Search Resorts in Shelter Island

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Check prices for these dates

Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 Feb

Our top choices for Shelter Island resorts

Exterior
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 star property
Westbrook Center
8.8 out of 10, Excellent, (1002)
"Yes! Ease of registration! The staff helped us with dinning suggestions, hotel programs and amenities!"
United States
Bruce
The price is AED 757
AED 934 total
includes taxes & fees
15 Dec - 16 Dec
Water's Edge Resort & Spa
Outdoor wedding area
Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4.0 star property
Montauk
8.2 out of 10, Very Good, (697)
"Beautiful view and accomodations. Enjoyed the bathhouse and hotel amenities"
United States
Alex
The price is AED 1,352
AED 1,845 total
includes taxes & fees
5 Jan - 6 January 2026
Gurney's Montauk Resort & Seawater Spa
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.
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Top Shelter Island Hotel Reviews

The Harbor Front Inn

The Harbor Front Inn

10/10 Excellent
"Yes"
Ray 1-night trip
Posted 2 days ago
The Harbor Front Inn

Frequently asked questions

What is Shelter Island like for a resort vacation?
Longing for a relaxing getaway? Treat yourself to the comforts and luxuries of a resort, where you can find everything you want for your trip from tasty food and drink options to activities and shopping. Browse the resort options in the area and discover the right one for you, whether you picture yourself sitting down to fine dining or hitting the golf course for an afternoon game.
What's a favorite resort in Shelter Island?
Here are our top-rated resorts around Shelter Island: Gurney's Montauk Resort & Seawater Spa - Beach resort. 18.4 mi (29.7 km) from Shelter Island. Features 2 restaurants, a private beach, and a full-service spa. Water's Edge Resort & Spa - Beach resort. 15.6 mi (25.1 km) from Shelter Island. Has 3 restaurants, a private beach, and a full-service spa. Highly rated for its great beach location. Brand New Waterfront - Chic & Sophisticated Unit # 702 - 20.8 mi (33.5 km) from Shelter Island. Enjoy the fitness center and garden. Duryea's Sunset Cottages - 19.9 mi (32.1 km) from Shelter Island. Amenities include a private beach, free self parking, and a hot tub. Brand New Waterfront - Chic & Sophisticated - 20.8 mi (33.5 km) from Shelter Island. Access to a fitness center and a garden.
What can I do in Shelter Island?
Grab your golf clubs for a game at Gardiner's Bay Country Club, or bring the kids to Shelter Island Whale's Tail for some family fun. For more to see in the area, you can spend time at Sunset Beach or Shelter Island Historical Society.
What's the weather like in Shelter Island?
The hottest months are usually August and July with an average temp of 70°F, while the coldest months are January and February with an average of 38°F. Average annual precipitation for Shelter Island is 57 inches.
What's the best way to get to and around Shelter Island?
Fly into East Hampton, NY (HTO), which is located 8.8 mi (14.2 km) away from the city center. You can also search for flights into Fishers Island, NY (FID-Elizabeth Field), which is 20.6 mi (33.1 km) away. If you'd like to venture out around the area, you may want to rent a car for your trip.