Dering Harbor Holiday Rentals

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Holiday Rentals in Dering Harbor

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (288)
"Easy checking in and out Easy access few steps to beach from first floor unit "
The price is NZ$667
includes taxes & fees
9 July - 10 July
Windward Shores Ocean Resort

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (226)
"Very nice, clean and cosy place! Highly recommend!"
The price is NZ$494
includes taxes & fees
9 July - 10 July
Cliffside Resort Condominiums

Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill

8.6 out of 10, Excellent, (25)
"This adorable, cozy cottage was perfect for our family getaway to Montauk. We have tried various rentals and hotels each summer and Robert’s cottage was by far our favorite. It fit our family of 5 perfectly, with enough room that we didn’t feel on top of each other. The decor was light and airy and just what we were hoping to find. From the awesome location, just a walk to the ocean, to the indoor pool and back up to a comfortable stay, our entire family agree that we can’t wait to return!...
Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill

Driftwood Resort

3.5 star property
9.0 out of 10, Wonderful, (225)
"Phenomenal property and our room had a private sand patio. Service was extremely attentive and friendly. The beach was very spacious and pretty clean."
The price is NZ$668
includes taxes & fees
9 July - 10 July
Driftwood Resort

Canoe Place Waterfront Residences

4.0 star property
Canoe Place Waterfront Residences

Fairy Tale Guest Cottage in Magic Garden by Pool

10.0 out of 10, Exceptional, (68)
"We had a wonderful vacation at the Fairy Tale Guest Cottage. The location was awesome and we loved the accommodations, especially the fancy bathroom. Mark and Eunyoung are impeccable hosts. Would absolutely stay again!"
Fairy Tale Guest Cottage in Magic Garden by Pool

Escape to Sag Harbor

10.0 out of 10, Exceptional, (47)
"Amazing house and location!! Would stay again "
Escape to Sag Harbor

Hamptons Retreat

Hamptons Retreat

Perfect Mid-Century Private Waterfront East Hampton Retreat!

10.0 out of 10, Exceptional, (79)
"Very nice and relaxing stay in Springs! "
Perfect Mid-Century Private Waterfront East Hampton Retreat!

Shoreline Oasis

6.0 out of 10, (1)
"So the listing said house number 26 but it's really 25. So we circled the block a few times. Then the key was not in the key safe. Called the owner who apologized profusely. Had to wait a half hour for the key. Not ideal. Otherwise ok. "
The price is NZ$430
includes taxes & fees
9 July - 10 July
Shoreline Oasis

East Hampton- Beautiful 4 Bedroom Home, Large Heated Pool, Private Backyard

10.0 out of 10, Exceptional, (75)
"Stayed here over Thanksgiving. Beautiful house, well appointed, great location. The Hamptons at Thanksgiving are very vibrant. Highly recommend a stay here. "
East Hampton- Beautiful 4 Bedroom Home, Large Heated Pool, Private Backyard

Driftwood Cottage by RoveTravel| 3BR Quiet Cottage

9.4 out of 10, Exceptional, (10)
"I stayed here with family recently and loved the house. The location was private and convenient. The management company was available to answer our questions. It was perfect for an off season get away. "
Driftwood Cottage by RoveTravel| 3BR Quiet Cottage

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

10.0 out of 10, Exceptional, (87)
"Beautiful house with lots of light and comfort. Excellent quiet location by the ocean with outstanding communication with the host who answered all pertinent questions and addressed all outstanding issues. "
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

Heated pool/5 min walk to Beach/Beautiful Sag Harbor Village /Restaurant/Museum

10.0 out of 10, Exceptional, (45)
"Great house, kitchen is well equipped which made dining in very easy. Loved the pool and backyard."
Heated pool/5 min walk to Beach/Beautiful Sag Harbor Village /Restaurant/Museum

Private Beach Community in East Hampton! Pool, HotTub, Trampoline & Pirate Ship!

10.0 out of 10, Exceptional, (85)
"It was a great stay"
Private Beach Community in East Hampton! Pool, HotTub, Trampoline & Pirate Ship!

Charming 3-bedroom, 3 bath house in l Sag village, Harbor with pool, AC, WiFi

2.0 star property
8.0 out of 10, Very good, (6)
"We had a fantastic stay! The home was exactly as described — clean and very comfortable. The location was perfect. We loved being close to town. Communication was smooth and easy — Frank was quick to respond. We’d absolutely stay here again and recommend it to anyone visiting the area! "
The price is NZ$1,197
includes taxes & fees
5 Aug - 6 Aug
Charming 3-bedroom, 3 bath house in l Sag village, Harbor with pool, AC, WiFi

Charming East Hampton Home, private yard with fenced in pool, perfect for...

Charming East Hampton Home, private yard with fenced in pool, perfect for...

The Mast at Soundview · Beach+Ocean+Sunrise

2.0 star property
9.0 out of 10, Wonderful, (2)
"Nice place, little smaller than I was expecting, but location was close to the beach, info regarding access to the property was clear and easy to follow! Parking was assigned but other occupants decided not to utilize their assigned space and took ours. Be prepared to clean the studio before you leave to include dishes and take out the trash. Was surprised by the cleaning request. Overall great weekend!"
The price is NZ$336
includes taxes & fees
9 July - 10 July
The Mast at Soundview · Beach+Ocean+Sunrise

adorable ranch in beach community

10.0 out of 10, Exceptional, (45)
"Close to the shore and the heart of Old Saybrook. The house is very comfortable."
The price is NZ$1,066
includes taxes & fees
9 July - 10 July
adorable ranch in beach community

Southampton cozy cottage by the beach

The price is NZ$1,570
includes taxes & fees
27 July - 28 July
Southampton cozy cottage by the beach
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.
Save an average of 15% on thousands of hotels when you're signed in

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?

Escape to Sag Harbor: This holiday home rental outside of Dering Harbor offers an outdoor pool, a fireplace and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 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 pool table 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.