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
$312 nightly
The price is $359 total per night from Dec 15 to Dec 16
$359 total
Dec 15 - Dec 16
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 ...
Excellent food, in addition to friendly and helpful staff.
Reviewed on Dec 1, 2025

The Bentley Hotel Southampton
161 Hills Station Rd Southampton NY
Fully refundableReserve now, pay when you stay
$118 nightly
The price is $135 total per night from Dec 11 to Dec 12
$135 total
Dec 11 - Dec 12
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 ...
Clean and quiet.
Reviewed on Nov 30, 2025

Beachcomber Resort at Montauk
727 Old Montauk Highway Montauk NY
This hotel features a gym and an outdoor tennis court. Enjoy the seasonal outdoor pool and perks like free WiFi. A sauna is also provided.
Beautiful views and so close to town. Walk right down the driveway to the ocean!
Reviewed on Nov 1, 2025

Montauk Blue Hotel
108 South Emerson Avenue Montauk NY
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.
I always have a 5/5 stay at Montauk Blue.
Reviewed on Nov 19, 2025

Offshore Montauk
71 S Emerson Ave Montauk NY
$166 nightly
The price is $190 total per night from Jan 1 to Jan 2
$190 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
An outdoor pool is featured at this hotel, along with free self parking. WiFi in public areas is free. A picnic area is also provided.
Room was spotless. Bed was so comfortable! Robert, the he head of the house and front desk was a pleasure and made our stay so welcoming and enjoyable.
Reviewed on Nov 23, 2025

Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
$210 nightly
The price is $242 total per night from Dec 16 to Dec 17
$242 total
Dec 16 - Dec 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 ...
Staff
Reviewed on Nov 30, 2025

Sound View Greenport
58775 County Rd 48 Greenport NY
$213 nightly
The price is $243 total per night from Dec 24 to Dec 25
$243 total
Dec 24 - Dec 25
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 ...
Great room with amazing views! Staff was fantastic and the food was great too
Reviewed on Nov 28, 2025

Gurney's Montauk Resort & Seawater Spa
290 Old Montauk Highway Montauk NY
$440 nightly
The price is $503 total per night from Jan 6 to Jan 7
$503 total
Jan 6 - Jan 7, 2026
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 ...
Great resort with a beautiful restaurant
Reviewed on Nov 22, 2025

Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundableReserve now, pay when you stay
$79 nightly
The price is $91 total per night from Dec 21 to Dec 22
$91 total
Dec 21 - Dec 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 ...
A welcoming place with some nice touches.
Reviewed on Nov 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 7 days ago
Travelocity Verified Review
"A welcoming place with some nice touches."
A verified traveler stayed at Pier Blue Inn Old Saybrook - Essex
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