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Search results; Over 1,000 homes in Southold

Guest favorite
This waterfront Southold house gives you a heated pool, dock, and cabana
4 bedrooms, 5 beds, 3 private baths
Aug 22 – 27
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4.9 out of 5 average rating, 84 reviews
Top guest favorite
Private room
This restored 1859 Italianate in Greenport gives you a private room and patio
5.0 out of 5 average rating, 98 reviews, 2 bedrooms, 3 queen beds, No bathroom
Sep 6 – 11
Top guest favorite
This Saybrook Point cottage gives you a sunny porch and quiet private yard
4.96 out of 5 average rating, 23 reviews, 2 bedrooms, 3 beds, 1 bath
Sep 7 – 12
This recently renovated Old Lyme house puts you steps from the beach
New place to stay, 2 bedrooms, 2 beds, 2 baths
Sep 14 – 19
Guest favorite
This newly built Shelter Island cottage puts you right on the water with dock access
5.0 out of 5 average rating, 6 reviews, 1 bedroom, 2 beds, 1 bath
Aug 24 – 29
Top guest favorite
This Laurel guesthouse gives you a fireplace, patio fire pit, and a kayak
5.0 out of 5 average rating, 35 reviews, 2 bedrooms, 2 beds, 1.5 baths
Sep 8 – 13
Guest favorite
Bay views and a heated saltwater pool greet you at this Greenport house
4.88 out of 5 average rating, 16 reviews, 3 bedrooms, 4 beds, 2 baths
Oct 4 – 9
Top guest favorite
This Niantic house puts you half a mile from a private beach community
4.99 out of 5 average rating, 114 reviews, 3 bedrooms, 6 beds, 2.5 baths
Sep 8 – 13
Superhost
Wake to the waves at this coastal-inspired Montauk house near Ditch Plains Beach
4 bedrooms, 5 beds, 2 baths
Aug 31 – Sep 6
Top guest favorite
This 1960s bungalow on Gardiner’s Bay gives you a private beach and bay views
5.0 out of 5 average rating, 24 reviews, 2 bedrooms, 7 beds, 1.5 baths
Sep 13 – 18
Guest favorite
This bright Springs house on a quiet cul-de-sac gives you a private backyard and hammock
5.0 out of 5 average rating, 5 reviews, 4 bedrooms, 5 beds, 2.5 baths
Sep 8 – 13
Superhost
This renovated Old Saybrook house puts you a 2-minute walk from the beach
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 4 beds, 2 baths
Sep 8 – 13
Top guest favorite
Water views and a fire pit greet you at this Madison beach cottage
4.9 out of 5 average rating, 58 reviews, 2 bedrooms, 3 beds, 2 baths
Aug 30 – Sep 4
Guest favorite
This newly built Long Island house gives you a private pool and alfresco dining
5.0 out of 5 average rating, 8 reviews, 3 bedrooms, 5 beds, 3 baths
Aug 30 – Sep 4
This rustic Napeague bungalow gives you private beach access and pine forest views
New place to stay, 3 bedrooms, 3 beds, 1 bath
Aug 30 – Sep 4
Guest favorite
This East Hampton home gives you a heated pool and lush half-acre grounds
5.0 out of 5 average rating, 30 reviews, 3 bedrooms, 3 beds, 2 baths
Sep 9 – 15
This sun-filled North Haven house gives you a heated pool, spa, and fire pit
5.0 out of 5 average rating, 3 reviews, 5 bedrooms, 7 beds, 3 baths
Aug 13 – 18
Top guest favorite
This renovated Sag Harbor ranch gives you a heated saltwater pool and outdoor sauna
5.0 out of 5 average rating, 13 reviews, 3 bedrooms, 4 beds, 2 baths
Sep 7 – 12
Top guest favorite
This South Cove cottage gives you a private backyard with a fire pit and outdoor TV
4.98 out of 5 average rating, 165 reviews, 2 bedrooms, 3 beds, 1 bath
Sep 28 – Oct 3