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Dering Harbor Vacation Rentals

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    Check prices for these dates, December 15 – 16, 2026

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    Our top choices for Dering Harbor vacation rentals

    1. Cliffside Resort Condominiums

    Terrace/patio

    2. North Fork Resort

    A rustic cabin with a wooden exterior, a front porch, and a staircase leading to the entrance.

    3. Harbor Heights

    A beach with people relaxing on chairs and sunbathing.

    4. Aqua Vista

    A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

    5. The SandPiper

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

    6. Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

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

    7. American Beech in Greenport - Petite King Room 7

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

    8. Beach Block Hideaway

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

    9. Windward Shores Ocean Resort

    Terrace/patio

    10. Northfork Townhouse walk to all

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

    11. Renovated Townhouse walk to all

    A modern kitchen with a marble island, pendant lights, and a patterned backsplash.

    12. Charming Accommodations in the Hamptons

    A patio with a wooden table and chairs, a door with a number, and a mailbox.

    13. Designer Sag Harbor Home w/ Pool + Fire Pit + Yard

    A house with a sliding glass door, a white door, and a small porch with potted plants.

    14. 1-bedroom cottage with Grove Beach 🏖️ access.

    A bedroom with a wooden bed, bedside lamps, a sofa, and a TV stand.

    15. The Stern at Soundview · Beach+Ocean+Sunrise

    A beach with waves, a clear sky, and a sandy shore.

    16. The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

    A deck with outdoor furniture, a grill, and a potted plant.

    17. North Fork Grinch Getaway & Hot Chocolate Bar. Two Bedroom Sleeps 4.

    A serene lakeside setting with a gazebo and a bird feeder.

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

    A beach with waves, a clear sky, and a sandy shore.

    19. American Beech in Greenport - Deluxe King 6

    An outdoor seating area with wicker furniture, a fire feature, and glasses of red wine.

    20. NEW private studio 1.1 miles to beach in East Lyme

    A cozy living room with a sofa, a coffee table, and a dining area with chairs.

    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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    Find vacation rentals that suit your style

    Apartments

    Aparthotels

    Condos

    Cottages

    Villas

    Top Dering Harbor Hotel Reviews

    Silver Sands Motel & Beach Bungalows

    A beach with sun loungers and umbrellas, a sandy path, and a view of the water.

    The Harbor Front Inn

    Room

    Zey Hotel

    A two-story house with a covered patio, outdoor seating, and a well-maintained lawn.

    The Shoals Suites and Slips

    A modern outdoor seating area with two wicker chairs and a small table, overlooking a body of water and a wooden deck.

    The Chequit

    An outdoor patio area with string lights, tables, chairs, and a fire pit.

    House on Chase Creek

    A serene lakeside view with two Adirondack chairs facing the water, surrounded by autumn foliage.

    Sound View Greenport

    A spacious room with wicker furniture, large windows, and a view of the sea.

    The Menhaden

    A two-story building with large windows, a sign reading "The Menhaden," and bicycles parked outside.

    The Bentley Hotel Southampton

    A modern bathroom with a large mirror, wooden vanity, and a sink. There is a chair and a small table in the adjacent living area, with a sofa and a view of the outdoors.

    Sag Harbor Inn

    A spacious hallway with a fireplace, a large window, and a built-in shelving unit.

    Cliffside Resort Condominiums

    Terrace/patio

    American Beech Hotel

    A pathway flanked by lush greenery and bamboo, leading to a building with a wooden exterior.

    Inn at Harbor Hill Marina

    A two-story house with a porch, multiple windows, and a well-maintained lawn.

    The Captain Stannard

    A living room with a stone fireplace, grey sofas, and a coffee table.

    Saybrook Point Resort & Marina

    A marina with boats docked, a fire pit table, and outdoor seating.

    Faraway Sag Harbor

    A pool area with umbrellas, potted plants, and a pathway leading to a building.

    The 1770 House Restaurant & Inn

    A large, two-story house with a well-maintained garden and a pathway leading to the entrance.

    Clinton Motel

    A hotel room with two beds, a desk, a chair, a window with curtains, and two wall-mounted lamps.

    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 $186 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 Kontokosta Winery.

    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.