inn.h2861838.Hotel-Information)

![Casa Newmark Holiday home 7 BestStayz.1](https://images.trvl-media.com/lodging/33000000/32420000/32411100/32411044/23f4590c_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Casa Newmark Holiday home 7 BestStayz.1

112 Northwest Path Sagaponack NY

[Get rates](https://expedia.ca/Hotel-Search?startDate=07%2F03%2F2026&endDate=08%2F03%2F2026&selected=32411044&PinnedHotelID=32411044&HadPinnedHotel=true&regionId=183716)

[](https://expedia.ca/Sagaponack-Hotels-Casa-Newmark-Holiday-Home-7-BestStayz1.h32411044.Hotel-Information)

Still don't see what you're looking for?

[See all properties in Shelter Island Heights.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&regionId=183716&star=40)

You can also use these popular filters to refine your search.

[Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&regionId=183716&star=40&star=40&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&regionId=183716&star=40&star=40&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&regionId=183716&star=40&star=40&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&regionId=183716&star=40&star=40&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&regionId=183716&star=40&star=40&amenities=WATER_PARK)

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.

## Learn more about Shelter Island Heights

Victorian homes line the streets of this charming hamlet where you can rent bikes to explore the island's quiet beaches. Reserve a table at one of the waterfront restaurants for sunset views or take the short ferry to Greenport for more dining options.

[See all hotels in Shelter Island Heights](https://www.expedia.ca/Hotel-Search?startDate=2026-03-07&endDate=2026-03-08&adults=2&regionId=183716)

![View of Dering Harbor](https://images.trvl-media.com/place/157359/8df1734b-1204-4cc5-a5a0-67f90d8a76a3.jpg?impolicy=fcrop&w=650&h=652&p=1&q=high)

Photo by Brian V. Rowe

## Top Shelter Island Heights Hotel Reviews

![Gurney's Montauk Resort & Seawater Spa](https://images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/895004c9_y.jpg)

### Gurney's Montauk Resort & Seawater Spa

10/10 Excellent

"There were no iron in my room just the ironing board. Also called the front desk around 1am to get a ride back to our room from main property but there was no answer so my partner and I had to walk back to our room. Otherwise the stay was great. Loved the bath house. Also loved the versatility of the property restaurant. Room were nice and spacious with a breathtaking view."

[](https://expedia.ca/Montauk-Hotels-Gurneys-Montauk-Resort-Seawater-Spa.h7033726.Hotel-Information)

![Sound View Greenport](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4_y.jpg)

### Sound View Greenport

10/10 Excellent

"Amazing room and view from the room was perfect! "

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

## Find out more about Shelter Island Heights

If you’re looking for a spot with great rates, just-for-you amenities, and a world of luxurious little perks, the best 4 Stars hotels in Shelter Island Heights are calling your name. Known for providing first-rate service in amazing locations, each of the Shelter Island Heights 4 Stars hotels lets discerning travelers bask in an unforgettable experience.

Kick back in your spacious room. Relax in the lobby’s sumptuous surroundings. Start the day with delicious room service, and then use the complimentary body care items to freshen up before you head out for the day.

It’s all waiting for you at the top four star hotels in Shelter Island Heights. Plus, when you book with Expedia.ca, you might find a cheap deal on a 4 Stars hotel in Shelter Island Heights, New York, neighbourhoods near the most popular attractions, so you can see the sights and bask in the discounts all in one trip. Whether you’re planning a romantic retreat or simply want to experience everything the area has to offer, the top Shelter Island Heights hotels with 4 Stars provide everything you need to unwind in style.

## Frequently asked questions

### What are the best 4-star hotels in Shelter Island Heights?

### How much does it cost to stay in a 4-star hotel in Shelter Island Heights?

> - Search for the lowest price from CA $430

### What's the difference between 5-star and 4-star hotels in Shelter Island Heights?

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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)
- [Southold Hotels ](https://www.expedia.ca/Southold-Hotels.d183719.Travel-Guide-Hotels)
- [Motels in Southold ](https://www.expedia.ca/Southold-Motels.d183719-aaMotels.Travel-Guide-Accommodation)
- [Hotels near Sunset Beach ](https://www.expedia.ca/Sunset-Beach-Hotels.0-l553248626388141313-0.Travel-Guide-Filter-Hotels)
- [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 Shelter Island ](https://www.expedia.ca/Cheap-Flights-To-Shelter-Island.d157359.Travel-Guide-Flights)
- [Flights from Shelter Island ](https://www.expedia.ca/lp/flights/157359/flights-from-shelter-island)
- [Flights from Southold ](https://www.expedia.ca/lp/flights/183719/flights-from-southold)
- [Flights from East Marion ](https://www.expedia.ca/lp/flights/6069914/flights-from-east-marion)
- [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 Shelter Island ](https://www.expedia.ca/Shelter-Island.dx157359)

- [Car rental Greenport ](https://www.expedia.ca/Car-Rentals-In-Greenport.d110728.Car-Rental-Guide)
- [Car rental Shelter Island ](https://www.expedia.ca/Car-Rentals-In-Shelter-Island.d157359.Car-Rental-Guide)

- [Shelter Island Vacation Rentals ](https://www.expedia.ca/Shelter-Island-Vacation-Rentals.d157359.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 Shelter Island ](https://www.expedia.ca/Things-To-Do-In-Shelter-Island.d157359.Travel-Guide-Activities)

- [Book 4 Star Hotels in Shelter Island Heights on Expedia.com ](https://www.expedia.com/4Star-Shelter-Island-Heights-Hotels.s40-0-d183716.Travel-Guide-Filter-Hotels)