Book Hotels in Shelter Island Heights, NY

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Top Shelter Island Heights hotels

The Chequit

The Chequit

3 out of 5
23 Grand Ave Shelter Island Heights NY
$184 nightly
The price is $210 total per night from Oct 8 to Oct 9
$210 total
Oct 8 - Oct 9
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A restaurant and a coffee shop are also provided.
"Amazing!! staff were lovely and hotel is so clean and so pretty"

Reviewed on Sep 16, 2026

Opens in a new windowThe Chequit
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
$218 nightly
The price is $251 total per night from Oct 7 to Oct 8
$251 total
Oct 7 - Oct 8
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 ...
"It was the perfect getaway- close to home. The property was beautiful, clean and peaceful. The beach could have been cleaner, but overall we loved our stay. The food served in their variety of restaurants was delicious. We will definitely return."

Reviewed on Sep 15, 2026

Opens in a new windowWater's Edge Resort & Spa
Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4 out of 5
290 Old Montauk Highway Montauk NY
$512 nightly
The price is $585 total per night from Oct 12 to Oct 13
$585 total
Oct 12 - Oct 13
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 ...
"Absolutely gorgeous stay!"

Reviewed on Sep 13, 2026

Opens in a new windowGurney's Montauk Resort & Seawater Spa
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Fully refundable
$93 nightly
The price is $107 total per night from Oct 14 to Oct 15
$107 total
Oct 14 - Oct 15
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 ...
"I have reported this property to the health department. The room was covered in mold. I had an asthma attack within minutes of walking in, and when I went back to the office to address, the concerns, it was met with great attitude until I pulled my phone out and started recording and then they said ..."

Reviewed on Sep 16, 2026

Opens in a new windowPier Blue Inn Old Saybrook - Essex
The Atlantic Hotel

The Atlantic Hotel

2.5 out of 5
1655 County Road 39 Southampton NY
$141 nightly
The price is $161 total per night from Oct 1 to Oct 2
$161 total
Oct 1 - Oct 2
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 ...
"I had room facing the busy street, but the room was well insulated and I did not hear the traffic from outside. Also, the floor plan was very functional. Linen was clean CLEAN, bed was SO comfortable And the amenities of small fridge, coffee maker, iron, -and 2 water bottles provided with each room ..."

Reviewed on Sep 15, 2026

Opens in a new windowThe Atlantic Hotel
The Pridwin Hotel

The Pridwin Hotel

4 out of 5
81 Shore Road Shelter Island Heights NY
$986 nightly
The price is $1,126 total per night from Sep 18 to Sep 19
$1,126 total
Sep 18 - Sep 19
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. ...
Opens in a new windowThe Pridwin Hotel
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
$253 nightly
The price is $290 total per night from Oct 1 to Oct 2
$290 total
Oct 1 - Oct 2
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 ...
Opens in a new windowSound View Greenport
Offshore Montauk

Offshore Montauk

4 out of 5
71 S Emerson Ave Montauk NY
$270 nightly
The price is $309 total per night from Sep 29 to Sep 30
$309 total
Sep 29 - Sep 30
Total with taxes and fees
This hotel features a gym and a seasonal outdoor pool. Enjoy the sauna and perks like free self parking and free WiFi. Express check-out and luggage storage ...
Opens in a new windowOffshore Montauk
Montauk Blue Hotel

Montauk Blue Hotel

2 out of 5
108 South Emerson Avenue Montauk NY
$163 nightly
The price is $186 total per night from Oct 18 to Oct 19
$186 total
Oct 18 - Oct 19
Total with taxes and fees
This hotel features an indoor pool and a hot tub. WiFi in public areas is free. A terrace, a picnic area, and luggage storage are also on offer.
Opens in a new windowMontauk Blue Hotel
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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

What are the top kid-friendly hotels in Shelter Island Heights?
Take some of the trials out of traveling with youngsters by booking a family-friendly hotel in Shelter Island Heights. From well-thought-out amenities to additional services, these stays feature perks that'll help make your visit an effortless one: House on Chase Creek will help make your break the most memorable one yet. It features an assortment of conveniences geared toward families, such as a nearby beach and front desk services. Otherwise, spend your Shelter Island Heights trip at Relax and Enjoy!. Make the most of a swimming pool, a playground and more here.
Where can I find cheap hotels in Shelter Island Heights?
At Travelocity you'll find really nice hotels in Shelter Island Heights at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Shelter Island Heights rather than in Shelter Island Heights. We may find you even better rates, too.
How do I find the best Shelter Island Heights hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Shelter Island Heights then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Shelter Island Heights?
The cheapest hotel in Shelter Island Heights is $107. This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Shelter Island Heights?
There are 4,682 hotels in Shelter Island Heights on Travelocity.
What are the best hotels in Shelter Island Heights?
Shelter Island Heights has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Shelter Island Heights for you!
When is the best time to visit Shelter Island Heights?
If you want the joy of a fun-filled trip in peak season, visit Shelter Island Heights during March, June and July. If you'd prefer the peace of off-season, book a stay during quieter months, such as April, November and December.
When is the cheapest time to stay in Shelter Island Heights?
Based on historic data is usually the cheapest month to visit Shelter Island Heights. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Shelter Island Heights?
There are multiple hotels in Shelter Island Heights that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Shelter Island Heights. We have plenty of kid-friendly hotels in Shelter Island Heights to choose from on Travelocity!
Why book a hotel in Shelter Island Heights through Travelocity?
Because we have the top hotels in Shelter Island Heights! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Shelter Island Heights on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Shelter Island Heights hotel reviews by fellow wanderers

The Chequit

The Chequit

5 out of 5
Posted 20 hours ago
Travelocity Verified Review
"Amazing!! staff were lovely and hotel is so clean and so pretty"
A verified traveler stayed at The Chequit
The Chequit

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