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Montauk Manor
3.5 out of 5
236 Edgemere St., Montauk, NY
The price is AU$189 per night from 13 Oct. to 14 Oct.
30.61 km from city centre
4.5/5Wonderful! (306 reviews)

"Restaurant was closed and hotel had no coffee/tea station available. Entrance was far from parking lot- got soaked going in. Otherwise the Pool was great, rooms very clean. Nice place!"…"

Reviewed on 3 Sep. 2020

Montauk Manor
Shelter Island Waterfront House With Dock And Private Beach
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0.69 km from city centre
5/5Exceptional! (9 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
4.3/5Excellent! (4 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

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New Listing: Renovated & Modern, Waterviews, Walk to Beach, Heated Pool/hot Tub
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
4.9/5Exceptional! (7 reviews)
Cute house, lovely pool, but be aware of Lay-out

"The hosts were great, the setting and pool were lovely, but the house and some amenities were not represented exactly right. There are 4 bedrooms, but 2 upstairs are for kids, given the ladder that has to be climbed to reach them. One of the downstairs bedrooms doesn’t have an air conditioner . There ..."…"

Reviewed on 16 Aug. 2020

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$549 per night from 20 Sep. to 21 Sep.
31.95 km from city centre
4.1/5Very Good! (731 reviews)

"Very very nice, had one interaction where someone was rude to us but other than that had a really really nice time!"…"

Reviewed on 9 Sep. 2020

Gurney’s Star Island Resort & Marina
Water's Edge Resort & Spa
3.5 out of 5
1525 Boston Post Road, Westbrook, CT
Free cancellationReserve now, pay when you stay
The price is AU$330 per night from 20 Sep. to 21 Sep.
26.82 km from city centre
4.3/5Excellent! (459 reviews)

"Amazing resort following all Covid protocol, super clean, great staff, lots of dining options!"…"

Reviewed on 13 Sep. 2020

Water's Edge Resort & Spa
Saybrook Point Resort & Marina
3.5 out of 5
2 Bridge St, Old Saybrook, CT
Free cancellationReserve now, pay when you stay
The price is AU$374 per night from 1 Oct. to 2 Oct.
25.17 km from city centre
4.7/5Exceptional! (355 reviews)

"I believe this was my third stay at Saybrook and I plan on returning. Even before COVID standards, the rooms and other common areas were always very clean. I would say just pay attention to vent cleaning in the room but that's just me being picky because I'm allergic to dust."…"

Reviewed on 16 Sep. 2020

Saybrook Point Resort & Marina
Marram
4 out of 5
21 Oceanview Terrace, Montauk, NY
Free cancellationReserve now, pay when you stay
The price is AU$404 per night from 19 Oct. to 20 Oct.
31.71 km from city centre
4.5/5Wonderful! (42 reviews)

"The room with the ocean view was perfect and bed was super comfy. The beach and pool were so convenient for a weekend getaway. The restaurant- Il buco was so good- healthy yet very tasty food. My only wish is that we would have stayed longer!"…"

Reviewed on 29 Aug. 2020

Marram
Capri
3.5 out of 5
281 County Road 39A, Southampton, NY
Free cancellationReserve now, pay when you stay
The price is AU$404 per night from 20 Sep. to 21 Sep.
18.81 km from city centre
3/5 (101 reviews)

"Super cute hotel, clean, staff was great and welcoming. It is self service mode but I did not mind it. I loved how cute were the room and the pool area."…"

Reviewed on 8 Aug. 2020

Capri
Gurney's Montauk Resort & Seawater Spa
4 out of 5
290 Old Montauk Highway, Montauk, NY
The price is AU$671 per night from 18 Oct. to 19 Oct.
27.47 km from city centre
4.3/5Excellent! (350 reviews)

"Great customer service and room service. I will be coming back ."…"

Reviewed on 20 Jun. 2020

Gurney's Montauk Resort & Seawater Spa
The Atlantic Hotel
2.5 out of 5
1655 County Road 39, Southampton, NY
The price is AU$193 per night from 1 Oct. to 2 Oct.
21.61 km from city centre
3.3/5 (530 reviews)

"Very nice and clean place. Perfect for a family trip. My family enjoyed it"…"

Reviewed on 29 Aug. 2020

The Atlantic Hotel
Haven Montauk
2.5 out of 5
533 Westlake Drive, Montauk, Montauk, NY
The price is AU$221 per night from 21 Sep. to 22 Sep.
31.24 km from city centre
4.4/5Wonderful! (152 reviews)

"Great spot! Clean space : room was nicely redone and large. Friendly : staff was sweet and helpful. Location : walkikg distance to beach and to Gosman’s dock. Safe and family/kid-friendly. Amenities: pool great for kids and firepit area absolutely adorable. Overall : great stay for someone who always ..."…"

Reviewed on 5 Sep. 2020

Haven 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

Frequently asked questions

Where is the best place to stay in Shelter Island?
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 accommodation options with pools in Shelter Island?

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