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Search results; Over 1,000 homes in Southold

Guest favourite
Cottage in Southold
Cozy Cottage on the Great Pond near beach.
2 bedrooms, 3 beds, 1.5 private bathrooms
11–16 Oct
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4.89 out of 5 average rating, 198 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
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
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
Greenport Village Private Room w/separate entrance
1 queen bed, 1 bathroom
23–28 Aug
4.97 out of 5 average rating, 153 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 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 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
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
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
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
Home in Sag Harbor
The Cooper-Burke House
1 bedroom, 1 queen bed, 1 bathroom
4–9 Oct
4.9 out of 5 average rating, 115 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, 75 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
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
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