Title: The 10 Best Hotels Near Shelter Island Whale's Tail, Shelter Island from CA $235 | 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 Whale's Tail Car Rentals](https://expedia.ca/Car-Rentals-In-Shelter-Island-Whales-Tail.d553248621554204762.Car-Rental-Guide)[Shelter Island Whale's Tail Vacations](https://expedia.ca/Shelter-Island-Whales-Tail-Shelter-Island.d553248621554204762.Vacation-Attraction)

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# Find hotels near Shelter Island Whale's Tail, Shelter Island from CA $235

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## Check prices for these dates

Tonight

[Dec 4 - Dec 5](https://www.expedia.ca/Hotel-Search?regionId=553248621554204762&startDate=2025-12-04&endDate=2025-12-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Dec 5 - Dec 6](https://www.expedia.ca/Hotel-Search?regionId=553248621554204762&startDate=2025-12-05&endDate=2025-12-06&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=553248621554204762&startDate=2025-12-05&endDate=2025-12-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=553248621554204762&startDate=2025-12-12&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Recommended

Price (low to high)

Distance

Star rating

## Top Hotels Close to Shelter Island Whale's Tail

![View from property](https://images.trvl-media.com/lodging/13000000/12620000/12611000/12610909/51be5ca3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/13000000/12620000/12611000/12610909/fdb9f048.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/13000000/12620000/12611000/12610909/d7311f73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lake](https://images.trvl-media.com/lodging/13000000/12620000/12611000/12610909/8cc5044d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### House on Chase Creek

1.9 km from Shelter Island Whale's Tail

9.4/10

Exceptional

(79)

" This was my husband and my first time visiting Shelter Island and I feel lucky that my stay was at the House of ChaseCreek. Bill was excellent in helping us navigate our stay on the Island which made for an enjoyable experience. The house was charming , very clean , and had easy access to the town restaurant s, and Ferry. Highly recommend ! "

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

Maureen

CA $258

CA $295 total

includes taxes & fees

Dec 8 - Dec 9

[](https://www.expedia.ca/Shelter-Island-Heights-Hotels-House-On-Chase-Creek.h12610909.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 | View from room](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/8f5285b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Waterfront Beach Shack Studio](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/65a8ebbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach Shack w/ Sleeping Alcove](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/b99eb106.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Silver Sands Motel & Beach Bungalows

4.2 km from Shelter Island Whale's Tail

9.8/10

Exceptional

(139)

"amazing stay, very quaint and relaxing "

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

rebecca

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

![Garden Suite, Wheelchair Accessible, Ground Floor, 2 Queen Beds, Non-Smoking](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/20957ef0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/dc9e5678.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/bfb5cc4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Zey Hotel

3.9 km from Shelter Island Whale's Tail

9.2/10

Wonderful

(290)

"Loved this place. Lots of places to relax and play games. Super-friendly staff. Can't wait to go back b"

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

Susie

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

![Garden Suite King](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/968755d8.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)

![Boardwalk Suite | Private kitchen](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/1898cf3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/22f2b7c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Shoals Suites and Slips

6 km from Shelter Island Whale's Tail

9.6/10

Exceptional

(224)

"Great quick stay"

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

Jasmine T

CA $238

CA $272 total

includes taxes & fees

Dec 10 - Dec 11

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

![One Bedroom Harbor View Terrace Suite | View from room](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/46cd22ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property entrance](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/a8d80546.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Balcony view](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/64ea9871.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby lounge](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/4e8534b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Harbor Front Inn

3.8 km from Shelter Island Whale's Tail

8.8/10

Excellent

(540)

"Awesome stay!!! Great Location "

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

Bryan

CA $146

CA $235 total

includes taxes & fees

Dec 29 - Dec 30

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

![Property entrance](https://images.trvl-media.com/lodging/36000000/35230000/35229400/35229370/bc0d37bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast served](https://images.trvl-media.com/lodging/36000000/35230000/35229400/35229370/5b2ed019.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)

![1 bedroom, premium bedding, down comforters, memory foam beds](https://images.trvl-media.com/lodging/36000000/35230000/35229400/35229370/20266156.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Menhaden

3.8 km from Shelter Island Whale's Tail

9.6/10

Exceptional

(171)

"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 $263

CA $356 total

includes taxes & fees

Jan 4 - Jan 5, 2026

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

![Exterior](https://images.trvl-media.com/lodging/12000000/11960000/11951200/11951124/0caf92d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/12000000/11960000/11951200/11951124/52855a41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 King Bed (#1)](https://images.trvl-media.com/lodging/12000000/11960000/11951200/11951124/339409ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Suite | Living area](https://images.trvl-media.com/lodging/12000000/11960000/11951200/11951124/767aee45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### American Beech Hotel

3.8 km from Shelter Island Whale's Tail

8.8/10

Excellent

(195)

"The property was clean beautiful and pleasant. Loved the trendy decor."

