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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
11–16 Sept
New place to stay
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
Top guest favourite
Home in Greenport
The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub
3 bedrooms, 3 beds, 2 bathrooms
8–13 Sept
4.97 out of 5 average rating, 59 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
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
Home in Sag Harbor
Striking Waterfront 3 Bedroom on Sag Harbor Cove
3 bedrooms, 4 beds, 3 bathrooms
20–25 Sept
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
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, 100 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
Top guest favourite
Home in Shelter Island
Shelter island retreat
2 bedrooms, 2 king beds, 1 bathroom
7–12 Sept
4.97 out of 5 average rating, 172 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
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 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
Top guest favourite
Home in Southold
NoFo Family Beach House — Walk To Private Beach
4 bedrooms, 4 beds, 2 bathrooms
7–14 Sept
5.0 out of 5 average rating, 33 reviews
Top guest favourite
Home in Southold
Beautiful waterfront 3 bedroom home in Southold
3 bedrooms, 5 beds, 2 bathrooms
4–9 Sept
5.0 out of 5 average rating, 32 reviews
Top guest favourite
Room in Greenport
Cozy village home
1 double bed, 1 bathroom
13–18 Sept
4.95 out of 5 average rating, 215 reviews
Top guest favourite
Flat in Sag Harbor
Updated apartment in historic village home
1 bedroom, 2 beds, 1 bathroom
12–17 Oct
4.98 out of 5 average rating, 241 reviews
Top guest favourite
Cottage in Cutchogue
Renovated 2-Bedroom Cottage on the North Fork
2 bedrooms, 2 queen beds, 1 bathroom
12–17 Sept
5.0 out of 5 average rating, 56 reviews