Dering Harbor Vacation Rentals

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Our top choices for Dering Harbor vacation rentals

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.2 out of 10, Wonderful, (19 reviews)
"Great stay & great staff!"
United States
James
$273 nightly
The price is $312
Jun 1 - Jun 2
Total with taxes and fees
North Fork Resort

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (43 reviews)
"The host was very accommodating and very responsive. The cottage was very clean and tidy. "
United States
Rob C.
$159 nightly
The price is $180
Jun 1 - Jun 2
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (253 reviews)
"Beautiful property- we would definitely stay there again"
United States
Allison
$262 nightly
The price is $299
Jun 21 - Jun 22
Total with taxes and fees
Cliffside Resort Condominiums

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

Safari Tent Glamping,S10-CedarPt, East Hampton, NY
East Hampton
$260 nightly
The price is $298
Jun 1 - Jun 2
Total with taxes and fees
Safari Tent Glamping,S10-CedarPt, East Hampton, NY

Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (240 reviews)
"Very close to beach"
United States
Rabia
$218 nightly
The price is $249
Jun 2 - Jun 3
Total with taxes and fees
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
$220 nightly
The price is $249
Jun 1 - Jun 2
Total with taxes and fees
The Stern at Soundview · Beach+Ocean+Sunrise

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (313 reviews)
"We always stay at the Windward Shores when we go to Montauk. It is a beautiful, clean and comfortable place, and the price is great!"
United States
Joseph
$252 nightly
The price is $288
Jun 1 - Jun 2
Total with taxes and fees
Windward Shores Ocean Resort

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
$392 nightly
The price is $443
Jun 2 - Jun 3
Total with taxes and fees
Rogers Lake House (87) · CT College+Beach+USCGA

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.
$357 nightly
The price is $404
Jun 1 - Jun 2
Total with taxes and fees
Adorable Cottage, 5 min walk to water & town

Safari Tent Glamping,S4-CedarPt, East Hampton, NY

Safari Tent Glamping,S4-CedarPt, East Hampton, NY
East Hampton
$260 nightly
The price is $298
Jun 1 - Jun 2
Total with taxes and fees
Safari Tent Glamping,S4-CedarPt, East Hampton, NY

The Bay Cottage · Rocky Neck Park, Beach & Niantic

The Bay Cottage · Rocky Neck Park, Beach & Niantic
East Lyme
9.2 out of 10, Wonderful, (5 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.
$347 nightly
The price is $392
Jun 1 - Jun 2
Total with taxes and fees
The Bay Cottage · Rocky Neck Park, Beach & Niantic

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
$232 nightly
The price is $263
Jun 1 - Jun 2
Total with taxes and fees
Keel at Soundview · Beach+OceanView+Sunrise

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, (23 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.
$373 nightly
The price is $422
Jun 8 - Jun 9
Total with taxes and fees
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

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

Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
Westbrook Center
$239 nightly
The price is $271
Jun 1 - Jun 2
Total with taxes and fees
Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included

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.
$611 nightly
The price is $692
Jun 3 - Jun 4
Total with taxes and fees
Beach Cottage, private beach and pass

Charming 1-bedroom apartment with AC in Sag Harbor

Charming 1-bedroom apartment with AC in Sag Harbor
Sag Harbor
$493 nightly
The price is $563
Jun 8 - Jun 9
Total with taxes and fees
Charming 1-bedroom apartment with AC in Sag Harbor

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.
$488 nightly
The price is $523
Jun 3 - Jun 4
Total with taxes and fees
Seabreeze 4 Charming Cottage walk to US Open

Insta-worthy Couples Retreat: Perfect for romantic getaway!

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (58 reviews)
"Adorable cottage. Nice location. "
United States
Janet B.
$319 nightly
The price is $361
Jun 15 - Jun 16
Total with taxes and fees
Insta-worthy Couples Retreat: Perfect for romantic getaway!

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
$271 nightly
The price is $310
Jun 1 - Jun 2
Total with taxes and fees
Safari Tent Glamping,D27-CedarPt, East Hampton, NY

Lake House - A

Lake House - A
East Lyme
$489 nightly
The price is $553
Jun 1 - Jun 2
Total with taxes and fees
Lake House - A
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 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 $180 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 Gardiner's Bay Country Club.

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.