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Dering Harbor Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Dering Harbor holiday rentals

Terrace/patio

1. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (297 reviews)
"Great condo. Very nice location and grounds."
United States
William
The price is NZ$542
includes taxes & fees
1 Nov - 2 Nov
Cliffside Resort Condominiums
A modern house with a deck, outdoor seating, and a fire pit.

2. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (65 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
United States
Harold
The price is NZ$494
includes taxes & fees
18 Oct - 19 Oct
North Fork Resort
A beach with people relaxing on chairs and sunbathing.

3. Harbor Heights

Harbor Heights
Pipes Cove
10.0 out of 10, Exceptional, (27 reviews)
"Perfect spot to stay on the North Fork!"
United States
Steven R.
The price is NZ$440
includes taxes & fees
1 Nov - 2 Nov
Harbor Heights
A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

4. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (50 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is NZ$438
includes taxes & fees
9 Nov - 10 Nov
Aqua Vista
A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

5. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (55 reviews)
"Very wonderful location so close to the train station will come back soon"
United States
Julian V.
The price is NZ$438
includes taxes & fees
10 Nov - 11 Nov
The SandPiper
An outdoor dining area with hanging lights, palm trees, and a bar.

6. 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.
The price is NZ$533
includes taxes & fees
15 Oct - 16 Oct
American Beech in Greenport - Petite King Room 7
A beach with people relaxing, a pier extending into the water, and a clear sky.

7. 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, (34 reviews)
"We had a wonderful stay in Greenport! The location was absolutely perfect, and one of the things we loved most was being able to walk to town and the beautiful harbor. Everything was so conveniently located, from the charming shops and wonderful restaurants to the lovely waterfront, making it easy to enjoy everything Greenport has to offer without needing to drive. We would happily stay here again and highly recommend this place to anyone looking for a wonderful Greenport getaway!"
United States
Nino
The price is NZ$668
includes taxes & fees
9 Nov - 10 Nov
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
A wooden pathway leading to a beach with scattered rocks and greenery.

8. Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful 2 bedroom close to town. The house is well kept we would rent here again."
United States
Teresa C.
The price is NZ$794
includes taxes & fees
9 Nov - 10 Nov
Beach Block Hideaway
A modern dining area with a wooden table, white chairs, and a chandelier.

9. Northfork Townhouse walk to all

Northfork Townhouse walk to all
Greenport
9.4 out of 10, Exceptional, (8 reviews)
"Great property located in a quiet neighborhood within walking distance to all in Greenport. The townhouse was clean and kitchen was well- appointed with off the street parking. Playground up the street was an added bonus with a old school merry-go-round! Would definitely stay again"
United States
Beth R.
The price is NZ$973
includes taxes & fees
10 Nov - 11 Nov
Northfork Townhouse walk to all
Room

10. Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (326 reviews)
"The room was nice but the bed was horrible. They need to replace the bed ASAP. It is so old that the middle of the bed is touching the floor due to it being worn out. Our backs are still hurting. Otherwise it was a nice room."
United States
William
The price is NZ$339
includes taxes & fees
15 Oct - 16 Oct
Windward Shores Ocean Resort
A living room with a fireplace, a television mounted above it, a dining area with a table and chairs, and a staircase with wooden railings.

11. Renovated Townhouse walk to all

Renovated Townhouse walk to all
Greenport
9.6 out of 10, Exceptional, (14 reviews)
"The place was as advertised and in great walking distance to everything in town! "
United States
Liz H.
The price is NZ$1,052
includes taxes & fees
10 Nov - 11 Nov
Renovated Townhouse walk to all
A modern kitchen with a stainless steel refrigerator, white cabinets, a window with a view, and a chandelier.

12. Charming Accommodations in the Hamptons

Charming Accommodations in the Hamptons
Sag Harbor
The price is NZ$871
includes taxes & fees
20 Oct - 21 Oct
Charming Accommodations in the Hamptons
A modern living room with a sofa, coffee table, and dining area.

13. 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.
The price is NZ$1,653
includes taxes & fees
2 Nov - 3 Nov
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
A bedroom with a wooden bed, bedside lamps, a sofa, and a TV stand.

14. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (61 reviews)
"We enjoyed our stay"
United States
JM B.
The price is NZ$370
includes taxes & fees
21 Oct - 22 Oct
1-bedroom cottage with Grove Beach 🏖️ access.
A dining area with a round table, six chairs, and a chandelier.

15. Year round Jacuzzi - Blackberry East Hampton Home

Year round Jacuzzi - Blackberry East Hampton Home
East Hampton
9.2 out of 10, Wonderful, (7 reviews)
"We had a great time staying here. The home is well worn and there are some fixtures that should be replaced "
United States
Suzanne R.
The price is NZ$2,194
includes taxes & fees
15 Oct - 16 Oct
Year round Jacuzzi - Blackberry East Hampton Home
Room

16. Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
8.8 out of 10, Excellent, (256 reviews)
"Great right on the beach property with nice pool."
United States
Julian
The price is NZ$337
includes taxes & fees
15 Oct - 16 Oct
Driftwood Resort
A modern kitchen with white cabinets, a microwave, and a large TV displaying a beach scene.

17. Adorable Cottage, 5 min walk to water & town

Adorable Cottage, 5 min walk to water & town
Westbrook Center
9.2 out of 10, Wonderful, (17 reviews)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
The price is NZ$798
includes taxes & fees
15 Oct - 16 Oct
Adorable Cottage, 5 min walk to water & town
A rocky shoreline with a beach and ocean in the background.

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

The Stern at Soundview · Beach+Ocean+Sunrise
Old Lyme
8.4 out of 10, Very good, (6 reviews)
"If you are looking for a place to sleep, this place is ok. No place to sit down or put anything down. Just a bed and an old beat up tiny side table. Refrigerator is tiny, needed to be cleaned and defrosted. Stains in the bathroom ceiling tiles and the smell of Marijuana at night. Hot plate and microwave present but did not use. The entryway and stairs were dirty and could use a coat of paint and trim. The beach was the highlight and a very short walk. Definitely not worth the $$$ we paid."
United States
Janine
The price is NZ$510
includes taxes & fees
15 Oct - 16 Oct
The Stern at Soundview · Beach+Ocean+Sunrise
A driveway with a parked car, surrounded by trees and illuminated pathway lights.

19. Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.

Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
Bridgehampton
10.0 out of 10, Exceptional, (1 review)
"We thoroughly enjoyed our stay. The property was exactly as described, very well maintained, comfortable, and welcoming. The location is ideal for exploring the Hamptons, with convenient access to Sag Harbor, East Hampton, and Bridgehampton. We would definitely recommend this property to others visiting the area."
United States
Robert R.
The price is NZ$1,024
includes taxes & fees
2 Nov - 3 Nov
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
A living room with a fireplace, a sofa, a coffee table, and a cabinet.

20. Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Old Saybrook
10.0 out of 10, Exceptional, (15 reviews)
"Very clean & comfortable home, great host & location! "
United States
Becky W.
The price is NZ$778
includes taxes & fees
18 Oct - 19 Oct
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
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

Zey Hotel

Zey Hotel

10/10 Excellent
"It worked out well for me."
Elizabeth 1-night trip
Posted 6 hours ago
Zey Hotel

Find out more about Dering Harbor

Everything you need to know about Dering Harbor holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Dering Harbor holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Dering Harbor holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Dering Harbor holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Dering Harbor holiday rentals we have selected for you start as low as NZ$337 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Dering Harbor rentals

At Expedia, we put the best Dering Harbor holiday 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 holiday.

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 holiday rentals in Dering Harbor?

Yes, there are holiday rentals close to the most popular sights in Dering Harbor, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Dering Harbor has to offer?

Bayfront 5 bedrooms family home. Panoramic sea view from all rooms: This holiday home rental outside of Dering Harbor is located by the ocean, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of books.

What can I see and do in Dering Harbor?

While exploring the area, visit family-friendly sights like East End Seaport Maritime Museum, or get outside and enjoy nature at Sunset Beach. In the wider area, you’ll find Greenport Carousel and Kontokosta Winery.

What are holiday rentals like in Dering Harbor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Dering Harbor. Holiday rentals offer extras like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from public hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for a small group gathering.