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
$145 nightly
The price is $166 total per night from May 21 to May 22
$166 total
May 21 - May 22
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 ...
Great for dogs - huge fenced yard
Reviewed on May 11, 2026

Sag Harbor Inn
45 West Water Street Sag Harbor NY
$315 nightly
The price is $360 total per night from May 25 to May 26
$360 total
May 25 - May 26
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 ...
Great location, seemed a little outdated for the area. Breakfast was so so, didn't seem fresh. Late check-in was very helpful.
Reviewed on May 10, 2026

Montauk Manor
236 Edgemere St. Montauk NY
$185 nightly
The price is $212 total per night from May 21 to May 22
$212 total
May 21 - May 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 ...
Cute place great views would go back in the summer
Reviewed on May 11, 2026

Montauk Blue Hotel
108 South Emerson Avenue Montauk NY
$230 nightly
The price is $263 total per night from May 18 to May 19
$263 total
May 18 - May 19
Total with taxes and fees
This hotel features an indoor pool and a hot tub. A terrace, a picnic area, and luggage storage are also on offer.
Beautiful ocean front room. However, I wasn’t aware I would be charged an extra 35 dollars per day. She said it was a facility fee
Reviewed on May 4, 2026

Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
$239 nightly
The price is $275 total per night from May 21 to May 22
$275 total
May 21 - May 22
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 ...
We had a nice stay. Enjoyed having a drink at the bar and listening to the band. Had a nice breakfast in the morning. No major complaints, but for the price and style of the hotel I expected it to be cleaner. One of my drinks in the bar had a dirty ice cube and the glassware and plates at breakfast ...
Reviewed on May 14, 2026

Montauk Yacht Club
32 Star Island Rd Montauk NY
$347 nightly
The price is $396 total per night from May 17 to May 18
$396 total
May 17 - May 18
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 ...
Unhinged wacko
Reviewed on May 6, 2026

Gurney's Montauk Resort & Seawater Spa
290 Old Montauk Highway Montauk NY
$593 nightly
The price is $677 total per night from May 17 to May 18
$677 total
May 17 - May 18
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 ...
Stellar staff who made us feel most welcome. Loved the diversity of the team. Unforgettable scenery and experiences. We will definitely come back!
Reviewed on May 11, 2026

Sound View Greenport
58775 County Rd 48 Greenport NY
$358 nightly
The price is $409 total per night from May 27 to May 28
$409 total
May 27 - May 28
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 ...
They charged us for parking in front of our room. Unbelievable. We stayed there in April, off season, the motel was empty.
Reviewed on May 11, 2026

Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundable
$77 nightly
The price is $89 total per night from May 21 to May 22
$89 total
May 21 - May 22
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 ...
Excellent location. Parking great and surrounding area abounds with things to do while visiting.
Reviewed on May 13, 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

Water's Edge Resort & Spa
4 out of 5
Posted 2 hours ago
Travelocity Verified Review
"We had a nice stay. Enjoyed having a drink at the bar and listening to the band. Had a nice breakfast in the morning.
No major complaints, but for the price and style of the hotel I expected it to be cleaner. One of my drinks in the bar had a dirty ice cube and the glassware and plates at breakfast had some spots on them (looked like dried food that didn’t come off in dishwasher)
"
A verified traveler stayed at Water's Edge Resort & Spa
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