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Go beyond your typical stay in Shelter Island

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Our top choices for Shelter Island hotels

1. Sound View Greenport
Sound View GreenportGreenport
8.4 out of 10, Very good, (768 reviews)
The price is CA $212
CA $283 total
includes taxes & fees
Dec 14 - Dec 15

2. The Chequit
The ChequitThe Heights
9.0 out of 10, Wonderful, (78 reviews)
The price is CA $244
CA $279 total
includes taxes & fees
Nov 19 - Nov 20

3. The Pridwin Hotel
The Pridwin HotelShelter Island Heights
9.6 out of 10, Exceptional, (128 reviews)

5. The Harbor Front Inn
The Harbor Front InnGreenport
9.0 out of 10, Wonderful, (676 reviews)
The price is CA $181
CA $248 total
includes taxes & fees
Dec 13 - Dec 14

6. The Shoals Suites and Slips
The Shoals Suites and SlipsSouthold
9.4 out of 10, Exceptional, (351 reviews)
The price is CA $265
CA $338 total
includes taxes & fees
Nov 17 - Nov 18

7. Silver Sands Motel & Beach Bungalows
Silver Sands Motel & Beach BungalowsGreenport
10.0 out of 10, Exceptional, (193 reviews)
The price is CA $295
CA $337 total
includes taxes & fees
Dec 13 - Dec 14

8. Cliffside Resort Condominiums
Cliffside Resort CondominiumsGreenport
9.0 out of 10, Wonderful, (300 reviews)
The price is CA $274
CA $471 total
includes taxes & fees
Nov 26 - Nov 27

9. The Menhaden
The MenhadenGreenport
9.6 out of 10, Exceptional, (197 reviews)
The price is CA $363
CA $479 total
includes taxes & fees
Dec 13 - Dec 14

10. Montauk Manor
Montauk ManorMontauk
9.2 out of 10, Wonderful, (1,425 reviews)
The price is CA $198
CA $254 total
includes taxes & fees
Dec 1 - Dec 2

11. West Neck Guesthouse
West Neck GuesthouseShelter Island Heights
8.2 out of 10, Very good, (46 reviews)

12. Shelter Island House
Shelter Island HouseShelter Island Heights
8.4 out of 10, Very good, (66 reviews)

13. Gurney's Montauk Resort & Seawater Spa
Gurney's Montauk Resort & Seawater SpaMontauk
8.2 out of 10, Very good, (881 reviews)
The price is CA $509
CA $698 total
includes taxes & fees
Nov 29 - Nov 30

14. Hilton Mystic
Hilton MysticMystic
8.8 out of 10, Excellent, (1,246 reviews)
The price is CA $151
CA $174 total
includes taxes & fees
Nov 22 - Nov 23

15. American Beech Hotel
American Beech HotelGreenport
9.0 out of 10, Wonderful, (208 reviews)
The price is CA $341
CA $446 total
includes taxes & fees
Nov 15 - Nov 16

16. Oyster Estate
Oyster EstateGreenport
9.2 out of 10, Wonderful, (302 reviews)
The price is CA $257
CA $324 total
includes taxes & fees
Dec 13 - Dec 14

17. Faraway Sag Harbor
Faraway Sag HarborSag Harbor
9.0 out of 10, Wonderful, (322 reviews)
The price is CA $416
CA $523 total
includes taxes & fees
Dec 15 - Dec 16

19. Sag Harbor Inn
Sag Harbor InnSag Harbor
9.4 out of 10, Exceptional, (689 reviews)
The price is CA $312
CA $357 total
includes taxes & fees
Nov 17 - Nov 18

20. Spark by Hilton Mystic Groton
Spark by Hilton Mystic GrotonMystic
8.2 out of 10, Very good, (2,010 reviews)
The price is CA $128
CA $147 total
includes taxes & fees
Nov 22 - Nov 23
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.
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
Learn more about Shelter Island

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.

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.

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.

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.

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.
Stay near popular Shelter Island attractions
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.






















































































