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Search results; Over 1,000 homes in Southold

Guest favourite
Cottage in Southold
Cozy Cottage on the Great Pond near beach.
2 bedrooms, 3 beds, 1.5 private bathrooms
11–16 Oct
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4.89 out of 5 average rating, 202 reviews
Top guest favourite
Home in Cutchogue
Sunny Harbor Suite
1 bedroom, 1 queen bed, 1 bathroom
26–31 Oct
4.96 out of 5 average rating, 25 reviews
Top guest favourite
Cottage in Cutchogue
Stunning waterfront modern farmhouse with dock.
4 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
4.98 out of 5 average rating, 62 reviews
Guest favourite
Home in Southampton
Vogue Editors Home, Featured Hamptons Mag, Elle D.
4 bedrooms, 4 beds, 7.5 bathrooms
11–16 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Cottage in Shelter Island
3 Bedroom Cottage Gem
3 bedrooms, 4 beds, 2.5 bathrooms
6–11 Sept
4.97 out of 5 average rating, 129 reviews
Top guest favourite
Home in Greenport
The North Star: Greenport Waterview Beach Getaway
3 bedrooms, 4 beds, 2 bathrooms
19–24 Oct
4.96 out of 5 average rating, 69 reviews
Top guest favourite
Home in Southold
Steps from the water! Fall Northfork Retreat
3 bedrooms, 5 beds, 1.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 20 reviews
Home in Cutchogue
Steps to Beach, Vineyards, Farm Stands & Village
3 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
New place to stay
Top guest favourite
Home in Southold
Luxury by the Sea!!
3 bedrooms, 4 beds, 2.5 bathrooms
7–12 Sept
4.95 out of 5 average rating, 57 reviews
Top guest favourite
Home in Cutchogue
Private Oasis W/Stunning Vinyard and Pool Views
4 bedrooms, 4 beds, 3 bathrooms
6–11 Sept
4.97 out of 5 average rating, 218 reviews
Home in Sag Harbor
Striking Waterfront 3 Bedroom on Sag Harbor Cove
3 bedrooms, 4 beds, 3 bathrooms
20–25 Sept
Top guest favourite
Place to stay in Cutchogue
Sunset Suite - walk to vineyards, beaches, & more
1 bedroom, 1 king bed, 1 bathroom
4–9 Oct
4.98 out of 5 average rating, 203 reviews
Top guest favourite
Home in East Marion
Bohemian Old Life Saving Station with Beach & Pool
6 bedrooms, 8 beds, 4 bathrooms
8–15 Sept
4.97 out of 5 average rating, 114 reviews
Home in Shelter Island Heights
Creekside House Shelter Island
4 bedrooms, 5 beds, 3.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 3 reviews
Home in Sag Harbor
Comfortable 3 bed in Sag Harbor
3 bedrooms, 3 beds, 4 bathrooms
11–16 Sept
New place to stay
Top guest favourite
Rooms in Greenport
Chestnut View Room own private bathroom
2 bedrooms, 3 queen beds, No bathroom
11–16 Oct
5.0 out of 5 average rating, 101 reviews
Top guest favourite
Cottage in Sag Harbor
Hamptons Waterfront Getaway – Stylish & Serene
2 bedrooms, 2 queen beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 18 reviews
Guest favourite
Home in Greenport
Greenport Beachfront Home | Private Beach & Sunset
4 bedrooms, 7 beds, 2 bathrooms
17–22 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Sag Harbor
Sag Harbor Charming Forest Home
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 21 reviews