Dering Harbor Holiday Rentals

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Holiday Rentals in Dering Harbor

Cliffside Resort Condominiums

3.0 star property
Greenport
9.0 out of 10, Wonderful, (248)
"Great stay - beautiful place"
United States
Rebecca
Cliffside Resort Condominiums

Large Charming Historic House close to Beaches

Clinton
9.8 out of 10, Exceptional, (34)
"Great place and location. There was 8 of us and plenty of space and beds!"
United States
Sandy B.
Large Charming Historic House close to Beaches

1-bedroom cottage with Grove Beach 🏖️ access.

Clinton
9.2 out of 10, Wonderful, (36)
"Cottage itself clean, but sewage smell in bathroom. Surrounding property derelict motel with ongoing consruction. "
United States
michelle
The price is NZ$317
includes taxes & fees
1 Dec - 2 Dec
1-bedroom cottage with Grove Beach 🏖️ access.

Driftwood Resort

3.5 star property
Montauk
9.0 out of 10, Wonderful, (236)
"Great place to stay for small family "
United States
DongHo
Driftwood Resort

Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

East Hampton
10.0 out of 10, Exceptional, (95)
"Awesome location. Very comfortable stay. Had everything we needed. Would definitely stay here again"
United States
Irish T.
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn

Madison
10.0 out of 10, Exceptional, (36)
"We had a wonderful time here!! "
United States
Leslie S.
The price is NZ$486
includes taxes & fees
18 Nov - 19 Nov
Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn

Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

Hampton Bays
9.6 out of 10, Exceptional, (143)
"Perfect property to hangout and stay entertained for hours"
United States
Ryder I.
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

Stunning Hampton Holiday Family Fantasy for your Team

East Hampton
9.8 out of 10, Exceptional, (74)
"We had an incredible stay! The property was as advertised. Very easy in and out and stocked with all the essentials to cook, hangout, use the pool or have a movie night. Our host was very responsive throughout the weekend and gave great recommendations. Highly recommend. "
United States
Henry S.
Stunning Hampton Holiday Family Fantasy for your Team

Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available

Sag Harbor
10.0 out of 10, Exceptional, (89)
"House that has everything you need for a wonderful getaway! Excellent communication with the property owner. Thank you Jay for everything and your hospitality! "
United States
Maria R.
Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available

Waterfront Beach House

Clinton
9.6 out of 10, Exceptional, (54)
"My sisters and I rented this for just a weekend getaway absolutely loved it. Plan to go back next year."
United States
Maria D.
Waterfront Beach House

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

Southampton
9.8 out of 10, Exceptional, (32)
"This place was so nice and so close to so many fun places! "
United States
Daniella L.
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

Waterfront Escape- 3BR Coastal Cottage w/ Boat Launch & Near Niantic Main Street

Waterford
10.0 out of 10, Exceptional, (1)
"The home was immaculate and updated with everything you could possibly want. Wonderful location and a great host!"
United States
Brian V.
Waterfront Escape- 3BR Coastal Cottage w/ Boat Launch & Near Niantic Main Street

Shoreline Oasis

Clinton
9.2 out of 10, Wonderful, (7)
"Everything was as advertised or better. Lovely quiet area near beautiful beaches and great restaurants. We had a terrific experience. "
United States
Tom S.
The price is NZ$459
includes taxes & fees
18 Nov - 19 Nov
Shoreline Oasis

The Stern at Soundview · Beach+Ocean+Sunrise

2.0 star property
Old Lyme
10.0 out of 10, Exceptional, (3)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
The price is NZ$342
includes taxes & fees
18 Nov - 19 Nov
The Stern at Soundview · Beach+Ocean+Sunrise

Adorable Cottage, 5 min walk to water & town

Westbrook Center
9.4 out of 10, Exceptional, (14)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
The price is NZ$886
includes taxes & fees
30 Nov - 1 Dec
Adorable Cottage, 5 min walk to water & town

Charming 4-bedroom house with salt water pool, AC and WiFi in Hampton Bays

Hampton Bays
10.0 out of 10, Exceptional, (1)
"Awesome house, very convenient to the beach and town. Beautiful yard and pool for grilling and hanging. Would love to come back again!"
United States
Brendan O.
Charming 4-bedroom house with salt water pool, AC and WiFi in Hampton Bays

Beach House

East Lyme
9.6 out of 10, Exceptional, (57)
"Loved property. Great location, great yard, so easy to relax."
United States
Nicole M.
Beach House

STUNNING LUXURY HOME ~ PRIVATE POOL/HOT TUB ~ PERFECT HAMPTONS GETAWAY ~ MBH

East Hampton
9.6 out of 10, Exceptional, (39)
"We came for a long weekend to celebrate a big birthday. The house is wonderful and has everything you need. Michael was highly responsive when we had questions or could not find things. Beautiful outdoor areas too. Close to the beach. "
United States
Masha T.
STUNNING LUXURY HOME ~ PRIVATE POOL/HOT TUB ~ PERFECT HAMPTONS GETAWAY ~ MBH

Newly Renovated, Stylish Peconic Retreat with Private Pool, Lush Grounds,...

Peconic
10.0 out of 10, Exceptional, (2)
"This was a perfect home base for our 40th birthday weekend. Great space and location. The home was exactly as pictured. "
United States
jen k.
Newly Renovated, Stylish Peconic Retreat with Private Pool, Lush Grounds,...

The Bridge at Soundview · Beach+OceanView+Sunrise

2.0 star property
Old Lyme
10.0 out of 10, Exceptional, (1)
"The space was much larger than expected and was perfect for a group of 4 adults and 3 kids under 3! We had a great time, being a 5 minute walk from the beach and having a comfortable space to come back to. We'll definitely be coming back."
United States
Emotional J.
The price is NZ$858
includes taxes & fees
19 Nov - 20 Nov
The Bridge at Soundview · Beach+OceanView+Sunrise
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 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$317 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?

Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available : This holiday home rental outside of Dering Harbor is located near the beach, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

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 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.