Book Hotels in Shelter Island, NY
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Top Shelter Island hotels

The Bentley Hotel Southampton
161 Hills Station Rd Southampton NY
Fully refundableReserve now, pay when you stay
The price is $151 total per night from Mar 16 to Mar 17
$151 total
per night
Mar 16 - Mar 17
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 ...
Clean room. The man at the office was very friendly.
Reviewed on Mar 10, 2026

Offshore Montauk
71 S Emerson Ave Montauk NY
The price is $181 total per night from Mar 15 to Mar 16
$181 total
per night
Mar 15 - Mar 16
This hotel features an outdoor pool and a steam room. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area is also ...
room in front of the street
Reviewed on Mar 9, 2026

Montauk Manor
236 Edgemere St. Montauk NY
The price is $164 total per night from Mar 24 to Mar 25
$164 total
per night
Mar 24 - Mar 25
3 outdoor tennis courts, an indoor pool, and a 24-hour gym are all featured at this smoke-free aparthotel. Enjoy the seasonal outdoor pool and perks like free ...
Always such a pleasure at the Manor.
Reviewed on Feb 28, 2026

Montauk Blue Hotel
108 South Emerson Avenue Montauk NY
This hotel features an indoor pool and a hot tub. A terrace, a picnic area, and luggage storage are also on offer.
Great view of sunrise and sunset
Reviewed on Jan 19, 2026

Hyatt Place Long Island East End
451 East Main Street Riverhead NY
The price is $129 total per night from Mar 29 to Mar 30
$129 total
per night
Mar 29 - Mar 30
A marina, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center and ...
Good hotel....could update the gym and provide microwave oven.....
Reviewed on Mar 2, 2026

Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
The price is $212 total per night from Apr 1 to Apr 2
$212 total
per night
Apr 1 - Apr 2
This smoke-free resort features a private beach, a full-service spa, and 3 restaurants. Relax with beach cabanas and sun loungers, and cool off with a drink ...
This was my first time at Water’s Edge and will definitely not be my last. Our stay was wonderful. Becky at the front desk was
Reviewed on Mar 7, 2026

Gurney's Montauk Resort & Seawater Spa
290 Old Montauk Highway Montauk NY
The price is $457 total per night from Mar 24 to Mar 25
$457 total
per night
Mar 24 - Mar 25
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 ...
I took my husband for a relaxing weekend for his birthday at Gurneys Resort. We had an ocean front room with a beautiful view! The room and resort was beautiful and clean. We hung out at GiGis bar a lot and the bar tenders were great! Super friendly and helpful! I loved our stay however I was truly ...
Reviewed on Mar 4, 2026

Sound View Greenport
58775 County Rd 48 Greenport NY
The price is $203 total per night from Mar 23 to Mar 24
$203 total
per night
Mar 23 - Mar 24
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 ...
Staff was over the top helpful, nice!!!! If you needed help or anything they were right on it for you Thank you do very much for making a sad trip for a loved ones memorial into something grateful!!
Reviewed on Mar 1, 2026

Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundable
The price is $105 total per night from Mar 22 to Mar 23
$105 total
per night
Mar 22 - Mar 23
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 ...
Very welcoming staff. Average accommodations but comfortable and convenient to supermarket.
Reviewed on Mar 9, 2026
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.
Hotels in Shelter Island with star-rating
Check Shelter Island Hotels by Star Rating

5 Star Hotels
2 properties
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Recent Shelter Island hotel reviews by fellow wanderers

The Bentley Hotel Southampton
5 out of 5
Posted 2 hours ago
Travelocity Verified Review
"Clean room. The man at the office was very friendly."
A verified traveler stayed at The Bentley Hotel Southampton
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