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Search results; Over 1,000 homes in Southold

Guest favourite
Home in Southold
Luxury Southold waterfront home, heated pool & spa
4 bedrooms, 4 beds, 4 private bathrooms
29 Aug – 5 Sept
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5.0 out of 5 average rating, 12 reviews
Superhost
Flat in Cutchogue
Cozy North Fork Hideaway
1 bedroom, 1 bed, 1 bathroom
1–6 Aug
New place to stay
Top guest favourite
Room in Sag Harbor
Sag Harbor Home, Perfect for the Solo Traveler
2 beds, 1 bathroom
9–14 Aug
4.96 out of 5 average rating, 256 reviews
Top guest favourite
Room in Greenport
Greenport Village Private Room w/separate entrance
1 queen bed, 1 bathroom
23–28 Aug
4.97 out of 5 average rating, 153 reviews
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Guest house in East Hampton
Peaceful cottage
1 bedroom, 1 bed, 1.5 bathrooms
23–28 Sept
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Room in Greenport
Home on Sterling Harbor, Greenport
1 queen bed, 1 bathroom
23–28 Aug
4.96 out of 5 average rating, 223 reviews
Top guest favourite
Cottage in Water Mill
Head of Pond House - Waterfront Cottage
1 bedroom, 2 king beds, 1 bathroom
25–30 Oct
4.97 out of 5 average rating, 79 reviews
Top guest favourite
Room in East Hampton
Peaceful Suite w/Pool, Hot tub, Private Entry.
1 queen bed, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Flat in Old Saybrook
Charming Center of it All Location
2 bedrooms, 2 beds, 1 bathroom
1–6 Aug
4.99 out of 5 average rating, 68 reviews
Top guest favourite
Guest suite in East Hampton
Hamptons Dream Suite
1 bedroom, 3 beds, 1 bathroom
2–7 Aug
4.98 out of 5 average rating, 160 reviews
Guest favourite
Home in East Marion
Heavenly Craftsman Home
2 bedrooms, 4 beds, 1.5 bathrooms
1–6 Aug
4.89 out of 5 average rating, 9 reviews
Home in Greenport
NEW 3BR Coastal Getaway|Walk to Beach|1 Mi to Town
3 bedrooms, 5 beds, 1.5 bathrooms
1–6 Aug
Guest favourite
Rooms in Shelter Island
Room in Charming Coastal Cottage
2 bedrooms, 1 bed, 2 bathrooms
13–18 Sept
4.96 out of 5 average rating, 26 reviews
Top guest favourite
Guest house in Shelter Island
Bayfront 1BR/2BR detached guesthouse with pool
1 bedroom, 2 beds, 1 bathroom
7–12 Sept
4.99 out of 5 average rating, 76 reviews
Top guest favourite
Home in East Lyme
Charming Cottage in Private Oak Grove Beach
3 bedrooms, 6 beds, 1 bathroom
8–13 Nov
4.97 out of 5 average rating, 73 reviews
Top guest favourite
Cottage in Old Lyme
The Solo Shore Cottage | Walk to Beach + Sun Porch
2 bedrooms, 4 beds, 1 bathroom
18–23 Aug
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Guest suite in Shelter Island
Chic and Cozy Suite with Private Entrance
1 bedroom, 1 bed, 1 bathroom
2–7 Aug
4.98 out of 5 average rating, 53 reviews
Top guest favourite
Home in East Hampton
Hamptons Beach House
4 bedrooms, 5 beds, 3 bathrooms
22–27 Sept
5.0 out of 5 average rating, 17 reviews
Guest favourite
Home in East Marion
Charming North Fork escape by the beach
3 bedrooms, 4 beds, 2 bathrooms
8–15 Sept
5.0 out of 5 average rating, 12 reviews