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Search results; Over 1,000 homes in Southold

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
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
4–9 Aug
Top guest favourite
Rooms in Greenport
Chestnut View Room own private bathroom
5.0 out of 5 average rating, 94 reviews, 2 bedrooms, 3 queen beds, No bathroom
23–28 Aug
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
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
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
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
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
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
Room in Greenport
Greenport Village Private Room w/separate entrance
4.97 out of 5 average rating, 153 reviews, 1 queen bed, 1 bathroom
16–21 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 Old Lyme
Traditional Family Beach House
6 bedrooms, 10 beds, 2.5 bathrooms
27 Sept – 4 Oct
Top guest favourite
Home in Old Saybrook
Waterfront Oasis 4Bdr/2b
5.0 out of 5 average rating, 16 reviews, 4 bedrooms, 4 beds, 2 bathrooms
11–16 Oct
Top guest favourite
Cottage in Greenport
Greenport Beachfront Cottage
4.95 out of 5 average rating, 20 reviews, 1 bedroom, 2 beds, 1 bathroom
14–19 Sept
Top guest favourite
Guest suite in Shelter Island
Chic and Cozy Suite with Private Entrance
4.98 out of 5 average rating, 52 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Aug
Top guest favourite
Flat in Greenport
Greenport Condo with Stunning Views & Beach Access
5.0 out of 5 average rating, 24 reviews, 2 bedrooms, 4 beds, 2 bathrooms
30 Aug – 4 Sept
Home in East Hampton
Springs Modern
5.0 out of 5 average rating, 3 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
10–17 Sept
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