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
$354 nightly
The price is $404 total per night from May 10 to May 11
$404 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

Opens in a new windowThe Pridwin Hotel
The Bentley Hotel Southampton

The Bentley Hotel Southampton

2 out of 5
161 Hills Station Rd Southampton NY
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $154 total per night from May 17 to May 18
$154 total
May 17 - May 18
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 ...
I came for one night on a business trip and was absolutely impressed with the size of rhe rooms and how clean and well organized everything was! I will definetly be back! Even my doggie loved it

Reviewed on May 9, 2026

Opens in a new windowThe Bentley Hotel Southampton
Sag Harbor Inn

Sag Harbor Inn

3.5 out of 5
45 West Water Street Sag Harbor NY
$255 nightly
The price is $291 total per night from May 10 to May 11
$291 total
May 10 - May 11
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 ...
Beautiful hotel facing the harbor with courteous service and staff.

Reviewed on May 8, 2026

Opens in a new windowSag Harbor Inn
Montauk Yacht Club

Montauk Yacht Club

4 out of 5
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 ...
Unhinged wacko

Reviewed on May 6, 2026

Opens in a new windowMontauk Yacht Club
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
$326 nightly
The price is $373 total per night from May 10 to May 11
$373 total
May 10 - May 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 ...
Beautiful place to stay on a special getaway

Reviewed on May 7, 2026

Opens in a new windowSound View Greenport
Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4 out of 5
290 Old Montauk Highway Montauk NY
$493 nightly
The price is $563 total per night from May 12 to May 13
$563 total
May 12 - May 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 ...
I was skeptical at first since many comments are negative. As a woman of color, my experience was fantastic. The staff was lovely. I booked the ocean view room which was to my expectations. Overall 10/10 will return.

Reviewed on May 8, 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
$91 nightly
The price is $104 total per night from May 17 to May 18
$104 total
May 17 - May 18
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 ...
Very clean bare-bones hotel in a quiet location. Large rooms. Nice breakfast place across the road and a short drive to more services and stores. Helpful staff. Only criticism -- and it's an important one -- is that there were no friction strips or other kind of safety on the bathtub, so it was unexpectedly ...

Reviewed on May 7, 2026

Opens in a new windowPier Blue Inn Old Saybrook - Essex
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

2.5 out of 5
100 Essex Rd Old Saybrook CT
Fully refundable
$118 nightly
The price is $136 total per night from May 31 to Jun 1
$136 total
May 31 - Jun 1
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will ...
Clean and quality hotel ***. Friendly and helpful staff.

Reviewed on May 7, 2026

Opens in a new windowQuality Inn Old Saybrook - Westbrook
Montauk Manor

Montauk Manor

3.5 out of 5
236 Edgemere St. Montauk NY
$168 nightly
The price is $192 total per night from May 25 to May 26
$192 total
May 25 - May 26
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 ...
Opens in a new windowMontauk Manor
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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 $104. 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 4,823 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 Bentley Hotel Southampton

The Bentley Hotel Southampton

5 out of 5
Posted 2 hours ago
Travelocity Verified Review
"I came for one night on a business trip and was absolutely impressed with the size of rhe rooms and how clean and well organized everything was! I will definetly be back! Even my doggie loved it"
A verified traveler stayed at The Bentley Hotel Southampton
The Bentley Hotel Southampton

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