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Search results; Over 1,000 homes in Southold

Guest favourite
Home in Southold
Shelter Bay Cove Waterfront Escape
3 bedrooms, 3 beds, 2 private bathrooms
8–13 Sept
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4.97 out of 5 average rating, 31 reviews
Top guest favourite
Room in Greenport
Cozy village home
1 double bed, 1 bathroom
30 Aug – 4 Sept
4.95 out of 5 average rating, 211 reviews
Top guest favourite
Rooms in Greenport
Chestnut View Room own private bathroom
2 bedrooms, 3 queen beds, No bathroom
6–11 Sept
5.0 out of 5 average rating, 95 reviews
Top guest favourite
Flat in Sag Harbor
Artists pet friendly apartment and cabin, sauna.
1 bedroom, 1 bed, 1 bathroom
10–15 Aug
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Room in Westbrook
The Captain James Suite
1 king bed, 1 bathroom
17–22 Aug
4.92 out of 5 average rating, 102 reviews
Guest favourite
Home in Sag Harbor
5 bedroom luxe home in Sag Harbor w/ heated pool
5 bedrooms, 6 beds, 5.5 bathrooms
31 Oct – 5 Nov
5.0 out of 5 average rating, 13 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
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
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
Guest favourite
Rooms in East Hampton
Treetops Room at Ober Oaks in The Hamptons
2 bedrooms, 1 king bed, 1 bathroom
2–7 Aug
4.95 out of 5 average rating, 56 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
Guest house in Shelter Island
Bayfront 1BR/2BR detached guesthouse with pool
1 bedroom, 2 beds, 1 bathroom
4–9 Aug
4.99 out of 5 average rating, 76 reviews
Home in Orient
Orient cottage in the Village
3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Cottage in Sag Harbor
Hamptons Waterfront Getaway – Stylish & Serene
2 bedrooms, 2 queen beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 18 reviews
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
Home in Greenport
NEW 3BR Coastal Getaway|Walk to Beach|1 Mi to Town
3 bedrooms, 5 beds, 1.5 bathrooms
1–6 Aug
Top guest favourite
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
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
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