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Search results; Over 1,000 homes in Southold

Top guest favourite
Home in Southold
Luxury by the Sea!!
3 bedrooms, 4 beds, 2.5 private bathrooms
30 Aug – 4 Sept
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4.94 out of 5 average rating, 54 reviews
Top guest favourite
Room in Westbrook
The Captain James Suite
4.92 out of 5 average rating, 102 reviews, 1 king bed, 1 bathroom
3–8 Aug
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Rooms in Greenport
Chestnut View Room own private bathroom
5.0 out of 5 average rating, 95 reviews, 2 bedrooms, 3 queen beds, No bathroom
23–28 Aug
Top guest favourite
Flat in Old Saybrook
Charming Center of it All Location
4.99 out of 5 average rating, 68 reviews, 2 bedrooms, 2 beds, 1 bathroom
1–6 Aug
Top guest favourite
Cottage in Water Mill
Head of Pond House - Waterfront Cottage
4.97 out of 5 average rating, 79 reviews, 1 bedroom, 2 beds, 1 bathroom
25–30 Oct
Top guest favourite
Home in Clinton
The Connecticut Cottage | Historic Modern Charm
4.95 out of 5 average rating, 20 reviews, 2 bedrooms, 2 beds, 2 bathrooms
9–14 Aug
Guest favourite
Rooms in Shelter Island
Room in Charming Coastal Cottage
4.96 out of 5 average rating, 26 reviews, 2 bedrooms, 1 bed, 2 bathrooms
13–18 Sept
Top guest favourite
Home in East Lyme
Charming Cottage in Private Oak Grove Beach
4.97 out of 5 average rating, 73 reviews, 3 bedrooms, 6 beds, 1 bathroom
8–13 Nov
Top guest favourite
Room in Greenport
Greenport Village Private Room w/separate entrance
4.97 out of 5 average rating, 153 reviews, 1 queen bed, 1 bathroom
23–28 Aug
Top guest favourite
Room in Sag Harbor
Sag Harbor Home, Perfect for the Solo Traveler
4.96 out of 5 average rating, 256 reviews, 2 beds, 1 bathroom
8–13 Aug
Guest favourite
Home in East Marion
Charming North Fork escape by the beach
5.0 out of 5 average rating, 12 reviews, 3 bedrooms, 4 beds, 2 bathrooms
8–15 Sept
Top guest favourite
Cottage in Sag Harbor
Hamptons Waterfront Getaway – Stylish & Serene
5.0 out of 5 average rating, 17 reviews, 2 bedrooms, 2 beds, 2 bathrooms
8–13 Sept
Top guest favourite
Guest house in Shelter Island
Bayfront 1BR/2BR detached guesthouse with pool
4.99 out of 5 average rating, 74 reviews, 1 bedroom, 2 beds, 1 bathroom
9–14 Aug
Top guest favourite
Home in Sag Harbor
The Cooper-Burke House
4.89 out of 5 average rating, 114 reviews, 1 bedroom, 1 bed, 1 bathroom
4–9 Oct
Home in Orient
Orient cottage in the Village
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Oct
Home in East Hampton
NEW - East Hampton w/ Pool - Close to town & beach
New place to stay, 5 bedrooms, 7 beds, 4 bathrooms
8–13 Sept
Top guest favourite
Flat in Greenport
Greenport Condo with Stunning Views & Beach Access
4.96 out of 5 average rating, 26 reviews, 2 bedrooms, 4 beds, 2 bathrooms
30 Aug – 4 Sept
Top guest favourite
Home in East Hampton
Hamptons Beach House
5.0 out of 5 average rating, 17 reviews, 4 bedrooms, 5 beds, 3 bathrooms
22–27 Sept
Top guest favourite
Guest suite in Shelter Island
Chic and Cozy Suite with Private Entrance
4.98 out of 5 average rating, 53 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Aug