Book Hotels in Shelter Island, NY
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Top Shelter Island hotels

Saybrook Point Resort & Marina
2 Bridge St, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
$277 nightly
The price is $318 total per night from Nov 19 to Nov 20
$318 total
Nov 19 - Nov 20
Total with taxes and fees
A full-service spa, a marina, and 2 outdoor pools are all featured at this smoke-free hotel. Traveling on business? Take advantage of the free WiFi in public ...
"Location"
Reviewed on Oct 14, 2025

The Bentley Hotel Southampton
161 Hills Station Rd, Southampton, NY
Fully refundableReserve now, pay when you stay
$148 nightly
The price is $169 total per night from Oct 22 to Oct 23
$169 total
Oct 22 - Oct 23
Total with taxes and fees
A seasonal outdoor pool, free self parking, and laundry facilities are featured at this hotel. If you want to take your pet along, this pet-friendly property ...
"It was very spacious!"
Reviewed on Oct 17, 2025

Montauk Blue Hotel
108 South Emerson Avenue, Montauk, NY
$119 nightly
The price is $136 total per night from Nov 9 to Nov 10
$136 total
Nov 9 - Nov 10
Total with taxes and fees
This hotel features an indoor pool and a hot tub. WiFi in public areas is free. Self parking, a terrace, and a picnic area are also offered.
"Didn’t get to stay the night had a family emergency had to leave an hour after I checked in. Hope to get credited for another stay in the future. Staff was very nice."
Reviewed on Oct 13, 2025

Marram
21 Oceanview Terrace, Montauk, NY
$283 nightly
The price is $323 total per night from Oct 29 to Oct 30
$323 total
Oct 29 - Oct 30
Total with taxes and fees
A seasonal outdoor pool, free self parking, and wedding services are featured at this hotel. WiFi in public areas is free. A terrace, a garden, and luggage storage ...
"We came during terrible weather and couldn’t enjoy the amenities but the view and overall property is beautiful. Johnny at the front desk was very friendly and helpful."
Reviewed on Oct 13, 2025

Sound View Greenport
58775 County Rd 48, Greenport, NY
$266 nightly
The price is $304 total per night from Oct 26 to Oct 27
$304 total
Oct 26 - Oct 27
Total with taxes and fees
A private beach and a restaurant are featured at this smoke-free hotel. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Unwind with ...
"There was some deck furniture that needed repair. No microwave?? Why?"
Reviewed on Oct 9, 2025

Gurney's Montauk Resort & Seawater Spa
290 Old Montauk Highway, Montauk, NY
$330 nightly
The price is $377 total per night from Nov 4 to Nov 5
$377 total
Nov 4 - Nov 5
Total with taxes and fees
This resort features a private beach, a full-service spa, and 2 restaurants. Relax with beach cabanas and sun loungers, and cool off with a drink at the beachside ...
"We had a lovely one night stay. Everyone was very friendly. Having my dogs there was a treat. The spa was great and relaxing. GIGI’s restaurant is a must. The only complaint I have is that the bedclothes need to be updated. They were torn/frayed in multiple places. Other than that it was a great ..."
Reviewed on Oct 11, 2025

Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
$80 nightly
The price is $92 total per night from Oct 23 to Oct 24
$92 total
Oct 23 - Oct 24
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers ...
"The staff were super nice. The room was clean. For the price point it was a good value."
Reviewed on Oct 17, 2025

Quality Inn Old Saybrook - Westbrook
100 Essex Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
$94 nightly
The price is $108 total per night from Nov 2 to Nov 3
$108 total
Nov 2 - Nov 3
Total with taxes and fees
This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. ...
"Our stay was just what we needed. Breakfast was full of choices and and plenty to eat and drink. A perfect stop in a lovely town."
Reviewed on Oct 12, 2025

The Atlantic Hotel
1655 County Road 39, Southampton, NY
$138 nightly
The price is $158 total per night from Nov 3 to Nov 4
$158 total
Nov 3 - Nov 4
Total with taxes and fees
This hotel's 2 outdoor tennis courts and outdoor pool are among the featured amenities. Guests will appreciate free perks like free self parking and WiFi in ...
"Great stay overall. Only suggestion would be to put a light on the side of the building."
Reviewed on Oct 13, 2025
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.
Frequently asked questions
Recent Shelter Island hotel reviews by fellow wanderers

Offshore Montauk
5 out of 5
Posted 3 days ago
Travelocity Verified Review
"Beautifully renovated , super clean property. High quality sheets, towels, very comfortable bed. We enjoyed easy access to the beach and short distance to many dining options. Had wonderful stay and can't wait to come back."
A verified traveler stayed at Offshore Montauk
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