Book Hotels in Shelter Island Heights, NY

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Top Shelter Island Heights hotels

The Pridwin Hotel

The Pridwin Hotel

4 out of 5
81 Shore Road Shelter Island Heights NY
$666 nightly
The price is $761 total per night from Aug 31 to Sep 1
$761 total
Aug 31 - Sep 1
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. ...
"Amazon stay. They made our anniversary an unforgettable experience"

Reviewed on Aug 3, 2026

Opens in a new windowThe Pridwin Hotel
Offshore Montauk

Offshore Montauk

4 out of 5
71 S Emerson Ave Montauk NY
$557 nightly
The price is $636 total per night from Aug 4 to Aug 5
$636 total
Aug 4 - Aug 5
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 ...
"The room was clean, Staff was excellent, beach area and pool were great. Manager named Lucas and other staff members were always around and very helpful"

Reviewed on Jul 29, 2026

Opens in a new windowOffshore Montauk
Montauk Manor

Montauk Manor

3.5 out of 5
236 Edgemere St. Montauk NY
$481 nightly
The price is $549 total per night from Aug 17 to Aug 18
$549 total
Aug 17 - Aug 18
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 ...
"Pool parking bar even an excellent shuttle to most spots in Montauk JUST A PERFECT SET UP"

Reviewed on Aug 2, 2026

Opens in a new windowMontauk Manor
The Chequit

The Chequit

3 out of 5
23 Grand Ave Shelter Island Heights NY
$383 nightly
The price is $437 total per night from Aug 17 to Aug 18
$437 total
Aug 17 - Aug 18
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.
"It’s a beautiful property with a fun bar and delicious restaurant . The rooms were beautiful and the bed was super comfortable"

Reviewed on Jul 22, 2026

Opens in a new windowThe Chequit
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
$365 nightly
The price is $417 total per night from Sep 2 to Sep 3
$417 total
Sep 2 - Sep 3
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 in town getaway"

Reviewed on Aug 3, 2026

Opens in a new windowSound View Greenport
The Atlantic Hotel

The Atlantic Hotel

2.5 out of 5
1655 County Road 39 Southampton NY
$271 nightly
The price is $310 total per night from Aug 4 to Aug 5
$310 total
Aug 4 - Aug 5
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 ...
"Just a great experience across the board!"

Reviewed on Aug 3, 2026

Opens in a new windowThe Atlantic Hotel
West Neck Guesthouse

West Neck Guesthouse

3.5 out of 5
31 W Neck Rd Shelter Island Heights NY
$314 nightly
The price is $358 total per night from Aug 4 to Aug 5
$358 total
Aug 4 - Aug 5
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 garden and a picnic area are also ...
Opens in a new windowWest Neck Guesthouse
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
$104 nightly
The price is $120 total per night from Aug 25 to Aug 26
$120 total
Aug 25 - Aug 26
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 ...
Opens in a new windowPier Blue Inn Old Saybrook - Essex
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
$264 nightly
The price is $304 total per night from Aug 31 to Sep 1
$304 total
Aug 31 - Sep 1
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 ...
Opens in a new windowWater's Edge Resort & Spa
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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 $120. 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 4,780 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 Pridwin Hotel

The Pridwin Hotel

5 out of 5
Posted 1 hour ago
Travelocity Verified Review
"Amazon stay. They made our anniversary an unforgettable experience"
A verified traveler stayed at The Pridwin Hotel
The Pridwin Hotel

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