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
$140 nightly
The price is $160 total per night from Apr 26 to Apr 27
$160 total
Apr 26 - Apr 27
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 ...
The hotel is clean
Reviewed on Apr 16, 2026

Offshore Montauk
71 S Emerson Ave Montauk NY
$255 nightly
The price is $291 total per night from Apr 23 to Apr 24
$291 total
Apr 23 - Apr 24
Total with taxes and fees
This hotel features an outdoor pool and a gym. Enjoy the steam room and perks like free self parking and free WiFi. Express check-out and luggage storage are ...
Very nice rooms! Clean and the location is great!
Reviewed on Apr 12, 2026

Montauk Manor
236 Edgemere St. Montauk NY
$168 nightly
The price is $192 total per night from Apr 20 to Apr 21
$192 total
Apr 20 - Apr 21
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 kitchen was perfect, only thing missing was utensils. There is a local store on the way to the manor to pick some of those staples up from.
Reviewed on Apr 13, 2026

Hyatt Place Long Island East End
451 East Main Street Riverhead NY
Fully refundableReserve now, pay when you stay
$148 nightly
The price is $169 total per night from Apr 29 to Apr 30
$169 total
Apr 29 - Apr 30
Total with taxes and fees
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 ...
Beautiful
Reviewed on Apr 12, 2026

Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
$265 nightly
The price is $304 total per night from Apr 19 to Apr 20
$304 total
Apr 19 - Apr 20
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 ...
Front desk staff were amazing! The bar staff were very attentive and friendly. Rooms are clean, but definitely dated.
Reviewed on Apr 13, 2026

The Harbor Front Inn
209 Front St Greenport NY
$224 nightly
The price is $256 total per night from Apr 19 to Apr 20
$256 total
Apr 19 - Apr 20
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 ...
Lovely place for a quiet getaway off-season. Loved this place and will be back. Only disappointment was morning coffee … lacking flavor and lukewarm … but there is a wonderful shop just a few doors down with very good coffee. Nespresso machine in room.
Reviewed on Apr 13, 2026

Gurney's Montauk Resort & Seawater Spa
290 Old Montauk Highway Montauk NY
$535 nightly
The price is $611 total per night from Apr 23 to Apr 24
$611 total
Apr 23 - Apr 24
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 ...
Our family of four stayed for 3 nights in a two bedroom suite with ocean views. We booked it last minute for spring break. Overall, we had an amazing time and enjoyed our stay despite the cold temps. The room was clean. I saw no obvious signs of aging of furniture, fittings and walls - a huge plus ...
Reviewed on Apr 14, 2026

Sound View Greenport
58775 County Rd 48 Greenport NY
$254 nightly
The price is $290 total per night from May 3 to May 4
$290 total
May 3 - May 4
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 ...
We love the Sound View. As a school social worker, I sometimes REALLY need to reset. There is no better place to do it than here with the most amazing views! We have been coming 3x a year with our pup. Great staff and restaurant! The hotel really tries to accommodate requests, such as a certain room ...
Reviewed on Apr 14, 2026

Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundable
$91 nightly
The price is $104 total per night from Apr 23 to Apr 24
$104 total
Apr 23 - Apr 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 ...
Yes
Reviewed on Apr 15, 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
Frequently asked questions
Recent Shelter Island hotel reviews by fellow wanderers

The Bentley Hotel Southampton
5 out of 5
Posted 8 hours ago
Travelocity Verified Review
"The hotel is clean"
A verified traveler stayed at The Bentley Hotel Southampton
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