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 ...
Fridge and microwave, coffe
Reviewed on Apr 19, 2026

Sag Harbor Inn
45 West Water Street Sag Harbor NY
$225 nightly
The price is $257 total per night from Apr 21 to Apr 22
$257 total
Apr 21 - Apr 22
Total with taxes and fees
An outdoor pool is featured at this hotel, along with free self parking. Enjoy the free continental breakfast each morning. A fireplace in the lobby and luggage ...
We had a nice stay in room 106. Unfortunately, we asked for a wakeup call. The front desk crew went to room 107. The breakfast was quite extensive, and we had a good meal before we left. We would stay there again.
Reviewed on Apr 19, 2026

Offshore Montauk
71 S Emerson Ave Montauk NY
$258 nightly
The price is $295 total per night from Apr 30 to May 1
$295 total
Apr 30 - May 1
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 ...
This hotel was very convenient, comfortable, and clean. It is right by the beach and close to restaurants and a market. Also pet friendly. I am glad I stayed here.
Reviewed on Apr 19, 2026

Montauk Manor
236 Edgemere St. Montauk NY
$168 nightly
The price is $192 total per night from Apr 21 to Apr 22
$192 total
Apr 21 - Apr 22
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 ...
We stayed in a 1 bedroom deluxe loft. Only downfall is how much and how loud the noise travels throughout the unit. Next stay will definitely be a 2 bedroom.
Reviewed on Apr 17, 2026

Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
$294 nightly
The price is $338 total per night from Apr 22 to Apr 23
$338 total
Apr 22 - Apr 23
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 ...
pleasant visit staff very friendly
Reviewed on Apr 16, 2026

The Harbor Front Inn
209 Front St Greenport NY
$223 nightly
The price is $255 total per night from Apr 26 to Apr 27
$255 total
Apr 26 - Apr 27
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 ...
Really nice property!
Reviewed on Apr 16, 2026

Montauk Yacht Club
32 Star Island Rd Montauk NY
$279 nightly
The price is $319 total per night from Apr 21 to Apr 22
$319 total
Apr 21 - Apr 22
Total with taxes and fees
This hotel features a private beach, a marina, and 2 restaurants. Traveling on business? Take advantage of the 5 conference rooms, along with free WiFi in public ...
Great stay.
Reviewed on Apr 16, 2026

Gurney's Montauk Resort & Seawater Spa
290 Old Montauk Highway Montauk NY
$541 nightly
The price is $618 total per night from Apr 21 to Apr 22
$618 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 ...
I checked in during a severe snowstorm and had to leave the hotel within 30 minutes due to the conditions. Despite barely using the room, I was charged $304.50 as a “service fee.” I later reached out to the hotel to request clarification and a possible adjustment, but I have not received any response ...
Reviewed on Apr 20, 2026

Sound View Greenport
58775 County Rd 48 Greenport NY
$244 nightly
The price is $279 total per night from May 3 to May 4
$279 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 ...
View is stunning but rooms feel dated. Bathroom is extremely tiny and terrace had uncomfortable furniture.
Reviewed on Apr 18, 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
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5 Star Hotels
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Recent Shelter Island hotel reviews by fellow wanderers

Gurney's Montauk Resort & Seawater Spa
1 out of 5
Posted 18 hours ago
Travelocity Verified Review
"I checked in during a severe snowstorm and had to leave the hotel within 30 minutes due to the conditions. Despite barely using the room, I was charged $304.50 as a “service fee.”
I later reached out to the hotel to request clarification and a possible adjustment, but I have not received any response to this day.
I understand that policies may apply, but charging such a significant amount for a stay of less than an hour—especially under unavoidable weather conditions—feels unreasonable and disappointing.
The lack of communication from the hotel only adds to the frustration. I would appreciate a proper explanation and a fair resolution."
A verified traveler stayed at Gurney's Montauk Resort & Seawater Spa
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