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

Jennifer

CA $278

CA $373 total

includes taxes & fees

Dec 8 - Dec 9

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

![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4.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, 2 Queen Beds](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/f76cf168.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/4c9856c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sound View Greenport

5.9 km from Shelter Island Whale's Tail

8.6/10

Excellent

(596)

"Staff was amazing , room clean view phenomenal "

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

Denise

CA $211

CA $309 total

includes taxes & fees

Dec 9 - Dec 10

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

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

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

![Property entrance](https://images.trvl-media.com/lodging/27000000/26500000/26497900/26497858/db237a24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sag Harbor Inn

8.8 km from Shelter Island Whale's Tail

9.4/10

Exceptional

(570)

"We had lovely stay, the staff was knowledgeable, efficient, and friendly. Will visit again! "

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

Lori

CA $270

CA $308 total

includes taxes & fees

Dec 7 - Dec 8

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

![Interior entrance](https://images.trvl-media.com/lodging/97000000/96720000/96718100/96718085/a9ca389a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior detail](https://images.trvl-media.com/lodging/97000000/96720000/96718100/96718085/dd468523.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/97000000/96720000/96718100/96718085/63390424.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool](https://images.trvl-media.com/lodging/97000000/96720000/96718100/96718085/59bbc572.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vine & Sand

9.7 km from Shelter Island Whale's Tail

9.6/10

Exceptional

(13)

"This B&B, and its hosts, were simply amazing. I cannot recommend this place enough."

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

Sandra

[](https://www.expedia.ca/Southold-Hotels-Vine-Sand.h96718085.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)

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

![Master Guest Room](https://images.trvl-media.com/lodging/32000000/31010000/31007600/31007589/90421aa1.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)

### East Hampton Art House Bed & Breakfast

14.7 km from Shelter Island Whale's Tail

9.6/10

Exceptional

(65)

"Roz and Michael built a beautiful paradise that they enjoy sharing with you. Everything is amazing. "

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

Dan

CA $548

CA $627 total

includes taxes & fees

Dec 8 - Dec 9

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

![Exterior](https://images.trvl-media.com/lodging/82000000/81150000/81143200/81143153/d64f35e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property entrance](https://images.trvl-media.com/lodging/82000000/81150000/81143200/81143153/ce84672e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/82000000/81150000/81143200/81143153/9a89f493.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/82000000/81150000/81143200/81143153/d13a2c2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Sagaponack

15.8 km from Shelter Island Whale's Tail

8.8/10

Excellent

(211)

"Clean & amenities, staff friendly Thank you "

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

Archil

CA $195

CA $279 total

includes taxes & fees

Dec 15 - Dec 16

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

![Outdoor wedding area](https://images.trvl-media.com/lodging/10000000/9380000/9371700/9371613/c3d577bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 2 Bedrooms (No Pets)](https://images.trvl-media.com/lodging/10000000/9380000/9371700/9371613/79b4f744.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/10000000/9380000/9371700/9371613/6e92e51d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/10000000/9380000/9371700/9371613/bb9abbf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bridgehampton Inn

15.9 km from Shelter Island Whale's Tail

9.4/10

Exceptional

(218)

"Great place!!!"

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

Leslie

CA $417

CA $477 total

includes taxes & fees

Dec 8 - Dec 9

[](https://www.expedia.ca/Bridgehampton-Hotels-Bridgehampton-Inn.h9371613.Hotel-Information)

![Garden](https://images.trvl-media.com/lodging/2000000/1090000/1085700/1085655/67db121e.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/2000000/1090000/1085700/1085655/3e8af6f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room 4, King Bed](https://images.trvl-media.com/lodging/2000000/1090000/1085700/1085655/bf954008.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The 1770 House Restaurant & Inn

17.7 km from Shelter Island Whale's Tail

9.8/10

Exceptional

(160)

"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 $370

CA $506 total

includes taxes & fees

Dec 8 - Dec 9

[](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)

![Premium bedding, minibar, in-room safe, desk](https://images.trvl-media.com/lodging/6000000/5590000/5581400/5581380/3f4839f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/6000000/5590000/5581400/5581380/e9d81899.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)

### Topping Rose House

15.6 km from Shelter Island Whale's Tail

9.2/10

Wonderful

(136)

