Dering Harbor Holiday Rentals

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Our top choices for Dering Harbor holiday rentals

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (40 reviews)
"Many local restaurants near by. Christy's for breakfast was very good. "
United States
Benjamin H.
The price is AU$254
includes taxes & fees
28 Apr - 29 Apr
1-bedroom cottage with Grove Beach 🏖️ access.

North Fork Cottages & RV Resort

North Fork Cottages & RV Resort
3.0 star property
Greenport
8.6 out of 10, Excellent, (11 reviews)
"great place to stay, clean and quiet....loved it"
United States
Darlin
The price is AU$294
includes taxes & fees
28 Apr - 29 Apr
North Fork Cottages & RV Resort

Floating Nest on Private River. Serene Views & Ultimate Relaxation

Floating Nest on Private River. Serene Views & Ultimate Relaxation
Old Lyme
The price is AU$520
includes taxes & fees
26 Apr - 27 Apr
Floating Nest on Private River. Serene Views & Ultimate Relaxation

Insta-worthy Couples Retreat: Perfect for romantic getaway!

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (54 reviews)
"Adorable cottage. Nice location. "
United States
Janet B.
The price is AU$382
includes taxes & fees
27 Apr - 28 Apr
Insta-worthy Couples Retreat: Perfect for romantic getaway!

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (311 reviews)
"Amazing stay! Place was perfect and staff was so friendly."
United States
Heather
The price is AU$275
includes taxes & fees
26 Apr - 27 Apr
Windward Shores Ocean Resort

Freeboard at Soundview · Beach+Ocean+Sunrise

Freeboard at Soundview · Beach+Ocean+Sunrise
Old Lyme
9.2 out of 10, Wonderful, (9 reviews)
"Great location and a nice room!"
United States
Angela M.
The price is AU$367
includes taxes & fees
28 Apr - 29 Apr
Freeboard at Soundview · Beach+Ocean+Sunrise

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (251 reviews)
"Convenient parking and proximity to all."
United States
Rosemaria
The price is AU$292
includes taxes & fees
29 Apr - 30 Apr
Cliffside Resort Condominiums

Beach Cottage, private beach and pass

Beach Cottage, private beach and pass
East Lyme
10.0 out of 10, Exceptional, (11 reviews)
"It was PERFECT way to spend USCGA Parent’s Weekend!!"
United States
Kerri G.
The price is AU$663
includes taxes & fees
14 May - 15 May
Beach Cottage, private beach and pass

Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
Waterford
10.0 out of 10, Exceptional, (22 reviews)
"The home was exactly as described and well appointed, yet charming and cozy. Great location near Niantic, Stonington and Mystic. Perfect for a sister’s birthday getaway. "
United States
Dianne B.
The price is AU$483
includes taxes & fees
11 May - 12 May
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

Safari Tent Glamping,S5-CedarPt, East Hampton, NY

Safari Tent Glamping,S5-CedarPt, East Hampton, NY
East Hampton
8.6 out of 10, Excellent, (4 reviews)
"We loved our tent, the view was great. The bed was super comfortable. We will definitely come back and hopefully stay longer. Also, the pizza is so good as was the watermelon Margherita."
United States
Jennifer
The price is AU$457
includes taxes & fees
22 May - 23 May
Safari Tent Glamping,S5-CedarPt, East Hampton, NY

Safari Tent Glamping,S10-CedarPt, East Hampton, NY

Safari Tent Glamping,S10-CedarPt, East Hampton, NY
East Hampton
The price is AU$450
includes taxes & fees
25 May - 26 May
Safari Tent Glamping,S10-CedarPt, East Hampton, NY

Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (236 reviews)
"Great place to stay for small family "
United States
DongHo
The price is AU$294
includes taxes & fees
17 May - 18 May
Driftwood Resort

