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Search results; Over 1,000 homes in Southold

Guest favourite
Flat in Southold
Bright, Southold Studio Apt near beach & town
Studio, 2 beds, 1 private bathroom
2–7 Aug
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4.95 out of 5 average rating, 149 reviews
Apartment in Greenport
Water front, sunsets, sail boats, 30 day minimum
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 2 beds, 2 bathrooms
1–6 Aug
Top guest favourite
Room in Greenport
Cozy village home
4.95 out of 5 average rating, 210 reviews, 1 double bed, 1 bathroom
9–14 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
Room in Westbrook
The Captain James Suite
4.92 out of 5 average rating, 102 reviews, 1 king bed, 1 bathroom
3–8 Aug
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
Room in Greenport
Greenport Village Private Room w/separate entrance
4.97 out of 5 average rating, 152 reviews, 1 queen bed, 1 bathroom
16–21 Aug
Top guest favourite
Rooms in Greenport
Chestnut View Room own private bathroom
5.0 out of 5 average rating, 93 reviews, 2 bedrooms, 3 queen beds, No bathroom
23–28 Aug
Guest favourite
Home in East Hampton
Chic house NW Woods. Massive 50 ft heated pool.
5.0 out of 5 average rating, 19 reviews, 3 bedrooms, 4 beds, 2 bathrooms
7–12 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
1–6 Aug
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
Home in Old Lyme
Traditional Family Beach House
6 bedrooms, 10 beds, 2.5 bathrooms
27 Sept – 4 Oct
Top guest favourite
Home in East Lyme
Charming Cottage in Private Oak Grove Beach
4.97 out of 5 average rating, 72 reviews, 3 bedrooms, 6 beds, 1 bathroom
8–13 Nov
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 East Hampton
Fabulous sunsets
5.0 out of 5 average rating, 45 reviews, 4 bedrooms, 6 beds, 2 bathrooms
27 Sept – 2 Oct
Home in East Hampton
Tranquil Springs Cottage
5.0 out of 5 average rating, 4 reviews, 2 bedrooms, 2 beds, 1 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
Home in Sag Harbor
The Cooper-Burke House
4.89 out of 5 average rating, 113 reviews, 1 bedroom, 1 bed, 1 bathroom
4–9 Oct
Guest favourite
Home in Orient
Newly renovated cottage steps to Jitney and shops
5.0 out of 5 average rating, 8 reviews, 2 bedrooms, 3 beds, 1 bathroom
22–27 Aug