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Search results; Over 1,000 homes in Southold

Guest favourite
Home in Southold
Stylish Beach Getaway: pool & walking location
3 bedrooms, 4 beds, 2 private bathrooms
13–18 Sept
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4.88 out of 5 average rating, 24 reviews
Home in Sag Harbor
Comfortable 3 bed in Sag Harbor
3 bedrooms, 3 beds, 4 bathrooms
12–17 Sept
New place to stay
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, 205 reviews
Top guest favourite
Rooms in Greenport
Chestnut View Room own private bathroom
2 bedrooms, 3 queen beds, No bathroom
10–15 Nov
5.0 out of 5 average rating, 102 reviews
Guest favourite
Home in Southampton
Vogue Editors Home, Featured Hamptons Mag, Elle D.
4 bedrooms, 4 beds, 7.5 bathrooms
12–17 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Cutchogue
Sunny Harbor Suite
1 bedroom, 1 queen bed, 1 bathroom
3–8 Nov
4.96 out of 5 average rating, 25 reviews
Top guest favourite
Home in Greenport
The North Star: Greenport Waterview Beach Getaway
3 bedrooms, 4 beds, 2 bathrooms
26–31 Oct
4.96 out of 5 average rating, 69 reviews
Top guest favourite
Home in Sag Harbor
Sag Harbor Charming Forest Home
3 bedrooms, 4 beds, 2 bathrooms
21–26 Sept
5.0 out of 5 average rating, 21 reviews
Guest favourite
Villa in Shelter Island
Superb Shelter Island 4 bed Designer with a Pool
3 bedrooms, 4 beds, 3 bathrooms
13–18 Sept
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in Greenport
Blue Bay Dream (Outdoor Jacuzzi, Cabana + Office)
2 bedrooms, 3 beds, 1 bathroom
4–9 Oct
4.92 out of 5 average rating, 514 reviews
Top guest favourite
Home in Southold
Beautiful waterfront 3 bedroom home in Southold
3 bedrooms, 5 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 32 reviews
Home in Cutchogue
Steps to Beach, Vineyards, Farm Stands & Village
3 bedrooms, 3 beds, 2 bathrooms
12–17 Sept
New place to stay
Top guest favourite
Cottage in Sag Harbor
Charming Cottage in Historic Sag Harbor
1 bedroom, 1 king bed, 1 bathroom
17–22 Oct
5.0 out of 5 average rating, 78 reviews
Top guest favourite
Home in Greenport
The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub
3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.97 out of 5 average rating, 60 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, 7 reviews
Top guest favourite
Home in Southold
Waterfront, Dock, Boat Ramp, Hot Tub & Beaches
4 bedrooms, 8 beds, 3 bathrooms
13–18 Sept
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Greenport
Aqua Vista
2 bedrooms, 3 beds, 1 bathroom
12–17 Oct
4.95 out of 5 average rating, 270 reviews
Guest favourite
Home in Southold
Private Waterfront Access + Hot Tub + Scenic Yard
3 bedrooms, 5 beds, 2.5 bathrooms
12–17 Sept
5.0 out of 5 average rating, 45 reviews
Top guest favourite
Home in Southold
Luxury by the Sea!!
3 bedrooms, 4 beds, 2.5 bathrooms
16–21 Sept
4.95 out of 5 average rating, 58 reviews