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
$126 nightly
The price is $144 total per night from Jan 4 to Jan 5
$144 total
Jan 4 - Jan 5, 2026
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 ...
crystal clean, great location and PRICE! large rooms. plenty of space. absolutely amazing
Reviewed on Dec 14, 2025

Saybrook Point Resort & Marina
2 Bridge St Old Saybrook CT
Fully refundableReserve now, pay when you stay
$311 nightly
The price is $358 total per night from Jan 3 to Jan 4
$358 total
Jan 3 - Jan 4, 2026
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 ...
Friendly and helpful staff, wonderful dining experience at Fresh Salt
Reviewed on Dec 13, 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.
I always have a 5/5 stay at Montauk Blue.
Reviewed on Nov 19, 2025

Offshore Montauk
71 S Emerson Ave Montauk NY
$166 nightly
The price is $190 total per night from Jan 8 to Jan 9
$190 total
Jan 8 - Jan 9, 2026
Total with taxes and fees
An outdoor pool is featured at this hotel, along with free self parking. WiFi in public areas is free. A picnic area is also provided.
The room looked like it should have been in a much higher end hotel as it was recently refurbished. Very comfortable to be in as well as clean. Was very pleased for the price. Only downside was that the curtains let in far too much light.
Reviewed on Dec 13, 2025

Montauk Manor
236 Edgemere St. Montauk NY
$156 nightly
The price is $178 total per night from Jan 6 to Jan 7
$178 total
Jan 6 - Jan 7, 2026
Total with taxes and fees
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 ...
The room was very clean, comfortable and quiet. The hotel was decorated beautifully for the holidays. The pool area with hot tub was clean and enjoyable
Reviewed on Dec 15, 2025

Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
$244 nightly
The price is $281 total per night from Jan 1 to Jan 2
$281 total
Jan 1 - Jan 2, 2026
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 ...
Everything was wonderful. Staff was friendly, very clean,we enjoyed it.
Reviewed on Dec 20, 2025

The Harbor Front Inn
209 Front St Greenport NY
$178 nightly
The price is $203 total per night from Jan 22 to Jan 23
$203 total
Jan 22 - Jan 23, 2026
Total with taxes and fees
This hotel features a 24-hour gym and a seasonal outdoor pool. Business travelers can take advantage of the free WiFi in public areas. Enjoy the free continental ...
Welcoming and kind staff! Nice breakfast, wasn’t too over the top. Room was spacious and view was lovely! The elevator wasn’t working so they waved the parking fee which was so nice considering we were on the first floor and didn’t need the elevator. Gave 4 starts because our fridge wasn’t working ...
Reviewed on Dec 10, 2025

Gurney's Montauk Resort & Seawater Spa
290 Old Montauk Highway Montauk NY
$418 nightly
The price is $478 total per night from Jan 15 to Jan 16
$478 total
Jan 15 - Jan 16, 2026
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 ...
Everything was perfect. Staff, room, experience. Will definitely stay again.
Reviewed on Dec 14, 2025

Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundableReserve now, pay when you stay
$69 nightly
The price is $79 total per night from Dec 28 to Dec 29
$79 total
Dec 28 - Dec 29
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 ...
Nice, pet friendly facility with an amazing Indian restaurant next door!
Reviewed on Dec 14, 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
Frequently asked questions
Recent Shelter Island hotel reviews by fellow wanderers

Water's Edge Resort & Spa
5 out of 5
Posted 3 days ago
Travelocity Verified Review
"Everything was wonderful. Staff was friendly, very clean,we enjoyed it."
A verified traveler stayed at Water's Edge Resort & Spa
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