Book Hotels in Dering Harbor, NY

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Top Dering Harbor hotels

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
$170 nightly
The price is $194 total per night from May 14 to May 15
$194 total
May 14 - May 15
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

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 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 ...
Very nice clean quaint hotel , rooms very nice decor and beds comfortable! Would definitely stay here again if visiting the area !

Reviewed on May 5, 2026

Opens in a new windowSag Harbor Inn
The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 out of 5
61600 Main Rd Southold NY
$243 nightly
The price is $274 total per night from May 20 to May 21
$274 total
May 20 - May 21
Total with taxes and fees
This hotel features a bar/lounge, a coffee shop, and a communal living room. A business center, a picnic area, and express check-out are also on offer.
Very helpful staff. Room was very roomy (no pun intented) and appeared to be recently upgraded. Chit provided for continental breakfast at a local coffee shop that was very good. Definitely recommend.

Reviewed on May 5, 2026

Opens in a new windowThe Shoals Suites and Slips
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
$240 nightly
The price is $276 total per night from May 8 to May 9
$276 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

Opens in a new windowWater's Edge Resort & Spa
The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
209 Front St Greenport NY
$257 nightly
The price is $293 total per night from May 20 to May 21
$293 total
May 20 - May 21
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 ...
Spacious, well appointed rooms. Great location. The complimentary breakfast was cozy (nothing fancy but gets the job done). We stayed for three nights with a small dog in tow. The only surprise was that parking was not free ($29 per night) but there was plenty of free street parking available ...

Reviewed on Apr 27, 2026

Opens in a new windowThe Harbor Front Inn
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 ...
Clean rooms, great continental breakfast. Was upgraded to waterfront room!!

Reviewed on May 3, 2026

Opens in a new windowSound View Greenport
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 12 to May 13
$104 total
May 12 - May 13
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

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 26 to May 27
$136 total
May 26 - May 27
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 ...
Good value

Reviewed on May 4, 2026

Opens in a new windowQuality Inn Old Saybrook - Westbrook
North Fork Cottages & RV Resort

North Fork Cottages & RV Resort

3 out of 5
690 Queen St Greenport NY
$187 nightly
The price is $214 total per night from May 11 to May 12
$214 total
May 11 - May 12
Total with taxes and fees
A seasonal outdoor pool, free self parking, and laundry facilities are featured at this cottage. WiFi in public areas is free. A picnic area and barbecue grills ...
Opens in a new windowNorth Fork Cottages & RV Resort
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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 Dering Harbor?
From unique amenities to extra space, kid-friendly hotels are equipped with features that can help turn an everyday family vacation into an awesome one. These Dering Harbor options make traveling with children easy: The whole gang will enjoy their time at Shelter Island Chic. Free WiFi and clothes washing facilities are among the things that help make this place a popular option. Majestic Shelter Island retreat with three levels of living, just under an... is also a great choice. After a big day of exploring, come back home to your cozy room and perks like a king bed and a barbecue grill.
Where can I find cheap hotels in Dering Harbor?
At Travelocity you'll find really nice hotels in Dering Harbor 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 Dering Harbor rather than in Dering Harbor. We may find you even better rates, too.
How do I find the best Dering Harbor hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Dering Harbor 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 Dering Harbor?
The cheapest hotel in Dering Harbor 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 Dering Harbor?
There are 4,080 hotels in Dering Harbor on Travelocity.
What are the best hotels in Dering Harbor?
Dering Harbor 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 Dering Harbor for you!
When is the best time to visit Dering Harbor?
If you want the joy of a fun-filled trip in peak season, visit Dering Harbor during May, June and July. If you'd prefer the peace of off-season, book a stay during quieter months, such as December, January and February.
When is the cheapest time to stay in Dering Harbor?
Based on historic data is usually the cheapest month to visit Dering Harbor. 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 Dering Harbor?
There are multiple hotels in Dering Harbor 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 Dering Harbor. We have plenty of kid-friendly hotels in Dering Harbor to choose from on Travelocity!
Why book a hotel in Dering Harbor through Travelocity?
Because we have the top hotels in Dering Harbor! 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 Dering Harbor 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.

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