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Search results; Over 1,000 homes in Southold

Top guest favourite
Room in Greenport
Cozy village home
1 double bed, 1 bathroom
9–14 Aug
4.95 out of 5 average rating, 210 reviews
Top guest favourite
Flat in Sag Harbor
Artists pet friendly apartment and cabin, sauna.
1 bedroom, 1 bed, 1 bathroom
1–6 Aug
5.0 out of 5 average rating, 13 reviews
Home in East Hampton
NEW - East Hampton w/ Pool - Close to town & beach
5 bedrooms, 7 beds, 4 bathrooms
8–13 Sept
New place to stay
Top guest favourite
Room in Sag Harbor
Sag Harbor Home, Perfect for the Solo Traveler
2 beds, 1 bathroom
8–13 Aug
4.96 out of 5 average rating, 256 reviews
Top guest favourite
Room in Westbrook
The Captain James Suite
1 king bed, 1 bathroom
3–8 Aug
4.92 out of 5 average rating, 102 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
Guest favourite
Home in East Hampton
Chic house NW Woods. Massive 50 ft heated pool.
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Rooms in Greenport
Chestnut View Room own private bathroom
2 bedrooms, 3 queen beds, No bathroom
23–28 Aug
5.0 out of 5 average rating, 93 reviews
Top guest favourite
Guest house in Shelter Island
Bayfront 1BR/2BR detached guesthouse with pool
1 bedroom, 2 beds, 1 bathroom
1–6 Aug
4.99 out of 5 average rating, 74 reviews
Flat in Montauk
Exclusive Sunset Views in the Heart of Montauk
1 bedroom, 1 bed, 1 bathroom
7–12 Sept
New place to stay
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
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, 17 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
Home in Old Lyme
Traditional Family Beach House
6 bedrooms, 10 beds, 2.5 bathrooms
27 Sept – 4 Oct
Top guest favourite
Home in Sag Harbor
The Cooper-Burke House
1 bedroom, 1 queen bed, 1 bathroom
4–9 Oct
4.89 out of 5 average rating, 113 reviews
Home in East Hampton
Fabulous sunsets
4 bedrooms, 6 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 45 reviews
Top guest favourite
Cottage in Greenport
Greenport Beachfront Cottage
1 bedroom, 2 beds, 1 bathroom
14–19 Sept
4.95 out of 5 average rating, 20 reviews
Top guest favourite
Home in Old Saybrook
Waterfront Oasis 4Bdr/2b
4 bedrooms, 4 beds, 2 bathrooms
11–16 Oct
5.0 out of 5 average rating, 16 reviews