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Check prices for these dates

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25 Jul - 27 Jul
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1 Aug - 3 Aug
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15 Aug - 17 Aug
In two months
12 Sep - 14 Sep

Resorts in Shelter Island

Gurney's Montauk Resort & Seawater Spa
Outdoor wedding area

Gurney's Montauk Resort & Seawater Spa

4.0 star property
8.2 out of 10, Very Good, (647)
"Gurneys Inn was a beautiful place to stay. The staff extremely attentive and friendly!"
The price is AED 3,216
AED 4,389 total
includes taxes & fees
23 Jul - 24 Jul
Gurney's Montauk Resort & Seawater Spa
Water's Edge Resort & Spa
Exterior

Water's Edge Resort & Spa

3.5 star property
8.8 out of 10, Excellent, (1000)
"Grounds are beautiful. Good food and staff. One down side are the bed pillows- all were toooo big and puffy- so uncomfortable! "
The price is AED 1,098
AED 1,326 total
includes taxes & fees
22 Jul - 23 Jul
Water's Edge Resort & Spa
Brand New Waterfront - Chic & Sophisticated Unit # 703
Terrace/patio

Brand New Waterfront - Chic & Sophisticated Unit # 703

10.0 out of 10, Exceptional, (5)
"Very comfortable space, great location, close to many restaurants and beaches"
Brand New Waterfront - Chic & Sophisticated Unit # 703
Brand New Waterfront - Chic & Sophisticated
Terrace/patio

Brand New Waterfront - Chic & Sophisticated

10.0 out of 10, Exceptional, (1)
"The Host, Steve was very responsive and helpful. Accommodations are great for a couple, a young family, a small family, or even just some friends! Very spacious and we loved the en-suite bathrooms in the bedrooms. Kitchen was fully equipped with lots of tools. Ample pantry space to store your own goods! Laundry machines were great. Very spacious and great for our family getaway!"
Brand New Waterfront - Chic & Sophisticated
Brand New Waterfront - Chic & Sophisticated Unit # 704
Terrace/patio

Brand New Waterfront - Chic & Sophisticated Unit # 704

Brand New Waterfront - Chic & Sophisticated Unit # 704
Duryea's Sunset Cottages
Luxury Cottage, Bay View | 1 bedroom, Frette Italian sheets, premium bedding, down comforters

Duryea's Sunset Cottages

2.5 star property
Duryea's Sunset Cottages
Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6
Indoor pool, a heated pool

Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6

Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6
Water's Edge Resort & Spa May 23, 2025 - May 30, 2025
Pool

Water's Edge Resort & Spa May 23, 2025 - May 30, 2025

Water's Edge Resort & Spa May 23, 2025 - May 30, 2025
Ocean Colony Beach and Tennis Club
Cozy Pad 2BR Beachside Home | TennisPoolFreePKG Unit 721 | Terrace/patio

Ocean Colony Beach and Tennis Club

2.0 star property
Ocean Colony Beach and Tennis Club
Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6
Indoor pool, outdoor pool

Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6

8.0 out of 10, Very Good, (1)
"Comfortable space for a small family. We liked the flexibility of having a small beach on property and our own kitchen. The owner was easy to contact too."
Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6
Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 4
Indoor pool, a heated pool

Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 4

Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 4
Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6
Indoor pool, a heated pool

Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6

Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6
Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6
Indoor pool, outdoor pool

Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6

10.0 out of 10, Exceptional, (1)
"Had a great stay for a long weekend getaway! The unit was in great shape, and we really enjoyed ourselves!"
Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6
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

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

10/10 Excellent
"I always enjoy stopping at the Saybrook Inn and Spa. The front desk gentleman were very nice and welcomed me back. We arrived almost at restaurant closing time and our server was accommodating and kind. The hotel is pet friendly and the breakfast wait staff were great. Look forward to our next visit."
Linda 1-night trip
Posted 1 day ago
Saybrook Point Resort & Marina

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 # 703 - Located just 10 minutes from The Hamptons Beaches. 20.8 mi (33.5 km) from Shelter Island. Enjoy the fitness center and garden. Brand New Waterfront - Chic & Sophisticated Unit # 702 - Located just 10 minutes from The Hamptons Beaches. 20.8 mi (33.5 km) from Shelter Island. Amenities include a fitness center and a garden. Brand New Waterfront - Chic & Sophisticated - Situated just 10 minutes away from The Hamptons Beaches. 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 Crescent Beach.
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.