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Search results; Over 1,000 homes in Southold

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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
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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
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Home in Sag Harbor
Striking Waterfront 3 Bedroom on Sag Harbor Cove
3 bedrooms, 4 beds, 3 bathrooms
20–25 Sept
New place to stay
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Home in Cutchogue
Steps to Beach, Vineyards, Farm Stands & Village
3 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
New place to stay
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Home in Greenport
Greenport Beachfront Home | Private Beach & Sunset
4 bedrooms, 7 beds, 2 bathrooms
6–11 Sept
5.0 out of 5 average rating, 4 reviews
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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, 68 reviews
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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
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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
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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
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Rooms in Greenport
Chestnut View Room own private bathroom
2 bedrooms, 3 queen beds, No bathroom
20–25 Sept
5.0 out of 5 average rating, 99 reviews
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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
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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, 19 reviews
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Home in Greenport
Greenport Getaway
3 bedrooms, 3 beds, 2 bathrooms
2–7 Oct
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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
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Home in Shelter Island Heights
Creekside House Shelter Island
4 bedrooms, 5 beds, 3.5 bathrooms
7–14 Sept
5.0 out of 5 average rating, 3 reviews
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Home in Southold
Country Beach Home!
4 bedrooms, 8 beds, 2.5 bathrooms
20–25 Sept
4.95 out of 5 average rating, 22 reviews
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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
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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
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Top guest favourite
Cottage in New Suffolk
New Suffolk Beach Cottage 1 | North Fork
2 bedrooms, 3 beds, 1 bathroom
11–16 Sept
4.98 out of 5 average rating, 57 reviews