The Bay Cottage · Rocky Neck Park, Beach & Niantic

The Bay Cottage · Rocky Neck Park, Beach & Niantic
East Lyme
9.0 out of 10, Wonderful, (4 reviews)
"This house suited our needs for a place to stay while attending a nearby family reunion. Communication and check in were great and the house is very comfortable (very nice mattresses, sheets, pillows)."
United States
Sarah G.
The price is AU$547
includes taxes & fees
28 Apr - 29 Apr
The Bay Cottage · Rocky Neck Park, Beach & Niantic

American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.2 out of 10, Wonderful, (5 reviews)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is AU$375
includes taxes & fees
27 Apr - 28 Apr
American Beech in Greenport - Petite King Room 7

Keel at Soundview · Beach+OceanView+Sunrise

Keel at Soundview · Beach+OceanView+Sunrise
Old Lyme
10.0 out of 10, Exceptional, (1 review)
"This is a must property for any vacationer traveling to Long Island. You will fall in love with quiet evenings after delightful beach walks. Don’t forget the therapeutic ocean air! Within very short walking distance, you are near The Pavilion and the famous Kokomo’s Restaurant. Kokomo’s is the best ocean restaurant in Old Lyme for a reason, with fantastic ocean views and an unmatched family dining experience. As Old Lyme begins its long-awaited restoration project, this beach apartment will...
United States
Jennivere
The price is AU$389
includes taxes & fees
28 Apr - 29 Apr
Keel at Soundview · Beach+OceanView+Sunrise

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

Safari Tent Glamping,D27-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (2 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
The price is AU$464
includes taxes & fees
21 May - 22 May
Safari Tent Glamping,D27-CedarPt, East Hampton, NY

Stylish Modern Stay Steps from the Ocean

Stylish Modern Stay Steps from the Ocean
Clinton
10.0 out of 10, Exceptional, (1 review)
"Very Clean and New. Location very convenient to Shopping , Coffee and Winery. Place very very small but Shower was huge and token gifts such as wine and toiletries a big plus . As well as guest for TV for Netflix. Added bonus outdoor space makes up for lack of living room. I would recommend this place and stay again for sure. Also, conveniently located to major highway and safe. "
United States
Kelly Z.
The price is AU$374
includes taxes & fees
26 Apr - 27 Apr
Stylish Modern Stay Steps from the Ocean

Waterfront Escape- 3BR Coastal Cottage w/ Boat Launch & Near Niantic Main Street

Waterfront Escape- 3BR Coastal Cottage w/ Boat Launch & Near Niantic Main Street
Waterford
10.0 out of 10, Exceptional, (4 reviews)
"Great location and extremely clean. I would definitely recommend and stay again. "
United States
Zach S.
The price is AU$613
includes taxes & fees
26 Apr - 27 Apr
Waterfront Escape- 3BR Coastal Cottage w/ Boat Launch & Near Niantic Main Street

Rogers Lake House (87) · CT College+Beach+USCGA

Rogers Lake House (87) · CT College+Beach+USCGA
Old Lyme
10.0 out of 10, Exceptional, (6 reviews)
"Host was very responsive. Property as described. We would stay again! "
United States
john18250
The price is AU$707
includes taxes & fees
11 May - 12 May
Rogers Lake House (87) · CT College+Beach+USCGA

Designer East Hampton Farmhouse Bike to Amagansett, Ocean Beaches, Seasonal Pool

Designer East Hampton Farmhouse Bike to Amagansett, Ocean Beaches, Seasonal Pool
East Hampton North
The price is AU$1,393
includes taxes & fees
28 Apr - 29 Apr
Designer East Hampton Farmhouse Bike to Amagansett, Ocean Beaches, Seasonal Pool
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

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$254 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?

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping: This holiday home rental outside of Dering Harbor offers an outdoor pool, a patio and a BBQ to help you feel perfectly comfortable 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. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

What can I see and do in Dering Harbor?

While exploring the area, visit family-friendly sights like Railroad Museum of Long Island, or get outside and enjoy nature at Sunset Beach. In the wider area, you’ll find Greenport Carousel and Gardiner's Bay Country Club.

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.