Default HTG hotel image

Dering Harbor Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Dering Harbor vacation rentals

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.4 out of 10, Exceptional, (32 reviews)
"Great stay & great staff!"
United States
James
The price is CA $529
CA $604 total
includes taxes & fees
Jul 30 - Jul 31
North Fork Resort

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (49 reviews)
"We enjoyed our stay"
United States
JM B.
The price is CA $214
CA $383 total
includes taxes & fees
Jul 21 - Jul 22
1-bedroom cottage with Grove Beach 🏖️ access.

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

Safari Tent Glamping,S10-CedarPt, East Hampton, NY
East Hampton
The price is CA $302
CA $457 total
includes taxes & fees
Jul 30 - Jul 31
Safari Tent Glamping,S10-CedarPt, East Hampton, NY

The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise
Old Lyme
9.0 out of 10, Wonderful, (4 reviews)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
The price is CA $233
CA $431 total
includes taxes & fees
Jul 19 - Jul 20
The Stern at Soundview · Beach+Ocean+Sunrise

Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
Madison
The price is CA $221
CA $514 total
includes taxes & fees
Jul 21 - Jul 22
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (272 reviews)
"Comfortable and clean, and the beach location is amazing. The sunset was spectacular. We will definitely come back again!"
United States
Suzanne
The price is CA $575
CA $718 total
includes taxes & fees
Jul 22 - Jul 23
Cliffside Resort Condominiums

Safari Tent Glamping,S11-CedarPt, East Hampton, NY

Safari Tent Glamping,S11-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (2 reviews)
"Our tent was spacious and the bed was very comfortable with an incredible view of the harbor. Dave and Lee were very gracious and helpful. We especially enjoyed the Camp Store and the delicious omelets. Plus - how quiet and peaceful it was!"
United States
Lee
The price is CA $272
CA $416 total
includes taxes & fees
Jul 19 - Jul 20
Safari Tent Glamping,S11-CedarPt, East Hampton, NY

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 CA $310
CA $674 total
includes taxes & fees
Jul 20 - Jul 21
Adorable Cottage, 5 min walk to water & town

The Beach Nest-Lux Cottage Steps to the Beach

The Beach Nest-Lux Cottage Steps to the Beach
Clinton
9.8 out of 10, Exceptional, (6 reviews)
"This is exactly what we needed. Nice area, great place to walk, easy to relax. "
United States
Karol W.
The price is CA $347
CA $827 total
includes taxes & fees
Jul 19 - Jul 20
The Beach Nest-Lux Cottage Steps to the Beach

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
10.0 out of 10, Exceptional, (1 review)
"Able to walk to all the nearby restaurants with this location, including the beach. Very clean rooms with 2 TVs and controllable AC. Would definitely visit here again."
United States
Mason T.
The price is CA $219
CA $518 total
includes taxes & fees
Jul 28 - Jul 29
Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included

Lovely studio with AC in charming Sag Harbor

Lovely studio with AC in charming Sag Harbor
Sag Harbor
The price is CA $484
CA $953 total
includes taxes & fees
Jul 20 - Jul 21
Lovely studio with AC in charming Sag Harbor

Safari Tent Glamping,S7-CedarPt, East Hampton, NY

Safari Tent Glamping,S7-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (1 review)
"Thank you Cedar Point for the great accommodations. We were fortunate to have a Tent right on the Bay, great views and good times."
United States
Vasilios
The price is CA $272
CA $416 total
includes taxes & fees
Jul 19 - Jul 20
Safari Tent Glamping,S7-CedarPt, East Hampton, NY

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, (28 reviews)
"The stay was great and the host was more than kind and very helpful! "
United States
Jenna K.
The price is CA $437
CA $744 total
includes taxes & fees
Jul 19 - Jul 20
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

Keel at Soundview · Beach+OceanView+Sunrise

Keel at Soundview · Beach+OceanView+Sunrise
Old Lyme
10.0 out of 10, Exceptional, (2 reviews)
"Very peaceful community. Great accommodations!"
United States
Joseph O.
The price is CA $257
CA $466 total
includes taxes & fees
Jul 19 - Jul 20
Keel at Soundview · Beach+OceanView+Sunrise

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 CA $318
CA $710 total
includes taxes & fees
Jul 20 - Jul 21
The Bay Cottage · Rocky Neck Park, Beach & Niantic

Light, Airy, Wood-floors, 1 mile from Southampton Village, Pet Friendly, sleep 6

Light, Airy, Wood-floors, 1 mile from Southampton Village, Pet Friendly, sleep 6
Southampton
9.6 out of 10, Exceptional, (7 reviews)
"great experience"
United States
Jordan
The price is CA $491
CA $825 total
includes taxes & fees
Jul 20 - Jul 21
Light, Airy, Wood-floors, 1 mile from Southampton Village, Pet Friendly, sleep 6

Beach Cottage, private beach and pass

Beach Cottage, private beach and pass
East Lyme
10.0 out of 10, Exceptional, (13 reviews)
"An absolutely adorable and cozy cottage steps from a lovely beach. The location is great, beds were so comfortable and everything was clean and well designed. Would definitely stay here again"
United States
Maria M.
The price is CA $560
CA $994 total
includes taxes & fees
Aug 2 - Aug 3
Beach Cottage, private beach and pass

Insta-worthy Couples Retreat: Perfect for romantic getaway!

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (59 reviews)
"My family and I had an ideal stay at Kristine's beachside cottage. Highlights include a short walk to the beach, a well stocked kitchen, easy and efficient temperature controls and my kids especially loved the bunk beds! It was perfectly cozy and comfy for a family of four. We stayed here in April, but I can only imagine how lovely the screened in porch and back deck would feel during warmer months. 5 stars!"
United States
Leila N.
The price is CA $303
CA $572 total
includes taxes & fees
Aug 9 - Aug 10
Insta-worthy Couples Retreat: Perfect for romantic getaway!

Adorable Cottage with Cottage porch, walk to water & town

Adorable Cottage with Cottage porch, walk to water & town
Westbrook Center
8.8 out of 10, Excellent, (6 reviews)
"Great host and property"
United States
Kevin K.
The price is CA $408
CA $800 total
includes taxes & fees
Aug 1 - Aug 2
Adorable Cottage with Cottage porch, walk to water & town
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Dering Harbor Hotel Reviews

Find out more about Dering Harbor

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Dering Harbor. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

The Hampton Sack a cheerful relaxing beach cottage: This vacation home rental outside of Dering Harbor is equipped with a barbecue grill, air-conditioning, and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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 The Hamptons Beaches. In the larger area, you’ll find Greenport Carousel and Sunset Beach.

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.