Best Resorts in Shelter Island

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Compare 9 Resorts in Shelter Island with updated reviews, rates, and availability.

Outdoor wedding area
Gurney's Montauk Resort & Seawater Spa
4.0 star property
8.2 out of 10, Very Good, (565)
"Amazing beds "
The price is $519
$708 total
includes taxes & fees
May 19 - May 20
Gurney's Montauk Resort & Seawater Spa
Exterior
Water's Edge Resort & Spa
3.5 star property
8.6 out of 10, Excellent, (1000)
"Hot tub area and sauna could use some updating, the pillows in the room were extremely uncomfortable. Everything else was good. "
The price is $237
$285 total
includes taxes & fees
May 22 - May 23
Water's Edge Resort & Spa
Exterior
Brand New Waterfront - Chic & Sophisticated Unit # 703
Brand New Waterfront - Chic & Sophisticated Unit # 703
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Exterior
Brand New Waterfront - Chic & Sophisticated
10.0 out of 10, Exceptional, (1)
"This condo was perfect for our Labor Day vacation. Great location. Easy access to beaches and restaurants. Clean and perfect size for our family of 4. We will certainly return. Steve the host was extremely responsive and answered all my questions."
Brand New Waterfront - Chic & Sophisticated
Exterior
Brand New Waterfront - Chic & Sophisticated Unit # 702
Brand New Waterfront - Chic & Sophisticated Unit # 702
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
Pool | Indoor pool, a heated 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
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
Exterior
Brand New Waterfront - Chic & Sophisticated
Brand New Waterfront - Chic & Sophisticated
Exterior
Brand New Waterfront - Chic & Sophisticated Unit # 704
Brand New Waterfront - Chic & Sophisticated Unit # 704
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
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
Pool | 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
Pool
Water's Edge Resort & Spa (May 17, 2024 - May 24, 2024)
Water's Edge Resort & Spa (May 17, 2024 - May 24, 2024)
Don't see what you're looking for?
See all available properties in Shelter Island
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.

Other property types in Shelter Island

Front of property - evening/night
Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1020)
"Best affordable hotel in Montauk"
The price is $168
$211 total
includes taxes & fees
May 20 - May 21
Montauk Manor
Apartment | Private kitchen | Fridge, microwave, stovetop
Montauk Oceanside Suites
3.0 star property
8.4 out of 10, Very Good, (295)
"We enjoyed our stay!"
The price is $156
$188 total
includes taxes & fees
May 22 - May 23
Montauk Oceanside Suites
On the beach, white sand
The Surf Club
3.5 star property
8.6 out of 10, Excellent, (219)
"An amazing stay with our girls!!! Can’t wait to go back!"
The price is $224
$310 total
includes taxes & fees
Jun 9 - Jun 10
The Surf Club
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.

Shelter Island Resorts information

Number of reviews
1,570
Accommodation
9 Resorts
Lowest Price
$237
Highest Price
$519

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.
What can I do in Shelter Island?
Check out the interesting exhibits at Havens House, or get some time by the water at Sunset Beach. For more to see in the area, you can spend time at Crescent Beach or Gardiner’s Bay Country Club.
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.

Recent reviews of Shelter Island hotels
Expedia verified reviews

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

5/5 Excellent
Nice hotel
"This is a no-frills hotel. However we had a mini fridge, microwave and coffee maker in our room. VERY spacious. Staff were friendly and at the front desk when we needed them to be there. A lady came to our door once to see if we needed fresh towels (we were there for 6 days). We will stay here on a return visit. Thanks Pier Blue staff"
A verified traveler stayed at Pier Blue Inn Old Saybrook - Essex
Posted 22 hours ago
Pier Blue Inn Old Saybrook - Essex