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10 Best Hotels in Shelter Island

Shelter Island Waterfront House With Dock And Private Beach
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0.69 km from city centre
5/5Exceptional! (13 reviews)
Great stay

"Perfect location and great house. Has everything you need for your stay. 1 minute walk to the beach for swimming. Nice deck to enjoy coffee in morning and drinks in evening"…"

Reviewed on 20 Aug. 2019

Shelter Island Waterfront House With Dock And Private Beach
New Listing: Technicolor Paradise, Architectural Masterpiece Amidst Woodlands & Beaches, and Heated Pool
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2.21 km from city centre
4.4/5Excellent! (5 reviews)

"Overpriced. Beds good. Uncomfortable and not well equipped."…"

Reviewed on 24 Sep. 2019

New Listing: Technicolor Paradise, Architectural Masterpiece Amidst Woodlands & Beaches, and Heated Pool
New Listing: Renovated & Modern, Waterviews, Walk to Beach, Heated Pool/hot Tub

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Spacious 4 bedroom beach home! Perfect retreat/grand piano, pond, deck, grounds.
NEW Listing: Farmhouse Renovated w/ Convenience + Comfort, Stylish and Charming Living
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2.16 km from city centre
5/5Exceptional! (1 review)
Beautifully designed and plenty of amenities

"This home exceeded our expectations in every way. The house is meticulously designed and at the same time feels warm and homey - almost like staying at an Friends’ house that is an interior designer by trade. The kitchen/dining room was perfect for group dinners - had everything you could want and ..."…"

Reviewed on 30 Aug. 2019

NEW Listing: Farmhouse Renovated w/ Convenience + Comfort, Stylish and Charming Living
Private Hamptons Cottage
94 S Ferry Rd, Shelter Island, NY
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1.08 km from city centre
5/5Exceptional! (5 reviews)
Paradise

"Fantastic!"…"

Reviewed on 9 Sep. 2019

Private Hamptons Cottage
Brand New House in Beach Community on Shelter Island, NY
Gurney’s Star Island Resort & Marina
3.5 out of 5
32 Star Island Rd, Montauk, NY
The price is AU$779 per night
31.95 km from city centre
4.1/5Very Good! (720 reviews)

"We had a great stay. Very clean and the renovations from the Old Yacht club were well done. Only complaint would be the food at the pool club..each time we had breakfast it felt like we were waisting money but what can you do during a pandemic. The new Showfish was great."…"

Reviewed on 13 Jul. 2020

Gurney’s Star Island Resort & Marina
Montauk Manor
3.5 out of 5
236 Edgemere St., Montauk, NY
The price is AU$303 per night
30.61 km from city centre
4.5/5Wonderful! (279 reviews)

"Perfect place for a family getaway. Staff was friendly and the room was very clean. The complimentary shuttle service is a definite plus. Highly recommend the property."…"

Reviewed on 31 Jul. 2020

Montauk Manor
Water's Edge Resort & Spa
3.5 out of 5
1525 Boston Post Road, Westbrook, CT
The price is AU$337 per night
26.82 km from city centre
4.3/5Excellent! (453 reviews)

"Beautiful location and resort. Great location right on the water. Enjoyed our stay with our family. Used the beach loungers and ate at the out door dining. Everything was great."…"

Reviewed on 20 Jul. 2020

Water's Edge Resort & Spa
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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.

Visiting Shelter Island

Visitors can enjoy all that Shelter Island has to offer including the golf courses, opera houses, and entertainment choices. In Shelter Island, there are 2 hotels and other accommodations to choose from. The closest major airport is in East Hampton, NY (HTO) 13.2 from the city center. The next closest is in Fishers Island, NY (FID-Elizabeth Field) 31.3 away.

Sightseeing and Staying in Shelter Island

The city's natural beauty is on display at Mashomack Preserve, Menhadden Lane Beach, and Wades Beach. A couple of additional sights to add to your agenda are Havens House and Shelter Island Whale's Tail.

As you plan your vacation to Shelter Island, the perfect accommodation may not be centrally located but you'll find 121 hotels and lodging options locally. Here are a few places to stay in the area:

  • Waterfront Home on Beautiful Shelter Island W/large Deep Water Dock is 2.2 mi from central Shelter Island. Guests who stay at this 4-star resort in Montauk can enjoy access to a full-service spa and a private beach, along with free WiFi. It's a favorite with Expedia travelers for its bar and clean, comfortable rooms.
  • Gurney's Montauk Resort & Seawater Spa is located 17.1 mi from the heart of Shelter Island. Guests who stay at this 3-star hotel in Southampton can enjoy access to a restaurant and free parking, along with free WiFi. It's a favorite with Expedia travelers for its dining options and breakfast.
  • Southampton Inn is 13.5 mi from the center of Shelter Island. This 3-star hotel in Riverhead features a marina, free breakfast, and a restaurant. It's a favorite with Expedia travelers for its beach locale and comfortable rooms.

Dressing for Shelter Island

  • Between January and March, you can expect the daytime average to be around 52°F and the nighttime average to be 19°F
  • From April to June, temperatures average about 79°F during the day and 31°F at night
  • July through September averages 81°F during the day and 46°F at night
  • In October-December, the average temperature is 68°F during the day and 21°F at night
  • Shelter Island gets about 46.85 inches of rain per year
  • Hottest months are usually July and August with an average temperature of 80°F, while the coldest months are February and January with an average of 20°F

Frequently asked questions

Where is the best place to stay in Shelter Island?
Based on Expedia’s traveller preferences, Shelter Island Waterfront House With Dock And Private Beach is a top place to stay in Shelter Island. Other good choices for your stay in the area are Gurney’s Star Island Resort & Marina and Water’s Edge Resort & Spa.
If I need to cancel my hotel reservation in Shelter Island, will I receive a refund?
Yes! You’ll find that most hotel bookings are fully refundable if you cancel before the accommodation’s cancellation deadline, which in most cases is within 24 or 48 hours of the scheduled arrival. If your reservation is non-refundable, you might be able to cancel it and receive a refund within a 24-hour period of your booking. Add your dates and click on “Search”, then you can use the “free cancellation” filter to get the best options available in Shelter Island.
What are some accommodations with pools in Shelter Island?

Recent Reviews in Shelter Island

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