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
$136 nightly
The price is $155 total per night from Apr 19 to Apr 20
$155 total
Apr 19 - Apr 20
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 ...
Spacious suite. Wish our stay was longer. Very clean, lots of special touches. Great staff.
Reviewed on Apr 2, 2026

Offshore Montauk
71 S Emerson Ave Montauk NY
$256 nightly
The price is $293 total per night from Apr 23 to Apr 24
$293 total
Apr 23 - Apr 24
Total with taxes and fees
The hotel's outdoor pool, 24-hour gym, and 2 bars/lounges are among the featured amenities. Enjoy a meal from the restaurant and perks like free self parking ...
Imagine a Super 8 motel or even something lower‑level that just put in new furniture and a new bathroom, but everything else stayed the same. It’s really not worth this price, to be honest. The rooms are clean but actually very small, and the hotel isn’t on the beach, there’s a dune and a road in ...
Reviewed on Apr 5, 2026

Montauk Manor
236 Edgemere St. Montauk NY
$168 nightly
The price is $192 total per night from Apr 23 to Apr 24
$192 total
Apr 23 - Apr 24
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 ...
Took a chance for last minute spring break getaway the pictures looked really nice and I have to say in person was actually better than the pictures! You really never know what you are going to get and this case I really felt we got better than what was listed. We stayed for an overnight but we definitely ...
Reviewed on Apr 8, 2026

Hyatt Place Long Island East End
451 East Main Street Riverhead NY
Fully refundableReserve now, pay when you stay
$142 nightly
The price is $162 total per night from Apr 19 to Apr 20
$162 total
Apr 19 - Apr 20
Total with taxes and fees
A marina, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center and ...
The staff tending the front desk / bar were amazing, very friendly and helpful!
Reviewed on Apr 8, 2026

Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
$263 nightly
The price is $302 total per night from Apr 22 to Apr 23
$302 total
Apr 22 - Apr 23
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 ...
Yes, we found everything we needed.
Reviewed on Apr 7, 2026

The Harbor Front Inn
209 Front St Greenport NY
$194 nightly
The price is $222 total per night from Apr 22 to Apr 23
$222 total
Apr 22 - Apr 23
Total with taxes and fees
This hotel features a 24-hour gym and a seasonal outdoor pool. Business travelers can take advantage of the free WiFi in public areas. Enjoy the free continental ...
Room was excellent and the beds were very comfortable. We went just prior to the season start so things were very calm. If i was to take issue with one thing; it would have been the shower was cool and never got hot. Not cold...but could have been warmer.
Reviewed on Apr 3, 2026

Gurney's Montauk Resort & Seawater Spa
290 Old Montauk Highway Montauk NY
$535 nightly
The price is $611 total per night from Apr 21 to Apr 22
$611 total
Apr 21 - Apr 22
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 ...
WE HAD A LOVELY WEEKEND. SERVICE WAS EXCELLENT.
Reviewed on Apr 6, 2026

Sound View Greenport
58775 County Rd 48 Greenport NY
$229 nightly
The price is $262 total per night from May 3 to May 4
$262 total
May 3 - May 4
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 ...
Bathroom very clean. Staff is super friendly. Ate at the restaurant and it was delicious.
Reviewed on Apr 6, 2026

Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundable
$79 nightly
The price is $91 total per night from Apr 15 to Apr 16
$91 total
Apr 15 - Apr 16
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 ...
room was clean and fresh. staff ere helpful and accommodating.
Reviewed on Apr 7, 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
Frequently asked questions
Recent Shelter Island hotel reviews by fellow wanderers

Montauk Manor
5 out of 5
Posted 20 hours ago
Travelocity Verified Review
"Took a chance for last minute spring break getaway the pictures looked really nice and I have to say in person was actually better than the pictures! You really never know what you are going to get and this case I really felt we got better than what was listed.
We stayed for an overnight but we definitely be back for two to three nights in September.
Staff was so lovely, the grounds are beautiful, clean and well kept. You cannot beat this view, room was spotless and had everything a family of four could need but most of all I appreciated the clean and updated furniture.
The hotel offers a shuttle in to town that we did not need but I can see how in the summer would be really helpful.
Indoor pool was open until 9pm with a lifeguard, our kids has a blast swimming after visiting the lighthouse and having dinner.
There was a cute playground by the lighthouse our kids really enjoyed after touring the lighthouse itself.
The restaurant in the hotel was not open in the off season time but it was easy enough to take a ride in to town & grab coffee’s. There are coffee pots in the room but you would need to bring coffee to brew and whatever you add to your coffee. My only suggestion for off peak season to the hotel would be a mini coffee bar in the lobby but honestly this hotel is perfect otherwise.
Families & couples will love it here there is something for everyone. I really don’t right reviews but other people’s reviews helped me book this so paying it forward."
A verified traveler stayed at Montauk Manor
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