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Dering Harbor Vacation Rentals

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Our top choices for Dering Harbor vacation rentals

1. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (48 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
$275 nightly
The price is $314
Sep 13 - Sep 14
Total with taxes and fees
North Fork Resort

2. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (283 reviews)
"Great place!"
United States
Christine
$385 nightly
The price is $439
Sep 7 - Sep 8
Total with taxes and fees
Cliffside Resort Condominiums

3. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (47 reviews)
"Lovely place, very clean, host was very responsive. Thanks so much!"
United States
Marie H.
$329 nightly
The price is $376
Sep 10 - Sep 11
Total with taxes and fees
The SandPiper

4. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (41 reviews)
"Nice clean space, well appointed and easy walking access to downtown area."
United States
Molly G.
$329 nightly
The price is $376
Sep 8 - Sep 9
Total with taxes and fees
Aqua Vista

5. Harbor Heights

Harbor Heights
Pipes Cove
10.0 out of 10, Exceptional, (22 reviews)
"Close to the train, beach and restaurant, very convenient on foot"
United States
Nigel
$336 nightly
The price is $384
Sep 13 - Sep 14
Total with taxes and fees
Harbor Heights

6. Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
Pipes Cove
10.0 out of 10, Exceptional, (28 reviews)
"We had a great stay!! "
United States
Callie E.
$452 nightly
The price is $516
Sep 7 - Sep 8
Total with taxes and fees
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

7. American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.4 out of 10, Exceptional, (6 reviews)
"Great place! So nice."
United States
Paul F.
$393 nightly
The price is $449
Sep 7 - Sep 8
Total with taxes and fees
American Beech in Greenport - Petite King Room 7

8. Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, Exceptional, (8 reviews)
"Everything about Beach Block Hideaway was perfect! The house was absolutely immaculate, the kitchen well stocked with plenty of kitchenware, beds very comfortable. Easy walk to town. We have stayed at a number of homes when visiting Greenport over the years but this place is truly the best - highly recommend! "
United States
maureen f.
$480 nightly
The price is $548
Sep 8 - Sep 9
Total with taxes and fees
Beach Block Hideaway

9. Safari Tent Glamping,S10-CedarPt, East Hampton, NY

Safari Tent Glamping,S10-CedarPt, East Hampton, NY
East Hampton
9.0 out of 10, Wonderful, (2 reviews)
"Absolutely Beautiful view The vibe and food was great. Just beware of the tics."
United States
Christina V.
$284 nightly
The price is $324
Aug 20 - Aug 21
Total with taxes and fees
Safari Tent Glamping,S10-CedarPt, East Hampton, NY

10. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (52 reviews)
"We enjoyed our stay"
United States
JM B.
$197 nightly
The price is $222
Sep 15 - Sep 16
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.

11. Safari Tent Glamping,S7-CedarPt, East Hampton, NY

Safari Tent Glamping,S7-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (1 review)
"Thank you Cedar Point for the great accommodations. We were fortunate to have a Tent right on the Bay, great views and good times."
United States
Vasilios
$259 nightly
The price is $296
Aug 18 - Aug 19
Total with taxes and fees
Safari Tent Glamping,S7-CedarPt, East Hampton, NY

12. Insta-worthy Couples Retreat: Perfect for romantic getaway!

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (60 reviews)
"A beautiful little beach cottage that was just what the doctor ordered. A great place to unwind and take in the sea air."
United States
Emily M.
$270 nightly
The price is $305
Sep 15 - Sep 16
Total with taxes and fees
Insta-worthy Couples Retreat: Perfect for romantic getaway!

13. The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise
Old Lyme
9.0 out of 10, Wonderful, (4 reviews)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
$275 nightly
The price is $310
Sep 14 - Sep 15
Total with taxes and fees
The Stern at Soundview · Beach+Ocean+Sunrise

14. The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Greenport
10.0 out of 10, Exceptional, (1 review)
"Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!"
United States
Jeannette M.
$995 nightly
The price is $1,137
Sep 9 - Sep 10
Total with taxes and fees
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

15. Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (246 reviews)
"Best value and bang for your buck in Montauk other than Wavecrest in Amagansett."
United States
William
$263 nightly
The price is $300
Sep 13 - Sep 14
Total with taxes and fees
Driftwood Resort

16. Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (322 reviews)
"Easy access to the beach. Perfect weather. Nicely furnished and updated rooms and bathrooms. The gym is tiny- not much equipment. The location is perfect for Montauk and Amagansett. The staff were very nice and hard working."
United States
Gaurang J
$265 nightly
The price is $303
Sep 14 - Sep 15
Total with taxes and fees
Windward Shores Ocean Resort

17. Safari Tent Glamping,D28-CedarPt, East Hampton, NY

Safari Tent Glamping,D28-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (4 reviews)
"First time glamping with my boys and had a great time."
United States
Massimo P.
$270 nightly
The price is $309
Aug 19 - Aug 20
Total with taxes and fees
Safari Tent Glamping,D28-CedarPt, East Hampton, NY

18. Seabreeze #3 Cozy Cottage steps to the beach

Seabreeze #3 Cozy Cottage steps to the beach
Hampton Bays
10.0 out of 10, Exceptional, (1 review)
$532 nightly
The price is $571
Aug 19 - Aug 20
Total with taxes and fees
Seabreeze #3 Cozy Cottage steps to the beach

19. Safari Tent Glamping,S3-CedarPt, East Hampton, NY

Safari Tent Glamping,S3-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (3 reviews)
"The store was great and the upgrades were perfect. The pizza was excellent and hope to be back soon"
United States
Joseph
$284 nightly
The price is $324
Aug 20 - Aug 21
Total with taxes and fees
Safari Tent Glamping,S3-CedarPt, East Hampton, NY

20. Work and Play Special! Extended Stay Discount

Work and Play Special! Extended Stay Discount
Shelter Island
10.0 out of 10, Exceptional, (57 reviews)
"Really great property, had a relaxing lovely time!"
United States
Nava S.
$1,188 nightly
The price is $1,358
Sep 16 - Sep 17
Total with taxes and fees
Work and Play Special! Extended Stay Discount
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.
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Top Dering Harbor Hotel Reviews

Find out more about Dering Harbor

Everything you need to know about Dering Harbor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Dering Harbor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Dering Harbor vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Dering Harbor vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Dering Harbor. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Dering Harbor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $222 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Dering Harbor rentals

At Expedia, we put the best Dering Harbor vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Dering Harbor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Dering Harbor vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Dering Harbor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find vacation rentals in Dering Harbor?

Yes, we give you a choice of vacation rentals near popular attractions in Dering Harbor, or you can select a more secluded option if you want a relaxing place to stay.

What are some of the best vacation home rentals in Dering Harbor?

The Hampton Sack a cheerful relaxing beach cottage: This vacation home rental outside of Dering Harbor is equipped with a barbecue grill, air-conditioning, and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

What can I see and do in Dering Harbor?

While exploring the area, visit family-friendly sights like Railroad Museum of Long Island, or get outside and enjoy nature at Sunset Beach. In the larger area, you’ll find Greenport Carousel and Kontokosta Winery.

What are vacation rentals like in Dering Harbor?

Vacation rentals are private accommodations you can book for a couple days or more in Dering Harbor. Vacation rentals provide amenities such as laundry facilities and kitchens so you'll have everything you want. If you're concerned about a sanitized environment, vacation rentals can offer a sense of privacy away from shared hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for small groups.