Dering Harbor Holiday Rentals from AU$234: Search Short-Term Rentals

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Dering Harbor holiday rentals

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

1. North Fork Resort

Greenport

Altynai

includes taxes & fees

1 Nov - 2 Nov

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

2. Cliffside Resort Condominiums

Greenport

William

includes taxes & fees

12 Nov - 13 Nov

A beach with people relaxing on chairs and sunbathing.

3. Harbor Heights

Pipes Cove

Steven R.

includes taxes & fees

8 Nov - 9 Nov

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.

includes taxes & fees

17 Nov - 18 Nov

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

5. The SandPiper

Pipes Cove

Manuela C.

includes taxes & fees

10 Nov - 11 Nov

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.

includes taxes & fees

2 Nov - 3 Nov

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

7. American Beech in Greenport - Petite King Room 7

Greenport

Paul F.

includes taxes & fees

1 Nov - 2 Nov

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

8. Beach Block Hideaway

Pipes Cove

Teresa C.

includes taxes & fees

3 Nov - 4 Nov

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.

includes taxes & fees

9 Nov - 10 Nov

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

10. Beachfront Greenport Villa

Greenport

Kate R.

includes taxes & fees

11 Nov - 12 Nov

11. Driftwood Resort

Montauk

Julian

includes taxes & fees

30 Oct - 31 Oct

12. Windward Shores Ocean Resort

Napeague

Banessa

includes taxes & fees

1 Nov - 2 Nov

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.

includes taxes & fees

16 Nov - 17 Nov

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

14. Northfork Townhouse walk to all

Greenport

Beth R.

includes taxes & fees

11 Nov - 12 Nov

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.

includes taxes & fees

30 Oct - 31 Oct

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

includes taxes & fees

9 Nov - 10 Nov

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.

includes taxes & fees

1 Nov - 2 Nov

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.

includes taxes & fees

8 Nov - 9 Nov

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.

includes taxes & fees

1 Nov - 2 Nov

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

includes taxes & fees

2 Nov - 3 Nov

View all properties

Find holiday rentals that suit your style

Apartments

Aparthotels

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Dering Harbor Hotel Reviews

The Bentley Hotel Southampton

10/10 Excellent

"My wife and I came here for a quick getaway and it was amazing! Room was very spacious, clean and ha a cute nice balcony. It was during the off season so the pool was closed already, but we knew that in advance. Staff was friendly and helpful. Great place would recommend and come back again."

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 holiday rentals

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

Dering Harbor holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Dering Harbor holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Dering Harbor holiday rentals we have selected for you start as low as AU$234 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Dering Harbor rentals

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

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 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?

Bayfront 5 bedrooms family home. Panoramic sea view from all rooms: This holiday home rental outside of Dering Harbor is located by the ocean, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. You can relax into your holiday 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 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.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Dering Harbor holiday 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 holiday rentals that suit your style

Top Dering Harbor Hotel Reviews

The Bentley Hotel Southampton

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

Go further with the Expedia app