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Dering Harbor Holiday Rentals

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Our top choices for Dering Harbor holiday rentals

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (255 reviews)
"Beautiful property- we would definitely stay there again"
United States
Allison
The price is AU$425
includes taxes & fees
23 June - 24 June
Cliffside Resort Condominiums

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.2 out of 10, Wonderful, (22 reviews)
"Great stay & great staff!"
United States
James
The price is AU$653
includes taxes & fees
30 June - 1 July
North Fork Resort

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (315 reviews)
"Nice homey room"
United States
Andrew
The price is AU$425
includes taxes & fees
10 June - 11 June
Windward Shores Ocean Resort

Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (240 reviews)
"Very close to beach"
United States
Rabia
The price is AU$444
includes taxes & fees
11 June - 12 June
Driftwood Resort

The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise
Old Lyme
10.0 out of 10, Exceptional, (3 reviews)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
The price is AU$368
includes taxes & fees
10 June - 11 June
The Stern at Soundview · Beach+Ocean+Sunrise

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (44 reviews)
"The place was super cozy and the host was wonderful! "
United States
Philip L.
The price is AU$258
includes taxes & fees
11 June - 12 June
1-bedroom cottage with Grove Beach 🏖️ access.

NEW Coastal Cottage 2 Miles to Beach + Lake Access

NEW Coastal Cottage 2 Miles to Beach + Lake Access
Clinton
10.0 out of 10, Exceptional, (4 reviews)
"We had a wonderful stay at this cottage. It was comfortable, beautifully decorated, and exceptionally clean. Even though the weather during our trip was terrible, we still thoroughly enjoyed our time there.The hosts were very helpful and provided all the information we needed about the cottage as well as local attractions and activities. Overall, it was an excellent experience, and I would absolutely give it 5 stars."
United States
Erin M.
The price is AU$445
includes taxes & fees
10 June - 11 June
NEW Coastal Cottage 2 Miles to Beach + Lake Access

Beach Cottage, private beach and pass

Beach Cottage, private beach and pass
East Lyme
10.0 out of 10, Exceptional, (12 reviews)
"It was PERFECT way to spend USCGA Parent’s Weekend!!"
United States
Kerri G.
The price is AU$986
includes taxes & fees
24 June - 25 June
Beach Cottage, private beach and pass

Adorable Cottage, 5 min walk to water & town

Adorable Cottage, 5 min walk to water & town
Westbrook Center
9.4 out of 10, Exceptional, (15 reviews)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
The price is AU$573
includes taxes & fees
10 June - 11 June
Adorable Cottage, 5 min walk to water & town

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

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Old Saybrook
9.8 out of 10, Exceptional, (10 reviews)
"Very clean & comfortable home, great host & location! "
United States
Becky W.
The price is AU$635
includes taxes & fees
10 June - 11 June
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

The Bay Cottage · Rocky Neck Park, Beach & Niantic

The Bay Cottage · Rocky Neck Park, Beach & Niantic
East Lyme
8.8 out of 10, Excellent, (6 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$603
includes taxes & fees
11 June - 12 June
The Bay Cottage · Rocky Neck Park, Beach & Niantic

PRIVATE BEACH: BEACHFRONTS & BALCONIES @ NIANTIC W/ 6 QUEENS

PRIVATE BEACH: BEACHFRONTS & BALCONIES @ NIANTIC W/ 6 QUEENS
East Lyme
9.8 out of 10, Exceptional, (23 reviews)
"I’ve stayed at this property for 3 summers in a row and every time it has been perfect. Lots of room, very clean and a perfect view!"
United States
Elisa N.
The price is AU$3,467
includes taxes & fees
12 June - 13 June
PRIVATE BEACH: BEACHFRONTS & BALCONIES @ NIANTIC W/ 6 QUEENS

Charming Accommodations in the Hamptons

Charming Accommodations in the Hamptons
Sag Harbor
The price is AU$800
includes taxes & fees
10 June - 11 June
Charming Accommodations in the Hamptons

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

Rogers Lake House (87) · CT College+Beach+USCGA
Old Lyme
10.0 out of 10, Exceptional, (7 reviews)
"Host was very responsive. Property as described. We would stay again! "
United States
john18250
The price is AU$681
includes taxes & fees
14 June - 15 June
Rogers Lake House (87) · CT College+Beach+USCGA

Beachside Bliss w/ Game Room, Gym & Golf Green

Beachside Bliss w/ Game Room, Gym & Golf Green
Westbrook
10.0 out of 10, Exceptional, (1 review)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is AU$896
includes taxes & fees
15 June - 16 June
Beachside Bliss w/ Game Room, Gym & Golf Green

Seabreeze 4 Charming Cottage walk to US Open

Seabreeze 4 Charming Cottage walk to US Open
Hampton Bays
8.8 out of 10, Excellent, (3 reviews)
"Great stay. Would stay again. "
United States
Weston B.
The price is AU$706
includes taxes & fees
10 June - 11 June
Seabreeze 4 Charming Cottage walk to US Open

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, (24 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$504
includes taxes & fees
11 June - 12 June
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

Hamptons Vacation Rental w/ Seasonal Pool!

Hamptons Vacation Rental w/ Seasonal Pool!
3.0 star property
Hampton Bays
The price is AU$1,977
includes taxes & fees
5 July - 6 July
Hamptons Vacation Rental w/ Seasonal Pool!

Town walking distance-Bridgehampton Cottage

Town walking distance-Bridgehampton Cottage
Bridgehampton
9.4 out of 10, Exceptional, (10 reviews)
"Walking distance to Bridgehampton and a short drive to sag harbor. Great for 2 couples."
United States
Jim M.
Town walking distance-Bridgehampton Cottage

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$424
includes taxes & fees
10 June - 11 June
Safari Tent Glamping,S5-CedarPt, East Hampton, NY
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$258 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?

Waterfront Escape- 3BR Coastal Cottage w/ Boat Launch & Near Niantic Main Street: This holiday home rental outside Dering Harbor is located on the waterfront, and has a patio, a BBQ and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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 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.