Default HTG hotel image

Dering Harbor Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Dering Harbor holiday rentals

1. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (289 reviews)
"Great place!"
United States
Christine
The price is NZ$734
includes taxes & fees
21 Sept - 22 Sept
Cliffside Resort Condominiums

2. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (51 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
The price is NZ$582
includes taxes & fees
13 Sept - 14 Sept
North Fork Resort

3. Harbor Heights

Harbor Heights
Pipes Cove
10.0 out of 10, Exceptional, (23 reviews)
"Close to the train, beach and restaurant, very convenient on foot"
United States
Nigel
The price is NZ$586
includes taxes & fees
3 Sept - 4 Sept
Harbor Heights

4. 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, (29 reviews)
"We had a great stay!! "
United States
Callie E.
The price is NZ$705
includes taxes & fees
7 Sept - 8 Sept
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

5. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (50 reviews)
"access"
United States
Timothy
The price is NZ$590
includes taxes & fees
10 Sept - 11 Sept
The SandPiper

6. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (42 reviews)
"Such a wonderful stay! Christopher was such a great host, the property matched the description, was extremely clean and situated in a perfect location just a short walk from town! Would stay again & recommend to family/friends!"
United States
Anonymous traveller
The price is NZ$628
includes taxes & fees
8 Sept - 9 Sept
Aqua Vista

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.
The price is NZ$725
includes taxes & fees
1 Sept - 2 Sept
American Beech in Greenport - Petite King Room 7

8. Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, Exceptional, (10 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$695
includes taxes & fees
14 Sept - 15 Sept
Beach Block Hideaway

9. Renovated Townhouse walk to all

Renovated Townhouse walk to all
Greenport
9.4 out of 10, Exceptional, (12 reviews)
"We had a wonderful girls weekend in Greenport. The house was perfect for the three of us. Loved the location. We didn’t get to use the back area due to the weather, but it looked so inviting. Next time!"
United States
Melissa A.
The price is NZ$1,241
includes taxes & fees
17 Sept - 18 Sept
Renovated Townhouse walk to all

10. 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.
The price is NZ$494
includes taxes & fees
30 Aug - 31 Aug
Safari Tent Glamping,S10-CedarPt, East Hampton, NY

11. Safari Tent Glamping,S4-CedarPt, East Hampton, NY

Safari Tent Glamping,S4-CedarPt, East Hampton, NY
East Hampton
The price is NZ$497
includes taxes & fees
30 Aug - 31 Aug
Safari Tent Glamping,S4-CedarPt, East Hampton, NY

12. 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$1,854
includes taxes & fees
15 Sept - 16 Sept
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

13. Northfork Townhouse walk to all

Northfork Townhouse walk to all
Greenport
10.0 out of 10, Exceptional, (7 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$1,578
includes taxes & fees
17 Sept - 18 Sept
Northfork Townhouse walk to all

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

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (53 reviews)
"We enjoyed our stay"
United States
JM B.
The price is NZ$395
includes taxes & fees
30 Aug - 31 Aug
1-bedroom cottage with Grove Beach 🏖️ access.

15. American Beech in Greenport - Deluxe King 6

American Beech in Greenport - Deluxe King 6
Greenport
2.0 out of 10, (1 review)
"Not as advertised. Very disappointed "
United States
Jeffrey
The price is NZ$789
includes taxes & fees
31 Aug - 1 Sept
American Beech in Greenport - Deluxe King 6

16. 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
The price is NZ$477
includes taxes & fees
2 Sept - 3 Sept
The Stern at Soundview · Beach+Ocean+Sunrise

17. Charming Accommodations in the Hamptons

Charming Accommodations in the Hamptons
Sag Harbor
The price is NZ$865
includes taxes & fees
7 Sept - 8 Sept
Charming Accommodations in the Hamptons

18. Safari Tent Glamping,S2-CedarPt, East Hampton, NY

Safari Tent Glamping,S2-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (1 review)
"Comfortable bed and beautiful surroundings"
United States
Matthew
The price is NZ$541
includes taxes & fees
1 Sept - 2 Sept
Safari Tent Glamping,S2-CedarPt, East Hampton, NY

19. The gardners Cottage 1 mile from long Island Sound - pet friendly

The gardners Cottage 1 mile from long Island Sound - pet friendly
Clinton
9.8 out of 10, Exceptional, (28 reviews)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
The price is NZ$540
includes taxes & fees
1 Sept - 2 Sept
The gardners Cottage 1 mile from long Island Sound - pet friendly

20. Safari Tent Glamping,D27-CedarPt, East Hampton, NY

Safari Tent Glamping,D27-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (4 reviews)
"great"
United States
Fiona B.
The price is NZ$519
includes taxes & fees
31 Aug - 1 Sept
Safari Tent Glamping,D27-CedarPt, East Hampton, NY
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

Top Dering Harbor Hotel Reviews

Find out more about Dering Harbor

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Dering Harbor holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Dering Harbor. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Dering Harbor. Seeing all the best attractions is bound to make you fall in love with Dering Harbor. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Dering Harbor short-term rentals, that won’t be hard to do.

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?

The Hampton Sack a cheerful relaxing beach cottage: This holiday home rental outside of Dering Harbor is equipped with a BBQ, 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 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.