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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
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
Home in Sag Harbor
Comfortable 3 bed in Sag Harbor
3 bedrooms, 3 beds, 4 bathrooms
11–16 Sept
New place to stay
Guest favourite
Home in Peconic
Provence on the North Fork
3 bedrooms, 3 beds, 3 bathrooms
2–9 Sept
4.95 out of 5 average rating, 37 reviews
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, 56 reviews
Home in Sag Harbor
Striking Waterfront 3 Bedroom on Sag Harbor Cove
3 bedrooms, 4 beds, 3 bathrooms
20–25 Sept
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
Guest favourite
Home in Shelter Island
New vacation house on the island with the pool
3 bedrooms, 5 beds, 3 bathrooms
2–7 Sept
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Rooms in Greenport
Chestnut View Room own private bathroom
2 bedrooms, 3 queen beds, No bathroom
4–9 Oct
5.0 out of 5 average rating, 100 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 Cutchogue
Sunny Harbor Suite
1 bedroom, 1 queen bed, 1 bathroom
26–31 Oct
4.96 out of 5 average rating, 25 reviews
Guest favourite
Holiday home in Orient
Private Vineyard w/Pool, Walk to Beach & Village
3 bedrooms, 4 beds, 3 bathrooms
2–7 Sept
5.0 out of 5 average rating, 23 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
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 Southold
Waterfront, Dock, Boat Ramp, Hot Tub & Beaches
4 bedrooms, 8 beds, 3 bathrooms
7–12 Sept
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Southold
Southold Escape With Large Pool on Wine Trail
3 bedrooms, 3 double beds, 2.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 20 reviews
Top guest favourite
Home in East Hampton
East Hampton Rental w/ Pool, Moments to Amenities
4 bedrooms, 5 beds, 3 bathrooms
11–16 Oct
5.0 out of 5 average rating, 93 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