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
$291 nightly
The price is $334 total per night from Nov 12 to Nov 13
$334 total
Nov 12 - Nov 13
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 ...
Hospitality at its finest! Bed here was beyond comfortable❤️
Reviewed on Nov 5, 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 3 to Dec 4
$135 total
Dec 3 - Dec 4
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 ...
From the front desk receptionist to checking out, everything was perfect.
Reviewed on Nov 8, 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.
Staff was nice beautiful news
Reviewed on Nov 4, 2025

The Sagaponack
3720 Montauk Hwy, Wainscott, NY
$197 nightly
The price is $226 total per night from Nov 16 to Nov 17
$226 total
Nov 16 - Nov 17
Total with taxes and fees
A seasonal outdoor pool is featured at this bed & breakfast, along with free self parking. WiFi in public areas is free. A communal living room and luggage storage ...
An all round lovely experience. Perfect location and attention to detail. Lovely layout and amenities. It was a peaceful stay.
Reviewed on Nov 1, 2025

Sound View Greenport
58775 County Rd 48, Greenport, NY
$218 nightly
The price is $249 total per night from Nov 10 to Nov 11
$249 total
Nov 10 - Nov 11
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. We stay every year for a girls’ weekend. Rooms are great with a beautiful view. One thing the rooms could use are a standing closet for your clothes. Otherwise, it’s lovely.
Reviewed on Nov 2, 2025

Gurney's Montauk Resort & Seawater Spa
290 Old Montauk Highway, Montauk, NY
$363 nightly
The price is $414 total per night from Dec 1 to Dec 2
$414 total
Dec 1 - Dec 2
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 ...
A Truly Transcendent Weekend Escape: Impeccable Service and Luxury From the moment we arrived until the last minute of our departure, our anniversary weekend stay at Gurney’s was nothing short of perfection. This review is less about a hotel and more about an experience—one defined by luxury, comfort, ...
Reviewed on Nov 4, 2025

Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
$69 nightly
The price is $80 total per night from Nov 13 to Nov 14
$80 total
Nov 13 - Nov 14
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 ...
The room was very clean with soft towels. The sheets were clean but a bit rougher than I'm used to (I like silky sheets, not rough cotton) but the bed was comfortable and warm. The staff is very friendly too. A nice "basic" room that took care of our needs, didn't gross me out with smell or dirt ...
Reviewed on Nov 3, 2025

Quality Inn Old Saybrook - Westbrook
100 Essex Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $116 total per night from Nov 23 to Nov 24
$116 total
Nov 23 - Nov 24
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. ...
It was a nice clean hotel.
Reviewed on Oct 27, 2025

The Atlantic Hotel
1655 County Road 39, Southampton, NY
$151 nightly
The price is $172 total per night from Nov 10 to Nov 11
$172 total
Nov 10 - Nov 11
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 ...
Clean room. Courteous staff
Reviewed on Oct 29, 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.
Frequently asked questions
Recent Shelter Island hotel reviews by fellow wanderers

The Bentley Hotel Southampton
5 out of 5
Posted 12 hours ago
Travelocity Verified Review
"From the front desk receptionist to checking out, everything was perfect. "
A verified traveler stayed at The Bentley Hotel Southampton
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