Dering Harbor Vacation Rentals from $178: Search Short-Term Rentals

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Our top choices for Dering Harbor vacation rentals

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

1. North Fork Resort

Greenport

Altynai

$296 nightly

Nov 1 - Nov 2

Total with taxes and fees

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

2. Cliffside Resort Condominiums

Greenport

William

$266 nightly

Nov 12 - Nov 13

Total with taxes and fees

A beach with people relaxing on chairs and sunbathing.

3. Harbor Heights

Pipes Cove

Steven R.

$213 nightly

Nov 3 - Nov 4

Total with taxes and fees

A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

4. Aqua Vista

Pipes Cove

Kerri L.

$223 nightly

Nov 9 - Nov 10

Total with taxes and fees

A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

5. The SandPiper

Pipes Cove

Manuela C.

$213 nightly

Nov 10 - Nov 11

Total with taxes and fees

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

Pipes Cove

Callie E.

$321 nightly

Nov 2 - Nov 3

Total with taxes and fees

An outdoor dining area with hanging lights, palm trees, and a bar.

7. American Beech in Greenport - Petite King Room 7

Greenport

Paul F.

$266 nightly

Nov 1 - Nov 2

Total with taxes and fees

A wooden pathway leading to a beach with scattered rocks and greenery.

8. Beach Block Hideaway

Pipes Cove

Teresa C.

$394 nightly

Nov 3 - Nov 4

Total with taxes and fees

A modern living room with a sofa, coffee table, and dining area.

9. The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

Greenport

Jeannette M.

$776 nightly

Nov 11 - Nov 12

Total with taxes and fees

A wooden deck with lounge chairs and a potted plant, overlooking a beach and ocean.

10. Beachfront Greenport Villa

Greenport

Kate R.

$924 nightly

Nov 11 - Nov 12

Total with taxes and fees

11. Driftwood Resort

Montauk

Julian

$166 nightly

Oct 30 - Oct 31

Total with taxes and fees

12. Windward Shores Ocean Resort

Napeague

Banessa

$156 nightly

Nov 12 - Nov 13

Total with taxes and fees

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.

13. Renovated Townhouse walk to all

Greenport

Liz H.

$504 nightly

Nov 16 - Nov 17

Total with taxes and fees

A modern dining area with a wooden table, white chairs, and a chandelier.

14. Northfork Townhouse walk to all

Greenport

Beth R.

$504 nightly

Nov 10 - Nov 11

Total with taxes and fees

A backyard with a swimming pool, wicker lounge chairs, and potted plants.

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

Sag Harbor

maria m.

$985 nightly

Oct 30 - Oct 31

Total with taxes and fees

A modern kitchen with a stainless steel refrigerator, white cabinets, a window with a view, and a chandelier.

16. Charming Accommodations in the Hamptons

Sag Harbor

$446 nightly

Nov 2 - Nov 3

Total with taxes and fees

A bedroom with a wooden bed, bedside lamps, a sofa, and a TV stand.

17. 1-bedroom cottage with Grove Beach 🏖️ access.

Clinton

JM B.

$251 nightly

Nov 1 - Nov 2

Total with taxes and fees

A modern living room with a wooden accent wall, a flat-screen TV, a fireplace, and a dining area with a chair and table.

18. Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.

Bridgehampton

Katie B.

$514 nightly

Nov 8 - Nov 9

Total with taxes and fees

A living room with a fireplace, a sofa, a coffee table, and a cabinet.

19. Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

Old Saybrook

Karol T.

$403 nightly

Nov 3 - Nov 4

Total with taxes and fees

A rocky shoreline with a beach and ocean in the background.

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

Old Lyme

"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."

Janine

$237 nightly

Nov 2 - Nov 3

Total with taxes and fees

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Top Dering Harbor Hotel Reviews

The Harbor Front Inn

10/10 Excellent

"Such a lovely place for a getaway. Charming town and lovely water views!"

Zey Hotel

10/10 Excellent

"The stay was perfect. I can't think of a single thing to criticize. As an example, when we were checking out, we called the manager on his cell to alert him that a fire truck was flushing the street hydrants, and that we noticed that the water in the room was brown. We knew that the maintenance of the hydrants was causing the dirty water. The manager promptly told us we could stay until 6:00 pm for free, so that we would be able to take clean showers. We told him that we had showered early, and that we had no problem. But his response showed how he cared for the guests."

Faraway Sag Harbor

8/10 Good

"Beautiful and charming hotel! Unfortunately the restaurant was only serving breakfast and not dinner, since we arrived off- season. However the restaurant was freezing due to the heating system not working so we had to go elsewhere in town for breakfast. Too bad because it was a lovely room with a harbor view. Our biggest disappointment by far was the coffee in the room and in the lobby. Nasty stuff! I have never tasted coffee this bad in any hotel (and we have been to many). First of all at this high- end price point per night, Faraway should be providing at least a Nespresso machine in each room for a decent morning cup of coffee instead of instant coffee packets which went out with Sanka like forty years ago. :( Then we thought that maybe the coffee urns on the bar in the common area would at least provide a half decent cup of coffee. Boy were we wrong! The fact that other filled cups of coffee which were left on the bar still full told us that other guests felt the same about the quality of coffee. Thank goodness for Goldbergs Bagel shop in town! Come on guys. If you want to be recognized as a high end getaway in an extremely wealthy part of Long Island, please find yourselves a better quality coffee source. Its not that hard these days. We speak for all true coffee lovers."

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 $178 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.

Room 1

Check prices for these dates

Our top choices for Dering Harbor vacation rentals

1. North Fork Resort

2. Cliffside Resort Condominiums

3. Harbor Heights

4. Aqua Vista

5. The SandPiper

6. Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

7. American Beech in Greenport - Petite King Room 7

8. Beach Block Hideaway

9. The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

10. Beachfront Greenport Villa

11. Driftwood Resort

12. Windward Shores Ocean Resort

13. Renovated Townhouse walk to all

14. Northfork Townhouse walk to all

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

16. Charming Accommodations in the Hamptons

17. 1-bedroom cottage with Grove Beach 🏖️ access.

18. Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.

19. Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

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

Find vacation rentals that suit your style

Top Dering Harbor Hotel Reviews

The Harbor Front Inn

Silver Sands Motel & Beach Bungalows

Saybrook Point Resort & Marina

Zey Hotel

The Sagaponack

Ocean Vista Resort

Faraway Sag Harbor

Sag Harbor Inn

The Atlantic Hotel

Find out more about Dering Harbor

Frequently asked questions