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Dering Harbor Vacation Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Dering Harbor vacation rentals

A balcony with a view of the ocean, a lawn, and a house in the background.

1. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (300 reviews)
"Great condo. Very nice location and grounds."
United States
William
The price is AED 706
AED 1,214 total
includes taxes & fees
26 Nov - 27 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, (73 reviews)
"Everything was perfect 💞"
United States
Altynai
The price is AED 1,145
AED 1,308 total
includes taxes & fees
23 Nov - 24 Nov
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, (29 reviews)
"Perfect spot to stay on the North Fork!"
United States
Steven R.
The price is AED 314
AED 837 total
includes taxes & fees
22 Nov - 23 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, (54 reviews)
"Great property and location. So easily walkable to everything. The host was super responsive, we had a great stay!"
United States
Carey D.
The price is AED 349
AED 881 total
includes taxes & fees
18 Nov - 19 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, (58 reviews)
"Place was perfect ! Great location / clean/ everything we needed was there ! Would love to stay there again :)"
United States
Manuela C.
The price is AED 349
AED 852 total
includes taxes & fees
30 Nov - 1 Dec
The SandPiper
A beach with people relaxing, a pier extending into the water, and a clear sky.

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, (35 reviews)
"We had a great stay!! "
United States
Callie E.
The price is AED 479
AED 1,278 total
includes taxes & fees
16 Nov - 17 Nov
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
An outdoor dining area with hanging lights, palm trees, and a bar.

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 AED 731
AED 1,058 total
includes taxes & fees
16 Nov - 17 Nov
American Beech in Greenport - Petite King Room 7
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 AED 716
AED 1,574 total
includes taxes & fees
16 Nov - 17 Nov
Beach Block Hideaway
Room

9. Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (334 reviews)
"Omg so peaceful and beautiful. Felt like I was in paradise. My fiancee and I enjoyed every moment except checking out because we did not want to leave. Such beauty it was worth the 3 hour car ride. Perfect getaway.💜🙏"
United States
Banessa
The price is AED 484
AED 653 total
includes taxes & fees
16 Nov - 17 Nov
Windward Shores Ocean Resort
A modern dining area with a wooden table, white chairs, and a chandelier.

10. Northfork Townhouse walk to all

Northfork Townhouse walk to all
Greenport
9.4 out of 10, Exceptional, (9 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 AED 1,140
AED 2,352 total
includes taxes & fees
29 Nov - 30 Nov
Northfork Townhouse walk to all
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, (15 reviews)
"The place was as advertised and in great walking distance to everything in town! "
United States
Liz H.
The price is AED 1,058
AED 2,245 total
includes taxes & fees
29 Nov - 30 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 AED 826
AED 1,821 total
includes taxes & fees
14 Dec - 15 Dec
Charming Accommodations in the Hamptons
A house with a sliding glass door, a white door, and a small porch with potted plants.

13. Designer Sag Harbor Home w/ Pool + Fire Pit + Yard

Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
Sag Harbor
10.0 out of 10, Exceptional, (1 review)
"excellent and convenient stay!! located close into town, perfect for the small family group I was traveling with. home was very clean, cozy, had everything we needed! backyard with pool was a dream, beautifully landscaped, plenty of seating, very clean pool, would stay again! thanks for a delightful escape!"
United States
maria m.
The price is AED 1,066
AED 2,233 total
includes taxes & fees
16 Nov - 17 Nov
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
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
9.8 out of 10, Exceptional, (67 reviews)
"Cozy vrbo with a great location to the beach, outlets shops and excellent restaurants!"
United States
Marcy C.
The price is AED 554
AED 930 total
includes taxes & fees
19 Nov - 20 Nov
1-bedroom cottage with Grove Beach 🏖️ access.
A Keurig coffee maker, a tray with various coffee pods, and a paper towel dispenser.

15. 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 AED 422
AED 863 total
includes taxes & fees
16 Nov - 17 Nov
The Stern at Soundview · Beach+Ocean+Sunrise
A modern living room with a sofa, coffee table, and dining area.

16. 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 AED 1,737
AED 3,068 total
includes taxes & fees
1 Dec - 2 Dec
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
A kitchen with a wooden countertop, a black sink, and a window with a view of trees.

17. North Fork Grinch Getaway & Hot Chocolate Bar. Two Bedroom Sleeps 4.

North Fork Grinch Getaway & Hot Chocolate Bar. Two Bedroom Sleeps 4.
Southold
9.6 out of 10, Exceptional, (10 reviews)
"Beautiful property, comfortable and very clean!"
United States
Doran R.
The price is AED 918
AED 1,737 total
includes taxes & fees
23 Nov - 24 Nov
North Fork Grinch Getaway & Hot Chocolate Bar. Two Bedroom Sleeps 4.
A beach with waves, a clear sky, and a sandy shore.

18. Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included

Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
Westbrook Center
10.0 out of 10, Exceptional, (1 review)
"Able to walk to all the nearby restaurants with this location, including the beach. Very clean rooms with 2 TVs and controllable AC. Would definitely visit here again."
United States
Mason T.
The price is AED 360
AED 1,027 total
includes taxes & fees
16 Nov - 17 Nov
Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
An outdoor seating area with wicker furniture, a fire feature, and glasses of red wine.

19. 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 AED 878
AED 1,251 total
includes taxes & fees
16 Nov - 17 Nov
American Beech in Greenport - Deluxe King 6
A cozy living room with a sofa, a coffee table, and a dining area with chairs.

20. NEW private studio 1.1 miles to beach in East Lyme

NEW private studio 1.1 miles to beach in East Lyme
East Lyme
10.0 out of 10, Exceptional, (1 review)
"Very clean!"
United States
Agatha C.
The price is AED 514
AED 686 total
includes taxes & fees
16 Nov - 17 Nov
NEW private studio 1.1 miles to beach in East Lyme
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

8/10 Good
"The location of this hotel was excellent. It is close to many restaurants. Easy to get an Uber/Lyft. The clerk at the reception was knowledgeable and friendly. The room was clean. The breakfast was good. The hotel needs some updating which they are in the process of doing and that is why I gave it 4 stars overall."
Kerry 1-night trip
Posted 1 day ago
Quality Inn Old Saybrook - Westbrook

Frequently asked questions

Can I find vacation rentals in Dering Harbor?

Yes, we give you a choice of vacation rentals near popular attractions in Dering Harbor, or you can select a more secluded option if you want a relaxing place to stay.

What are some of the best vacation home rentals in Dering Harbor?

Bayfront 5 bedrooms family home. Panoramic sea view from all rooms: This vacation home rental outside of Dering Harbor is located by the ocean and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation 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 larger area, you’ll find Greenport Carousel and Kontokosta Winery.

What are vacation rentals like in Dering Harbor?

Vacation rentals are private accommodations you can book for a couple days or more in Dering Harbor. Vacation rentals provide amenities such as laundry facilities and kitchens so you'll have everything you want. If you're concerned about a sanitized environment, vacation rentals can offer a sense of privacy away from shared hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for small groups.