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Check prices for these dates

Next weekend
21 Feb - 23 Feb
In two weeks
28 Feb - 2 Mar
In one month
14 Mar - 16 Mar
In two months
11 Apr - 13 Apr

Compare 15 Resorts in Shelter Island with updated reviews, rates, and availability.

Water's Edge Resort & Spa
Exterior

Water's Edge Resort & Spa

3.5 star property
8.8 out of 10, Excellent, (1004)
"I love this property! I stayed for one night and there was a comedian and a lot of activity in the hotel which made for a great night! My only complaint is the bed! It was probably the least comfortable bed I have ever slept in a hotel. I had a horrible night sleep as the mattress was terrible! The room and amenities are all top notch! I am not a fan of the blue toilet water as a cleaner… but just my personal opinion. "
The price is AED 625
AED 782 total
includes taxes & fees
2 Mar - 3 Mar
Water's Edge Resort & Spa
Gurney's Montauk Resort & Seawater Spa
Room

Gurney's Montauk Resort & Seawater Spa

4.0 star property
8.2 out of 10, Very Good, (610)
"Beautiful views. Great staff and amenities."
The price is AED 1,377
AED 1,878 total
includes taxes & fees
10 Mar - 11 Mar
Gurney's Montauk Resort & Seawater Spa
Brand New Waterfront - Chic & Sophisticated Unit # 703
Terrace/patio

Brand New Waterfront - Chic & Sophisticated Unit # 703

10.0 out of 10, Exceptional, (5)
"the stay was good would have appreciated if there was coffee available at the property "
Brand New Waterfront - Chic & Sophisticated Unit # 703
Brand New Waterfront - Chic & Sophisticated Unit # 704
Living area

Brand New Waterfront - Chic & Sophisticated Unit # 704

Brand New Waterfront - Chic & Sophisticated Unit # 704
Ocean Colony Beach and Tennis Club
Terrace/patio

Ocean Colony Beach and Tennis Club

2.0 star property
Ocean Colony Beach and Tennis Club
Brand New Waterfront - Chic & Sophisticated
Living area

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
Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6
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
Brand New Waterfront - Chic & Sophisticated Unit # 702
Living area

Brand New Waterfront - Chic & Sophisticated Unit # 702

Brand New Waterfront - Chic & Sophisticated Unit # 702
Available July 21-28, 2023
Pool

Available July 21-28, 2023

8.8 out of 10, Excellent, (3)
"This rental was absolutely perfect. Room was exactly as described and very clean and well maintained. Very short walk to beach and pool. Water’s Edge staff was extremely courteous and attentive. The grounds are gorgeous and well maintained. The pool and beach combo was perfect for a family with kids. The owner of this rental was very easy to communicate with and responded quickly. We have zero complaints. We will absolutely be back again!"
Available July 21-28, 2023
Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6
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
Duryea's Sunset Cottages
Exterior

Duryea's Sunset Cottages

3.5 star property
Duryea's Sunset Cottages
Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 4
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
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
Water's Edge Resort & Spa (May 17, 2024 - May 24, 2024)
Pool

Water's Edge Resort & Spa (May 17, 2024 - May 24, 2024)

Water's Edge Resort & Spa (May 17, 2024 - May 24, 2024)
Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6
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
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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Other property types in Shelter Island

Montauk Manor
Exterior

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1111)
"Nice, pleasant, staff was warm and friendly "
The price is AED 481
AED 621 total
includes taxes & fees
18 Feb - 19 Feb
Montauk Manor
Montauk Oceanside Suites
Front of property

Montauk Oceanside Suites

3.0 star property
8.4 out of 10, Very Good, (361)
"I rented a room with a kitchen. And all it had was a fridge and microwave… otherwise I love it there"
The price is AED 412
AED 507 total
includes taxes & fees
27 Feb - 28 Feb
Montauk Oceanside Suites
Windward Shores Ocean Resort
Property grounds

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (271)
"Beautiful location, clean property, and nice staff. Just hard to turn in to the parking lot but not much that the hotel can do for that. The private beach is stunning. "
The price is AED 484
AED 632 total
includes taxes & fees
18 Feb - 19 Feb
Windward Shores Ocean Resort
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.

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: Water’s Edge Resort & Spa - Beach resort. 15.6 mi (25.1 km) from Shelter Island. Features 3 restaurants, a private beach, and a full-service spa. Highly rated for its great beach location. Gurney’s Montauk Resort & Seawater Spa - Beach resort. 18.4 mi (29.7 km) from Shelter Island. Has 2 restaurants, a private beach, and a full-service spa. Ocean Colony Beach and Tennis Club - Beach resort, 5-minute walk from The Hamptons Beaches. 15.9 mi (25.6 km) from Shelter Island. Enjoy the seasonal outdoor pool, garden, and free self parking. Brand New Waterfront - Chic & Sophisticated Unit # 703 - Situated just 10 minutes away 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 Unit # 704 - 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 Mashomack Preserve.
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.