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Top Shelter Island Heights hotels

The Pridwin Hotel
81 Shore Road Shelter Island Heights NY
$355 nightly
The price is $406 total per night from May 10 to May 11
$406 total
May 10 - May 11
Total with taxes and fees
This smoke-free hotel features a private beach, a full-service spa, and a restaurant. Enjoy the gym and free perks like continental breakfast and free self parking. ...
Overall the places is nice, clean and great views
Reviewed on Oct 21, 2025

The Bentley Hotel Southampton
161 Hills Station Rd Southampton NY
Fully refundableReserve now, pay when you stay
$169 nightly
The price is $194 total per night from May 6 to May 7
$194 total
May 6 - May 7
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 check in check out , friendly staff, beautiful property & right in the middle of it all
Reviewed on May 3, 2026

Sag Harbor Inn
45 West Water Street Sag Harbor NY
$255 nightly
The price is $291 total per night from May 7 to May 8
$291 total
May 7 - May 8
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 ...
So clean! Loved the location.
Reviewed on Apr 27, 2026

Montauk Manor
236 Edgemere St. Montauk NY
$168 nightly
The price is $192 total per night from May 18 to May 19
$192 total
May 18 - May 19
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 ...
Great locations for sunset.
Reviewed on Apr 30, 2026

Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
$264 nightly
The price is $304 total per night from May 8 to May 9
$304 total
May 8 - May 9
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 ...
Incredible staff
Reviewed on Apr 30, 2026

Montauk Yacht Club
32 Star Island Rd Montauk NY
$299 nightly
The price is $341 total per night from May 11 to May 12
$341 total
May 11 - May 12
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 Montauk Yacht Club is a beautiful and relaxing getaway with a true coastal luxury feel. The property is well-maintained, with scenic waterfront views that make the entire experience feel special and refreshing. The rooms are comfortable and thoughtfully designed, offering a clean and modern aesthetic. ...
Reviewed on Apr 21, 2026

Gurney's Montauk Resort & Seawater Spa
290 Old Montauk Highway Montauk NY
$493 nightly
The price is $563 total per night from May 6 to May 7
$563 total
May 6 - May 7
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 ...
Couple weekend away from the kids. Loved the peace on off season. The spa was just amazing as well as the food / services at the restaurants. Staff was all so helpful and nice
Reviewed on May 3, 2026

Sound View Greenport
58775 County Rd 48 Greenport NY
$287 nightly
The price is $328 total per night from May 25 to May 26
$328 total
May 25 - May 26
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 rooms, great continental breakfast. Was upgraded to waterfront room!!
Reviewed on May 3, 2026

Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundable
$91 nightly
The price is $104 total per night from May 11 to May 12
$104 total
May 11 - May 12
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 ...
Parking was easy. Bed mattress terrible. Tired room and furnishings. Basic supplies.
Reviewed on Apr 28, 2026
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View all propertiesLowest 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.
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Recent Shelter Island Heights hotel reviews by fellow wanderers

Sleep Inn & Suites Niantic North
5 out of 5
Posted 5 hours ago
Travelocity Verified Review
"Convenient location while visiting in Hadlyme. Staff was friendly, breakfast staff was pleasant, room clean"
A verified traveler stayed at Sleep Inn & Suites Niantic North
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