Shelter Island
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10 Best Hotels in Shelter Island

Image for Gurney’s Star Island Resort & Marina
3.5 out of 5
32 Star Island Rd, Montauk, NY
AU$337
per night
14 Oct. - 15 Oct.
4.1/5Very Good! (656 reviews)

"Great location, good brunch Average finish, slightly tired look, smallish beds"…"

Reviewed on 18 Sep. 2019

Gurney’s Star Island Resort & Marina
Image for Gurney's Montauk Resort & Seawater Spa
4 out of 5
290 Old Montauk Highway, Montauk, NY
AU$479
per night
14 Oct. - 15 Oct.
4.3/5Excellent! (298 reviews)

"Amazing property. Went on a whim to celebrate an anniversary. The staff bent over backwards to accommodate our request for another room. Our original room had an obstructed view of the ocean due to a tent being placed for an event. They quickly moved us to another room with a stunning view of the ..."…"

Reviewed on 9 Sep. 2019

Gurney's Montauk Resort & Seawater Spa
Image for Saybrook Point Inn, Marina and Spa
3.5 out of 5
2 Bridge St, Old Saybrook, CT
Free CancellationReserve now, pay when you stay
AU$368
per night
15 Oct. - 16 Oct.
4.7/5Exceptional! (230 reviews)

"I had a wonderful room with full-water view, overlooking the marina, restaurant, and outdoor pool. Given that there were several weddings during my stay (three nights), there was more noise than I would have anticipated, but I was in a holiday mood so it didn't phase me. Note that swimmers in the ..."…"

Reviewed on 17 Sep. 2019

Saybrook Point Inn, Marina and Spa
Image for Water's Edge Resort & Spa
3.5 out of 5
1525 Boston Post Road, Westbrook, CT
Free CancellationReserve now, pay when you stay
AU$344
per night
14 Oct. - 15 Oct.
4.2/5Excellent! (343 reviews)

"It is nice ocean views. There are very cozy places."…"

Reviewed on 13 Sep. 2019

Water's Edge Resort & Spa
Image for Marram
4 out of 5
21 Oceanview Terrace, Montauk, NY
AU$342
per night
22 Sep. - 23 Sep.
4.3/5Excellent! (55 reviews)

"Mini Resort in beautiful Montauk! Great location-clean-friendly staff-nice rooms."…"

Reviewed on 15 Sep. 2019

Marram
Image for Sound View Greenport
3 out of 5
58775 Route 48, Greenport, NY
AU$369
per night
24 Sep. - 25 Sep.
4/5Very Good! (100 reviews)

"Wow! Amazing views. Excellent service. Everyone on the property was very very friendly. Very close to the town of Greenport and a lot of different wineries. You can't touch the views and sunsets. Will be back for sure."…"

Reviewed on 10 Sep. 2019

Sound View Greenport
Image for Bayview Resort
2.5 out of 5
53 West Tiana Road, Hampton Bays, NY
AU$304
per night
24 Sep. - 25 Sep.
4.2/5Very Good! (156 reviews)

"Great place, I really enjoyed my stay. The staff was nice and friendly, rooms were clean and comfortable. Great for family vacation."…"

Reviewed on 2 Sep. 2019

Bayview Resort
Image for Montauk Manor
3.5 out of 5
236 Edgemere St., Montauk, NY
AU$204
per night
15 Oct. - 16 Oct.
4.3/5Excellent! (114 reviews)

"Love the Manor- it was my 5th stay here and again it didn't disappoint. Clean comfy rooms, the whole vibe of the place is great. We used the indoor pool (had some cool weather). I'll definitely be back again!"…"

Reviewed on 2 Sep. 2019

Montauk Manor
Image for Kenny's Tipperary Inn
2 out of 5
432 West Lake Drive, Montauk, NY
AU$179
per night
23 Sep. - 24 Sep.
4/5Very Good! (315 reviews)

"We had a very relaxing & enjoyable stay. They gave us a late check out so we could have a last walk on the beach in the morning. John was helpful & friendly."…"

Reviewed on 11 Sep. 2019

Kenny's Tipperary Inn
Image for Beachcomber at Montauk
3 out of 5
727 Old Montauk Highway, Montauk, NY
AU$218
per night
20 Oct. - 21 Oct.
4.5/5Wonderful! (118 reviews)

"Nice view of the ocean from room balcony and short walk down to the beach. Bright and clean room."…"

Reviewed on 18 Sep. 2019

Beachcomber at Montauk
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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

More trip options

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