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Dering Harbor Holiday Rentals

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Dering Harbor holiday rentals

Flat-screen TV

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
The price is HK$2,520
HK$2,880 total
includes taxes & fees
7 Sept - 8 Sept
North Fork Resort
Terrace/patio

2. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (284 reviews)
"Great place!"
United States
Christine
The price is HK$2,404
HK$3,446 total
includes taxes & fees
7 Sept - 8 Sept
Cliffside Resort Condominiums
Sun-loungers, beach towels

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.
The price is HK$1,530
HK$2,950 total
includes taxes & fees
10 Sept - 11 Sept
The SandPiper
Sun-loungers, beach towels

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.
The price is HK$1,530
HK$3,020 total
includes taxes & fees
15 Sept - 16 Sept
Aqua Vista
Beach

5. 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 HK$1,530
HK$3,021 total
includes taxes & fees
13 Sept - 14 Sept
Harbor Heights
Sun-loungers, beach towels

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.
The price is HK$1,923
HK$4,025 total
includes taxes & fees
7 Sept - 8 Sept
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
Terrace/patio

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 HK$2,424
HK$3,522 total
includes taxes & fees
13 Sept - 14 Sept
American Beech in Greenport - Petite King Room 7
Beach

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.
The price is HK$2,314
HK$4,302 total
includes taxes & fees
8 Sept - 9 Sept
Beach Block Hideaway
1 bedroom, bed sheets

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.
The price is HK$1,517
HK$2,325 total
includes taxes & fees
20 Aug - 21 Aug
Safari Tent Glamping,S10-CedarPt, East Hampton, NY
1 bedroom, desk, iron/ironing board, travel cot

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.
The price is HK$883
HK$1,743 total
includes taxes & fees
15 Sept - 16 Sept
1-bedroom cottage with Grove Beach 🏖️ access.
Property grounds

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
The price is HK$1,518
HK$2,326 total
includes taxes & fees
20 Aug - 21 Aug
Safari Tent Glamping,S7-CedarPt, East Hampton, NY
Beach nearby

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.
The price is HK$1,098
HK$2,423 total
includes taxes & fees
15 Sept - 16 Sept
Insta-worthy Couples Retreat: Perfect for romantic getaway!
Beach nearby

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
The price is HK$1,294
HK$2,433 total
includes taxes & fees
15 Sept - 16 Sept
The Stern at Soundview · Beach+Ocean+Sunrise
Smart TV, books

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.
The price is HK$5,807
HK$9,575 total
includes taxes & fees
9 Sept - 10 Sept
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Free WiFi, individually decorated, individually furnished, bed sheets

15. Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (247 reviews)
"Best value and bang for your buck in Montauk other than Wavecrest in Amagansett."
United States
William
The price is HK$1,837
HK$2,355 total
includes taxes & fees
13 Sept - 14 Sept
Driftwood Resort
Iron/ironing board, free WiFi, individually decorated

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
The price is HK$1,895
HK$2,378 total
includes taxes & fees
15 Sept - 16 Sept
Windward Shores Ocean Resort
Property grounds

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.
The price is HK$1,517
HK$2,424 total
includes taxes & fees
19 Aug - 20 Aug
Safari Tent Glamping,D28-CedarPt, East Hampton, NY
Smart TV, offices

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)
The price is HK$1,334
HK$4,407 total
includes taxes & fees
19 Aug - 20 Aug
Seabreeze #3 Cozy Cottage steps to the beach
Terrace/patio

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
The price is HK$1,517
HK$2,325 total
includes taxes & fees
20 Aug - 21 Aug
Safari Tent Glamping,S3-CedarPt, East Hampton, NY
Coffee/tea maker, fridge, microwave, oven

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.
The price is HK$5,911
HK$10,653 total
includes taxes & fees
16 Sept - 17 Sept
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

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

10/10 Excellent
"Very clean room beds very comfortable, All staff are very friendly and helpful Breakfast was great Just be on time!!!! Free parking an extra bonus Will definitely stay there again"
Patricia 3-night trip
Posted 1 hour ago
Quality Inn Old Saybrook - Westbrook

Find out more about Dering Harbor

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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 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.