Book Hotels in Shelter Island, NY
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Top Shelter Island hotels

Saybrook Point Resort & Marina
2 Bridge St Old Saybrook CT
$253 nightly
The price is $291 total per night from Nov 30 to Dec 1
$291 total
Nov 30 - Dec 1
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 ...
Everything and everyone was fabulous!
Reviewed on Nov 19, 2025

The Bentley Hotel Southampton
161 Hills Station Rd Southampton NY
Fully refundableReserve now, pay when you stay
$103 nightly
The price is $118 total per night from Nov 24 to Nov 25
$118 total
Nov 24 - Nov 25
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 ...
Nice
Reviewed on Nov 17, 2025

Montauk Blue Hotel
108 South Emerson Avenue Montauk NY
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.
Location - beautiful view
Reviewed on Nov 10, 2025

Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
$175 nightly
The price is $202 total per night from Nov 23 to Nov 24
$202 total
Nov 23 - Nov 24
Total with taxes and fees
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 ...
The rooms were clean staff were great the place wonderful we love it
Reviewed on Nov 9, 2025

Sound View Greenport
58775 County Rd 48 Greenport NY
$203 nightly
The price is $232 total per night from Nov 23 to Nov 24
$232 total
Nov 23 - Nov 24
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 ...
Beautiful and unique property. We really enjoyed our weekend getaway
Reviewed on Nov 13, 2025

Gurney's Montauk Resort & Seawater Spa
290 Old Montauk Highway Montauk NY
$308 nightly
The price is $351 total per night from Dec 10 to Dec 11
$351 total
Dec 10 - Dec 11
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 ...
Beautiful view and accomodations. Enjoyed the bathhouse and hotel amenities
Reviewed on Nov 15, 2025

Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundableReserve now, pay when you stay
$71 nightly
The price is $82 total per night from Dec 1 to Dec 2
$82 total
Dec 1 - Dec 2
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 room was very clean with soft towels. The sheets were clean but a bit rougher than I'm used to (I like silky sheets, not rough cotton) but the bed was comfortable and warm. The staff is very friendly too. A nice "basic" room that took care of our needs, didn't gross me out with smell or dirt ...
Reviewed on Nov 3, 2025

Quality Inn Old Saybrook - Westbrook
100 Essex Rd Old Saybrook CT
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $116 total per night from Nov 30 to Dec 1
$116 total
Nov 30 - Dec 1
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. ...
Staff was kind. Easy, comfortable stay.
Reviewed on Nov 19, 2025

The Atlantic Hotel
1655 County Road 39 Southampton NY
$138 nightly
The price is $158 total per night from Dec 5 to Dec 6
$158 total
Dec 5 - Dec 6
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 ...
Clean room. Courteous staff
Reviewed on Oct 29, 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.
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

Quality Inn Old Saybrook - Westbrook
5 out of 5
Posted 2 days ago
Travelocity Verified Review
"Staff was kind. Easy, comfortable stay."
A verified traveler stayed at Quality Inn Old Saybrook - Westbrook
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