Photo by tom owens

Search Resorts in Shelter Island

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
27 Jun - 29 Jun
In two weeks
4 Jul - 6 Jul
In one month
18 Jul - 20 Jul
In two months
15 Aug - 17 Aug

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, (635)
"Gurneys Inn was a beautiful place to stay. The staff extremely attentive and friendly!"
The price is SARĀ 2,478
SARĀ 3,382 total
includes taxes & fees
18 Jun - 19 Jun
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)
"It was a wonderful stay except for the weather! Very friendly staff."
The price is SARĀ 1,122
SARĀ 1,355 total
includes taxes & fees
18 Jun - 19 Jun
Water's Edge Resort & Spa
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
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 Unit # 702
Terrace/patio

Brand New Waterfront - Chic & Sophisticated Unit # 702

Brand New Waterfront - Chic & Sophisticated Unit # 702
Available July 21-28, 2023
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. Waterā€™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
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 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
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
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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: Gurneyā€™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. Waterā€™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 - Located just 10 minutes from The Hamptons Beaches. 20.8 mi (33.5 km) from Shelter Island. Enjoy the fitness center and garden. Duryeaā€™s Sunset Cottages - Only a 5-minute walk from The Hamptons Beaches. 19.9 mi (32.1 km) from Shelter Island. Access to a private beach, free self parking, and a hot tub.
What can I do in Shelter Island?
Grab your golf clubs for a game at Gardinerā€™s Bay Country Club, or bring the kids to Shelter Island Whaleā€™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 70Ā°F, while the coldest months are January and February with an average of 38Ā°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 youā€™d like to venture out around the area, you may want to rent a car for your trip.