"Great rooms, staff and food"

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

Alexandra

CA $725

CA $834 total

includes taxes & fees

Dec 8 - Dec 9

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

![Front of property - evening/night](https://images.trvl-media.com/lodging/3000000/2870000/2861900/2861838/e0e0def6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Graybarn Cottage | Living area](https://images.trvl-media.com/lodging/3000000/2870000/2861900/2861838/1fbed560.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Graybarn Cottage | Room amenity](https://images.trvl-media.com/lodging/3000000/2870000/2861900/2861838/1d639007.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/3000000/2870000/2861900/2861838/f6e6bd4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Mill House Inn

17.4 km from Shelter Island Whale's Tail

9.0/10

Wonderful

(73)

"We stayed at the Inn for our anniversary last weekend. We are devotees of bed and breakfast hotels and loved this one. We arrived to find a huge, and I mean, huge, bouquet of the most beautiful white roses waiting for us in the suite that they upgraded us to. Totally unexpected. These folks could not do enough for us. Breakfast was extremely nice, cooked to order with quality ingredients. Bed was extremely warm and comfortable. The management, the staff, can't say anything negative about...

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

margaret

CA $419

CA $526 total

includes taxes & fees

Dec 7 - Dec 8

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

![Garden](https://images.trvl-media.com/lodging/36000000/35380000/35373800/35373712/98e9a1b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free continental breakfast on weekends](https://images.trvl-media.com/lodging/36000000/35380000/35373800/35373712/062f5fd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 1 King Bed](https://images.trvl-media.com/lodging/36000000/35380000/35373800/35373712/398ec458.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/36000000/35380000/35373800/35373712/553f589d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Huntting Inn

17.7 km from Shelter Island Whale's Tail

9.0/10

Wonderful

(104)

"Staff and management was very welcoming!"

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

Sanailer

CA $534

CA $624 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/East-Hampton-Hotels-The-Huntting-Inn.h35373712.Hotel-Information)

![Beach nearby, white sand, sun loungers, beach umbrellas](https://images.trvl-media.com/lodging/11000000/10550000/10547800/10547745/b8adcc4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/11000000/10550000/10547800/10547745/1f4433ce.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/c6fa26de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Roundtree, Amagansett

19.5 km from Shelter Island Whale's Tail

10/10

Exceptional

(91)

"Located right in the center of town, the grounds on this property are wonderful with clean and comfortable suites. The staff are engaging and sweet. And the late night cookies are a sweet touch."

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

adam

CA $830

CA $996 total

includes taxes & fees

Jan 1 - Jan 2, 2026

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

![Exterior](https://images.trvl-media.com/lodging/24000000/23260000/23252100/23252049/acd2c1de.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/c353f8fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/24000000/23260000/23252100/23252049/d697dbfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, in-room safe, iron/ironing board, bed sheets](https://images.trvl-media.com/lodging/24000000/23260000/23252100/23252049/7c3abc76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Journey East Hampton

18.8 km from Shelter Island Whale's Tail

9.0/10

Wonderful

(159)

"We were able to access many beaches with the beach pass that came with the stay. That was the main reason we wanted to stay there. The rooms were very nice, spacious and comfortable. "

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

Sarah

CA $259

CA $325 total

includes taxes & fees

Dec 9 - Dec 10

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

![Garden](https://images.trvl-media.com/lodging/10000000/9660000/9652100/9652095/32700dd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Georgia Pond Junior Suite](https://images.trvl-media.com/lodging/10000000/9660000/9652100/9652095/386602b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Georgia Pond Junior Suite](https://images.trvl-media.com/lodging/10000000/9660000/9652100/9652095/e9e14566.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property - evening/night](https://images.trvl-media.com/lodging/10000000/9660000/9652100/9652095/5021abf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Maidstone

17.8 km from Shelter Island Whale's Tail

8.0/10

Very good

(150)

"We had a wonderful stay "

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

Sabrina

CA $363

CA $415 total

includes taxes & fees

Jan 2 - Jan 3, 2026

[](https://www.expedia.ca/East-Hampton-Hotels-The-Maidstone.h9652095.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=2025-12-18&endDate=2025-12-19&regionId=553248621554204762&adults=2&sort=RECOMMENDED&openPlayBack=true)

## Top Shelter Island Whale's Tail Hotel Reviews

![The Menhaden](https://images.trvl-media.com/lodging/36000000/35230000/35229400/35229370/bc0d37bf_y.jpg)

### The Menhaden

10/10 Excellent

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

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

![Work and Play Special!  Extended Stay Discount ](https://images.trvl-media.com/lodging/40000000/39940000/39934500/39934446/7033cd48_y.jpg)

