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Search results; Over 1,000 homes in Southold

Home in Southold
The Shorecrest Beach House
4 bedrooms, 6 beds, 2 private bathrooms
19–24 Oct
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5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Southampton
Vogue Editors Home, Featured Hamptons Mag, Elle D.
4 bedrooms, 4 beds
12–17 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Southold
Steps from the water! Fall Northfork Retreat
3 bedrooms, 5 beds
13–18 Oct
5.0 out of 5 average rating, 20 reviews
Top guest favourite
Cottage in Cutchogue
Stunning waterfront modern farmhouse with dock.
4 bedrooms, 4 beds
4–9 Oct
4.98 out of 5 average rating, 63 reviews
Top guest favourite
Home in Cutchogue
Sunny Harbor Suite
1 bedroom, 1 queen bed
3–8 Nov
4.96 out of 5 average rating, 25 reviews
Top guest favourite
Home in Sag Harbor
Sag Harbor Charming Forest Home
3 bedrooms, 4 beds
21–26 Sept
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Home in Greenport
The North Star: Greenport Waterview Beach Getaway
3 bedrooms, 4 beds
26–31 Oct
4.96 out of 5 average rating, 69 reviews
Top guest favourite
Home in Southold
Waterfront, Dock, Boat Ramp, Hot Tub & Beaches
4 bedrooms, 8 beds
12–17 Sept
5.0 out of 5 average rating, 6 reviews
Home in Cutchogue
Steps to Beach, Vineyards, Farm Stands & Village
3 bedrooms, 3 beds
12–17 Sept
New place to stay
Top guest favourite
Cottage in Sag Harbor
Hamptons Waterfront Getaway – Stylish & Serene
2 bedrooms, 2 queen beds
25–30 Oct
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Home in East Marion
Bohemian Old Life Saving Station with Beach & Pool
6 bedrooms, 8 beds
27 Sept – 2 Oct
4.97 out of 5 average rating, 114 reviews
Top guest favourite
Place to stay in Cutchogue
Sunset Suite - walk to vineyards, beaches, & more
1 bedroom, 1 king bed
4–9 Oct
4.98 out of 5 average rating, 205 reviews
Top guest favourite
Home in Southold
Beautiful waterfront 3 bedroom home in Southold
3 bedrooms, 5 beds
13–18 Sept
5.0 out of 5 average rating, 32 reviews
Top guest favourite
Cottage in Shelter Island
3 Bedroom Cottage Gem
3 bedrooms, 4 beds
26 Sept – 1 Oct
4.97 out of 5 average rating, 129 reviews
Home in Greenport
Greenport Getaway
3 bedrooms, 3 beds
27 Oct – 1 Nov
Top guest favourite
Home in Southold
Luxury by the Sea!!
3 bedrooms, 4 beds
16–21 Sept
4.95 out of 5 average rating, 58 reviews
Top guest favourite
Rooms in Greenport
Chestnut View Room own private bathroom
2 bedrooms, 3 queen beds
10–15 Nov
5.0 out of 5 average rating, 102 reviews
Top guest favourite
Home in Laurel
Peaceful Guesthouse
2 bedrooms, 2 beds
22–27 Sept
5.0 out of 5 average rating, 38 reviews
Top guest favourite
Home in Greenport
The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub
3 bedrooms, 3 beds
24–29 Sept
4.97 out of 5 average rating, 60 reviews