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Search results; Over 1,000 homes in Southold

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Top guest favourite
Guest suite in Southold
Comfortable Suite, a walk to the beach
1 bedroom, 1 bed, 1 private bathroom
27 Sept – 2 Oct
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4.94 out of 5 average rating, 156 reviews
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Guest favourite
Home in Peconic
Provence on the North Fork
3 bedrooms, 3 beds, 3 bathrooms
1–8 Sept
4.94 out of 5 average rating, 35 reviews
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Top guest favourite
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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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, 3 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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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
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Home in Water Mill
Secluded Oasis | 3 Acres, Heated Pool & Fire Pit
3 bedrooms, 5 beds, 2 bathrooms
1–6 Sept
New place to stay
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Top guest favourite
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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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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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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Top guest favourite
Place to stay in Cutchogue
Sunset Suite - walk to vineyards, beaches, & more
1 bedroom, 1 king bed, 1 bathroom
6–11 Sept
4.98 out of 5 average rating, 201 reviews
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Superhost
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, 92 reviews
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Room in Southold
The Terry Inn Master Suite
1 bed, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 3 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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Top guest favourite
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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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, 5 reviews
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Guest favourite
Home in Southold
Peconic Pearl Cottage
4 bedrooms, 5 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 7 reviews
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Home in Shelter Island
Waterfront Retreat | Spa Pool, Sauna & Dock
3 bedrooms, 3 beds, 3.5 bathrooms
13–18 Sept
New place to stay