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 27 to Apr 28
$160 total
Apr 27 - Apr 28
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 ...
This hotel was lovely. I enjoyed the decor, how spacious it was, the lawn and the couches to sit in outside. Truly, an amazing experience in every way. The staff was always welcoming and helpful. No complaints and I would definitely stay again if I come to the Hamptons!
Reviewed on Apr 13, 2026

Offshore Montauk
71 S Emerson Ave Montauk NY
$255 nightly
The price is $291 total per night from Apr 21 to Apr 22
$291 total
Apr 21 - Apr 22
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 15 to Apr 16
$192 total
Apr 15 - Apr 16
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
$140 nightly
The price is $160 total per night from Apr 29 to Apr 30
$160 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
$263 nightly
The price is $302 total per night from Apr 16 to Apr 17
$302 total
Apr 16 - Apr 17
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
$194 nightly
The price is $222 total per night from Apr 27 to Apr 28
$222 total
Apr 27 - Apr 28
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 21 to Apr 22
$611 total
Apr 21 - Apr 22
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
$228 nightly
The price is $260 total per night from May 4 to May 5
$260 total
May 4 - May 5
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
$83 nightly
The price is $95 total per night from Apr 15 to Apr 16
$95 total
Apr 15 - Apr 16
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 ...
Great place to stay on the shoreline. Privately owned so you.are supporting local businesses!
Reviewed on Apr 10, 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

Gurney's Montauk Resort & Seawater Spa
5 out of 5
Posted 7 hours ago
Travelocity Verified Review
"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 given the volume of people it must see.
We chose to have breakfasts, lunches and one evening's dinner outside of the resort. The only area I thought they could have done better is the consistency of the communication and countenance of the staff. Front desk was excellent - smiles, eye contact and clear communication. Cleaner was happy, smiles and positive. Gigi's maitre d' was polite and prompt but we're out of New York, it'll be nice to have some warmth through a smile and eye contact. Similarly, while one evening's waiter, Felix, was phenomenal in his ability to connect professionally with us, the next night's waiter did not. I can understand that they must see a variety of individuals every day and it can wear on their emotions (perhaps some individuals are rude to them?) but they are in customer facing roles and each new table is an opportunity to bring some warmth and enjoyment to a new customer's experience. We'd go again and adjust our expectations of Gigi's dining experience. "
A verified traveler stayed at Gurney's Montauk Resort & Seawater Spa
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