Book Hotels in Shelter Island, NY
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Top Shelter Island hotels

Saybrook Point Resort & Marina
2 Bridge St, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
$331 nightly
The price is $380 total per night from Nov 2 to Nov 3
$380 total
Nov 2 - Nov 3
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 ...
"Loved everything about this property. Location, Staff, Amenities. Decor and furniture beautiful."
Reviewed on Sep 24, 2025

Montauk Blue Hotel
108 South Emerson Avenue, Montauk, NY
$148 nightly
The price is $170 total per night from Oct 26 to Oct 27
$170 total
Oct 26 - Oct 27
Total with taxes and fees
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.
"Great to have a room right on the beach. Room was a little outdated. Otherwise, very nice stay."
Reviewed on Oct 1, 2025

Marram
21 Oceanview Terrace, Montauk, NY
$282 nightly
The price is $323 total per night from Oct 13 to Oct 14
$323 total
Oct 13 - Oct 14
Total with taxes and fees
A seasonal outdoor pool, free self parking, and wedding services are featured at this hotel. WiFi in public areas is free. A terrace, a garden, and luggage storage ...
Relax at the Marram
"Locations are d writhing, and the marran has this, right on the beach, watching whales, dolphins and spinning sharks from the comfort of the pool and/or beach…… lovely sitting area for drinks and dinner watching the sun go down. This is a hotel to savour on a nice night, we stayed the 18/19 sept, ..."
Reviewed on Sep 20, 2025

Sound View Greenport
58775 County Rd 48, Greenport, NY
$281 nightly
The price is $321 total per night from Oct 16 to Oct 17
$321 total
Oct 16 - Oct 17
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 ...
"Clean and beautiful view"
Reviewed on Sep 16, 2025

Montauk Yacht Club
32 Star Island Rd, Montauk, NY
$294 nightly
The price is $336 total per night from Oct 19 to Oct 20
$336 total
Oct 19 - Oct 20
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 ...
"The room just had ants by the beds."
Reviewed on Sep 28, 2025

Gurney's Montauk Resort & Seawater Spa
290 Old Montauk Highway, Montauk, NY
$416 nightly
The price is $476 total per night from Nov 2 to Nov 3
$476 total
Nov 2 - Nov 3
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 ...
"Amazing resort, very friendly staff, food and drinks are Amazing! We enjoyed our stay."
Reviewed on Sep 15, 2025

Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
$82 nightly
The price is $95 total per night from Oct 22 to Oct 23
$95 total
Oct 22 - Oct 23
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 ...
"Only issue....the refrigerator makes an annoying sound which is amlpified wearing hearing aids"
Reviewed on Sep 30, 2025

Quality Inn Old Saybrook - Westbrook
100 Essex Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
$94 nightly
The price is $108 total per night from Nov 2 to Nov 3
$108 total
Nov 2 - Nov 3
Total with taxes and fees
This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. ...
"Liked having and using pool. didn't realize there would be a swimming lesson going on at same time. As this was a quick stop over on our way to Bar Harbor, it fit our needs. Since the room was on the street side it was a bit noisy even with fan running all the time. The room was clean and comfortable ..."
Reviewed on Sep 28, 2025

The Atlantic Hotel
1655 County Road 39, Southampton, NY
$138 nightly
The price is $158 total per night from Nov 2 to Nov 3
$158 total
Nov 2 - Nov 3
Total with taxes and fees
This hotel's 2 outdoor tennis courts and outdoor pool are among the featured amenities. Guests will appreciate free perks like free self parking and WiFi in ...
"Really more of a motel not a hotel. Room was basic but adequate and clean. Close to Southampton. They were fully booked on one of the weekend days of our stay so rate that night was high for this type of lodging."
Reviewed on Sep 30, 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
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Recent Shelter Island hotel reviews by fellow wanderers

Pier Blue Inn Old Saybrook - Essex
5 out of 5
Posted 1 day ago
Travelocity Verified Review
"Only issue....the refrigerator makes an annoying sound which is amlpified wearing hearing aids"
A verified traveler stayed at Pier Blue Inn Old Saybrook - Essex
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