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Search results; Over 1,000 homes in Southold

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
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
Flat in Sag Harbor
Artists pet friendly apartment and cabin, sauna.
1 bedroom, 1 bed, 1 bathroom
10–15 Aug
5.0 out of 5 average rating, 14 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
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
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
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
Top guest favourite
Home in Sag Harbor
Sag Harbor Summer House
3 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
5.0 out of 5 average rating, 10 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
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
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
Room in Sag Harbor
Room 1 Bed & Breakfast in the Heart of Sag Harbor
1 bed, 1 bathroom
17–22 Oct
5.0 out of 5 average rating, 14 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
Home in East Hampton
Springs Modern
3 bedrooms, 3 beds, 2.5 bathrooms
10–17 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Guest suite in East Hampton
Hamptons Dream Suite
1 bedroom, 3 beds, 1 bathroom
2–7 Aug
4.98 out of 5 average rating, 160 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, 14 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
Top guest favourite
Home in Clinton
The Connecticut Cottage | Historic Modern Charm
2 bedrooms, 2 beds, 2 bathrooms
23–28 Aug
4.95 out of 5 average rating, 20 reviews