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Vacation rentals in Southold

Vacation rentals in Southold

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Southold

Guests agree: these stays are highly rated for location, cleanliness, and more.

  • Southold Cottage w/ View, Near Vineyards Greenport
    SUPERHOSTPrivate room · 2 guests · 1 bed · 1 shared bath
    Southold Cottage w/ View, Near Vineyards Greenport

    Our Southold cottage is quintessential North Fork living. Just feet to the Peconic Bay where you can kayak or just relax. 4 minutes to the "Wine Trail" and farms. Including Sparkling Point, Raphael, and Osprey Dominion. Minutes to town w/great shops and a short trip to Greenport. We're a quick Uber ride from the LIRR and have bicycles and kayaks for your use. We're nestled on a private road where you can listen to nature at sunset, see shooting stars at night, or just sit and enjoy the view.

    What guests are saying:

    “From the moment we arrived we were made welcome by Beth and Rob. Their hospitality was second to none and their local knowledge and tips proved invaluable. The room and bed are comfortable and opens out into a sun room then large deck and garden with plenty of different options for seating in sun or shade. The nearby lakeside location is lovely with a family of swans you can feed. Bathroom facilities are shared but don’t let this put you off as Beth and Rob are often out so sharing didn’t cause any issues. We loved coming back after a long day sightseeing to just relax. If you want to experience real life in Southold this is the place to be- a lovely homely atmosphere with Rob and Beth’s eclectic choice of furnishings . We loved it!”

  • Sweet Southold Charmer
    SUPERHOSTEntire cottage · 4 guests · 2 beds · 1 bath
    Sweet Southold Charmer

    Welcome to my incredibly cozy Southold cottage. Located steps to the Peconic Bay, village of Southold and a short lovely bike ride to the beach. This 2 bedroom 1 bathroom home has all you need for a memorable vacation. We provide discounts for 14 day stays. Please send inquiries for details.

    What guests are saying:

    “Amazing home. Super stylish and super comfortable, I got some of the best sleep here honestly. The home is tucked away, and surrounded by trees, though other homes are near- this cabin still felt very secluded and private. The yard is lovely, I enjoyed running around with our dog, and even exercising out here. On top of all this Erin is super friendly, gave us ample information about the house, and was available for any questions or concerns. Also the house was super clean!”

  • Cottage on the Great Pond
    SUPERHOSTEntire cottage · 4 guests · 3 beds · 1.5 baths
    Cottage on the Great Pond

    In the heart of wine country is the adorable , nautical inspired cottage surrounded by nature, on a beautiful freshwater pond, a quick walk or bike ride away from a beautiful beach on Long Island Sound. Hiking, fishing, wine tours, farmstands abound!

    What guests are saying:

    “Wonderfully cozy and the perfect “in the woods” vibe we were going for. Quite and off the beaten path, but close enough to amenities. It was so lovely to wake up in hee morning and see the lake right out the window! Everything was clean and Eileen was super quick with communication which I really appreciated!”

Vacation rentals for every style

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Popular amenities for Southold vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Southold

Sweet Southold Charmer
SUPERHOSTEntire cottage
Sweet Southold Charmer
Price:$516 CAD/night
Southold Cottage w/ View, Near Vineyards Greenport
SUPERHOSTPrivate room
Southold Cottage w/ View, Near Vineyards Greenport
Price:$227 CAD/night
Cottage on the Great Pond
SUPERHOSTEntire cottage
Cottage on the Great Pond
Price:$275 CAD/night
Secluded Home w/Pool in Heart of LI Wine Region!
Entire house
Secluded Home w/Pool in Heart of LI Wine Region!
Price:$673 CAD/night
Chic waterfront home with private dock
SUPERHOSTEntire house
Chic waterfront home with private dock
Price:$998 CAD/night
Bridgehampton Private Loft Walk to Town Monthly
Tiny house
Bridgehampton Private Loft Walk to Town Monthly
Price:$90 CAD/night
Waterfront North Fork/Southold Beach House
Entire house
Waterfront North Fork/Southold Beach House
Price:$516 CAD/night
New home across from the water!
Entire house
New home across from the water!
Price:$516 CAD/night
Walk to Vineyards, Beaches, Farms & Town
SUPERHOSTEntire guest suite
Walk to Vineyards, Beaches, Farms & Town
Price:$241 CAD/night
Walk to it all! - Eat, Drink, Beach, Shop - Apt #2
SUPERHOSTEntire house
Walk to it all! - Eat, Drink, Beach, Shop - Apt #2
Price:$207 CAD/night
Village suite w/private entry near the beach
SUPERHOSTEntire guest suite
Village suite w/private entry near the beach
Price:$241 CAD/night
Spectacular waterfront, sunset views, immaculate
Entire house
Spectacular waterfront, sunset views, immaculate
Price:$448 CAD/night
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