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12 Sep - 14 Sep
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Resorts in Shelter Island

Our top choices for Shelter Island resorts

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, (663)
"It was clean and staff is very nice "
The price is AED 2,119
AED 2,892 total
includes taxes & fees
5 Oct - 6 Oct
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, (1010)
"It was a great time we really enjoyed our stay!!"
The price is AED 790
AED 972 total
includes taxes & fees
15 Sep - 16 Sep
Water's Edge Resort & Spa
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
10.0 out of 10, Exceptional, (2)
"We were looking for a getaway from the our daily lives and man we found the perfect spot! Hands down one of the best customer service experiences I’ve ever had. Jessica, the property manager, was incredible, very kind, welcoming, and always available. The housekeeping team was just as amazing, keeping everything spotless and making us feel right at home. Breakfast every morning was a perfect touch, and the same thoughtful service carried over to their restaurant too. The cottage was peaceful,...
Duryea's Sunset Cottages
Brand New Waterfront - Chic & Sophisticated Unit # 702
Terrace/patio

Brand New Waterfront - Chic & Sophisticated Unit # 702

Brand New Waterfront - Chic & Sophisticated Unit # 702
Brand New Waterfront - Chic & Sophisticated
Terrace/patio

Brand New Waterfront - Chic & Sophisticated

7.0 out of 10, Good, (2)
"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 # 703
Terrace/patio

Brand New Waterfront - Chic & Sophisticated Unit # 703

10.0 out of 10, Exceptional, (6)
"Very comfortable space, great location, close to many restaurants and beaches"
Brand New Waterfront - Chic & Sophisticated Unit # 703
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
Brand New Waterfront - Chic & Sophisticated Unit # 704
Terrace/patio

Brand New Waterfront - Chic & Sophisticated Unit # 704

Brand New Waterfront - Chic & Sophisticated Unit # 704
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

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
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 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, 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 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.
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Top Shelter Island Hotel Reviews

The Harbor Front Inn

The Harbor Front Inn

10/10 Excellent
"Great location ,beautiful hotel,nice staff"
ROBERT 1-night trip
Posted 10 days ago
The Harbor Front Inn
Sound View Greenport

Sound View Greenport

10/10 Excellent
"Our luxury 2 bedroom suite was very nice, clean, and spacious. We had a huge balcony with a view of the Long Island sound"
christine 2-night trip
Posted 2 weeks ago
Sound View Greenport

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. Duryea's Sunset Cottages - Situated just a 5-minute walk from The Hamptons Beaches. 19.9 mi (32.1 km) from Shelter Island. Enjoy the private beach, free self parking, and hot tub. 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.
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.