Dering Harbor Vacation Rentals from ￥13,655: Search Short-Term Rentals

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Our top choices for Dering Harbor vacation rentals

1. Cliffside Resort Condominiums

Greenport

William

￥52,770 total

includes taxes & fees

Nov 26 - Nov 27

A rustic cabin with a wooden exterior, a front porch, and a staircase leading to the entrance.

2. North Fork Resort

Greenport

Altynai

￥56,868 total

includes taxes & fees

Nov 16 - Nov 17

A beach with people relaxing on chairs and sunbathing.

3. Harbor Heights

Pipes Cove

Steven R.

￥36,402 total

includes taxes & fees

Nov 22 - Nov 23

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

Carey D.

￥38,320 total

includes taxes & fees

Nov 18 - Nov 19

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

5. The SandPiper

Pipes Cove

Manuela C.

￥37,041 total

includes taxes & fees

Nov 30 - Dec 1

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.

￥55,561 total

includes taxes & fees

Nov 16 - Nov 17

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

7. American Beech in Greenport - Petite King Room 7

Greenport

Paul F.

￥45,983 total

includes taxes & fees

Nov 16 - Nov 17

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

8. Beach Block Hideaway

Pipes Cove

Teresa C.

￥68,424 total

includes taxes & fees

Nov 16 - Nov 17

9. Windward Shores Ocean Resort

Napeague

Banessa

￥28,384 total

includes taxes & fees

Nov 16 - Nov 17

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

10. Northfork Townhouse walk to all

Greenport

Beth R.

￥92,515 total

includes taxes & fees

Dec 1 - Dec 2

A modern kitchen with a marble island, pendant lights, and a patterned backsplash.

11. Renovated Townhouse walk to all

Greenport

Liz H.

￥85,488 total

includes taxes & fees

Nov 16 - Nov 17

A patio with a wooden table and chairs, a door with a number, and a mailbox.

12. Charming Accommodations in the Hamptons

Sag Harbor

￥79,192 total

includes taxes & fees

Nov 16 - Nov 17

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

Sag Harbor

maria m.

￥97,109 total

includes taxes & fees

Nov 16 - Nov 17

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

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

Clinton

Marcy C.

￥40,440 total

includes taxes & fees

Nov 19 - Nov 20

A beach with waves, a clear sky, and a sandy shore.

15. 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

￥37,514 total

includes taxes & fees

Nov 16 - Nov 17

A deck with outdoor furniture, a grill, and a potted plant.

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

Greenport

Jeannette M.

￥134,482 total

includes taxes & fees

Dec 2 - Dec 3

A serene lakeside setting with a gazebo and a bird feeder.

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

Southold

Doran R.

￥75,543 total

includes taxes & fees

Nov 23 - Nov 24

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

Westbrook Center

Mason T.

￥44,660 total

includes taxes & fees

Nov 16 - Nov 17

An outdoor seating area with wicker furniture, a fire feature, and glasses of red wine.

19. American Beech in Greenport - Deluxe King 6

Greenport

Jeffrey

￥54,377 total

includes taxes & fees

Nov 16 - Nov 17

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

East Lyme

Agatha C.

￥29,833 total

includes taxes & fees

Nov 16 - Nov 17

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Find vacation rentals that suit your style

Top Dering Harbor Hotel Reviews

A beach with sun loungers and umbrellas, a sandy path, and a view of the water.

Silver Sands Motel & Beach Bungalows

Greenport

10/10 Excellent

Nicole

The Harbor Front Inn

Greenport

10/10 Excellent

Maureen

A two-story house with a covered patio, outdoor seating, and a well-maintained lawn.

Zey Hotel

Greenport

10/10 Excellent

Jennifer

A modern outdoor seating area with two wicker chairs and a small table, overlooking a body of water and a wooden deck.

The Shoals Suites and Slips

Southold

10/10 Excellent

William

A spacious room with wicker furniture, large windows, and a view of the sea.

Sound View Greenport

Greenport

10/10 Excellent

Marilyn

A serene lakeside view with two Adirondack chairs facing the water, surrounded by autumn foliage.

House on Chase Creek

The Heights

10/10 Excellent

Damon

An outdoor patio area with string lights, tables, chairs, and a fire pit.

The Chequit

The Heights

10/10 Excellent

Joseph

A modern bathroom with a large mirror, wooden vanity, and a sink. There is a chair and a small table in the adjacent living area, with a sofa and a view of the outdoors.

The Bentley Hotel Southampton

Southampton

10/10 Excellent

Jennifer

The Menhaden

Greenport

10/10 Excellent

Anonymous traveler

A spacious hallway with a fireplace, a large window, and a built-in shelving unit.

Sag Harbor Inn

Sag Harbor

10/10 Excellent

Anonymous traveler

Cliffside Resort Condominiums

Greenport

10/10 Excellent

Jeannine

A living room with a stone fireplace, grey sofas, and a coffee table.

The Captain Stannard

Westbrook Center

10/10 Excellent

Julie

A two-story house with a porch, multiple windows, and a well-maintained lawn.

Inn at Harbor Hill Marina

Niantic

10/10 Excellent

NianticQuaint

A marina with boats docked, a fire pit table, and outdoor seating.

Saybrook Point Resort & Marina

Old Saybrook Center

10/10 Excellent

Robin

A large, two-story house with a well-maintained garden and a pathway leading to the entrance.

The 1770 House Restaurant & Inn

East Hampton

10/10 Excellent

Anonymous traveler

A modern building with a wooden exterior, a balcony, and a pathway lined with potted plants and stepping stones.

Journey East Hampton

East Hampton North

10/10 Excellent

Brittany

Find out more about Dering Harbor

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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.

Dering Harbor Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Dering Harbor vacation rentals

1. Cliffside Resort Condominiums

2. North Fork Resort

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. Windward Shores Ocean Resort

10. Northfork Townhouse walk to all

11. Renovated Townhouse walk to all

12. Charming Accommodations in the Hamptons

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

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

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

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

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

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

19. American Beech in Greenport - Deluxe King 6

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

Find vacation rentals that suit your style

Top Dering Harbor Hotel Reviews

Silver Sands Motel & Beach Bungalows

10/10 Excellent

Find out more about Dering Harbor

Frequently Asked Questions

Can I find vacation rentals in Dering Harbor?

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

What can I see and do in Dering Harbor?

What are vacation rentals like in Dering Harbor?