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Dering Harbor Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Dering Harbor vacation rentals

A modern house with a deck, outdoor seating, and a fire pit.

1. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (61 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
United States
Harold
$222 nightly
The price is $254
Oct 4 - Oct 5
Total with taxes and fees
North Fork Resort
Terrace/patio

2. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (295 reviews)
"Great place!"
United States
Christine
$266 nightly
The price is $304
Nov 1 - Nov 2
Total with taxes and fees
Cliffside Resort Condominiums
A beach with people relaxing on chairs and sunbathing.

3. Harbor Heights

Harbor Heights
Pipes Cove
10.0 out of 10, Exceptional, (26 reviews)
"Perfect spot to stay on the North Fork!"
United States
Steven R.
$222 nightly
The price is $254
Nov 1 - Nov 2
Total with taxes and fees
Harbor Heights
A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

4. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (52 reviews)
"Very wonderful location so close to the train station will come back soon"
United States
Julian V.
$280 nightly
The price is $320
Oct 18 - Oct 19
Total with taxes and fees
The SandPiper
A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

5. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (47 reviews)
"Great location and nice spot."
United States
Kerri L.
$222 nightly
The price is $254
Nov 1 - Nov 2
Total with taxes and fees
Aqua Vista
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, (32 reviews)
"We had a great stay!! "
United States
Callie E.
$336 nightly
The price is $384
Nov 1 - Nov 2
Total with taxes and fees
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.
$268 nightly
The price is $306
Oct 4 - Oct 5
Total with taxes and fees
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.
$452 nightly
The price is $516
Oct 4 - Oct 5
Total with taxes and fees
Beach Block Hideaway
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.

9. Renovated Townhouse walk to all

Renovated Townhouse walk to all
Greenport
9.6 out of 10, Exceptional, (14 reviews)
"The place was as advertised and in great walking distance to everything in town! "
United States
Liz H.
$571 nightly
The price is $652
Oct 26 - Oct 27
Total with taxes and fees
Renovated Townhouse walk to all
A modern living room with a sofa, coffee table, and dining area.

10. 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.
$838 nightly
The price is $957
Oct 7 - Oct 8
Total with taxes and fees
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Room

11. Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (324 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
$143 nightly
The price is $163
Oct 15 - Oct 16
Total with taxes and fees
Windward Shores Ocean Resort
A tent with a wooden frame, two red chairs, and a table.

12. 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.
$260 nightly
The price is $298
Oct 2 - Oct 3
Total with taxes and fees
Safari Tent Glamping,S10-CedarPt, East Hampton, NY
A rocky shoreline with a beach and ocean in the background.

13. The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise
Old Lyme
8.0 out of 10, Very good, (5 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
$257 nightly
The price is $291
Oct 5 - Oct 6
Total with taxes and fees
The Stern at Soundview · Beach+Ocean+Sunrise
A modern dining area with a wooden table, white chairs, and a chandelier.

14. Northfork Townhouse walk to all

Northfork Townhouse walk to all
Greenport
9.4 out of 10, Exceptional, (8 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.
$608 nightly
The price is $694
Oct 20 - Oct 21
Total with taxes and fees
Northfork Townhouse walk to all
A modern kitchen with a stainless steel refrigerator, white cabinets, a window with a view, and a chandelier.

15. Charming Accommodations in the Hamptons

Charming Accommodations in the Hamptons
Sag Harbor
$446 nightly
The price is $510
Oct 5 - Oct 6
Total with taxes and fees
Charming Accommodations in the Hamptons
A bedroom with a wooden bed, bedside lamps, a sofa, and a TV stand.

16. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (60 reviews)
"We enjoyed our stay"
United States
JM B.
$202 nightly
The price is $229
Oct 26 - Oct 27
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.
A tented accommodation with two beds, a small table, a chair, and a cabinet.

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

Safari Tent Glamping,D27-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (5 reviews)
"We loved the idea of "roughing it" while still sleeping in a cozy bed. It was nice to expose my children to nature. We took a long walk on the beach. Cooked hotdogs and hamburgers on the grill and made s'mores on the campfire."
United States
Brian
$271 nightly
The price is $310
Oct 2 - Oct 3
Total with taxes and fees
Safari Tent Glamping,D27-CedarPt, East Hampton, NY
A stone pier leading to a beach with houses in the background.

18. Insta-worthy Couples Retreat: Perfect for romantic getaway!

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (61 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.
$245 nightly
The price is $277
Oct 8 - Oct 9
Total with taxes and fees
Insta-worthy Couples Retreat: Perfect for romantic getaway!
A beach with waves, a clear sky, and a sandy shore.

19. 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.
$291 nightly
The price is $331
Oct 7 - Oct 8
Total with taxes and fees
Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
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

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

8/10 Good
"The staff are very welcoming. A small point but the hot water in the bathroom is just warm and takes a time to arrive...."
David 2-night trip
Posted 16 hours ago
Saybrook Point Resort & Marina

Find out more about Dering Harbor

Everything you need to know about Dering Harbor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Dering Harbor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Dering Harbor vacation 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 low season months. For more hustle and bustle, you may prefer to visit Dering Harbor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $163 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Dering Harbor rentals

At Expedia, we put the best Dering Harbor vacation 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 vacation.

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 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.