### Work and Play Special! Extended Stay Discount 

10/10 Excellent

"This place is a perfect oasis in an already special environment. The host was wonderful and thoughtful. The cottage was magical and had everything to offer that one could want. "

[](https://expedia.ca/Shelter-Island-Hotels-Work-And-Play-Special-Extended-Stay-Discount-At-A-Hideaway-With-Stellar-Wifi.h39934446.Hotel-Information)

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

### Sound View Greenport

10/10 Excellent

"Great room with amazing views! Staff was fantastic and the food was great too"

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

![The Harbor Front Inn](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/46cd22ca_y.jpg)

### The Harbor Front Inn

10/10 Excellent

"Always love staying there when in Greenport. Clean. Central. Quality continental breakfast."

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

![American Beech Hotel](https://images.trvl-media.com/lodging/12000000/11960000/11951200/11951124/0caf92d6_y.jpg)

### American Beech Hotel

10/10 Excellent

"Outstanding on all levels.. Hospitality and food top notch."

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

![Zey Hotel](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/f2951978_y.jpg)

### Zey Hotel

10/10 Excellent

"Not applicable "

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

![Silver Sands Motel & Beach Bungalows](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/52eefc00_y.jpg)

### Silver Sands Motel & Beach Bungalows

10/10 Excellent

"Just a perfect little get away! The facility was perfectly quaint yet trendy, the staff was friendly, and it was so cozy and close to all the local wineries! 10/10 recommend and I will most definitely be back! "

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

![House on Chase Creek](https://images.trvl-media.com/lodging/13000000/12620000/12611000/12610909/51be5ca3_y.jpg)

### House on Chase Creek

10/10 Excellent

"The House on Chase Creek is absolutely amazing! My husband and I are celebrating our 20th anniversary and I’ve been telling him about Shelter Island literally for almost 40 years. Well we finally made it and the trip, the home, the welcoming of my dog, was all so just so welcoming and nice. Bill, the proprietor, took great care to answer any questions and tell us about the Island. Then we enter the most immaculate room, as clean as the ritz! I mean it…I broke a glass by my nightstand and had to move the stand to clean up the glass; when I say not one speck of dust, not one fuzz bunny, so clean you could eat off the floor, even under the bed!! We enjoyed our stay so much we extended our trip and Bill, was extremely helpful, and welcomed us to stay longer! We can’t wait to go back, and we are going to try and make it an annual event. Thank you Bill for all your kindness and see you soon!!! MA and Erich Schmalhorst. PS. The bed AMAZING, sleep so peaceful, I can’t express how wonderful this place is to stay in. I almost want to erase this review because I don’t want to let the “cat out of the bag”!"

[](https://expedia.ca/Shelter-Island-Heights-Hotels-House-On-Chase-Creek.h12610909.Hotel-Information)

![Harbor Knoll Bed & Breakfast](https://images.trvl-media.com/lodging/23000000/22810000/22804900/22804880/d47a17b9_y.jpg)

### Harbor Knoll Bed & Breakfast

10/10 Excellent

"fall season, pool not opened, been to Greenport before, weekends are best now, Halloween parade, plenty of small shops to peruse, bt check days and hours because of season"

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

## Hotels near other Shelter Island Whale's Tail attractions

### 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)

### Sylvester Manor

You can find out about the history of Shelter Island Heights when you stop by Sylvester Manor. Stroll along the beaches or discover the area's sunsets. 

[See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=6282169)

### 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)

### 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)

### 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)

### 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 Country Club

Enjoy a round of golf in Shelter Island Heights at Shelter Island Country Club. Stroll along the beaches or discover the area's sunsets. 

[See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=6282167)

## Frequently asked questions

### What's the area like around Shelter Island Whale's Tail?

### Where is the best place to stay near Shelter Island Whale's Tail?

### How many hotels are there near Shelter Island Whale's Tail?

### If I need to cancel the hotel reservation for my stay near Shelter Island Whale's Tail, will I receive a refund?

### What can I see and do near Shelter Island Whale's Tail?

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- [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 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)
- [Shelter Island Heights Vacations ](https://www.expedia.ca/Shelter-Island-Heights.d183716.Destination-Travel-Guides)
- [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 Heights ](https://www.expedia.ca/Things-To-Do-In-Shelter-Island-Heights.d183716.Travel-Guide-Activities)
- [Things to do in Shelter Island ](https://www.expedia.ca/Things-To-Do-In-Shelter-Island.d157359.Travel-Guide-Activities)