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Search results; Over 1,000 homes in Southold

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Top guest favourite
Home in Southold
Private Waterfront Access + Hot Tub + Scenic Yard
3 bedrooms, 5 beds, 2.5 private bathrooms
1–7 Sept
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5.0 out of 5 average rating, 45 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 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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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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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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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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Cottage in Sag Harbor
Charming Cottage in Historic Sag Harbor
1 bedroom, 1 king bed, 1 bathroom
17–22 Oct
5.0 out of 5 average rating, 76 reviews
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Guest favourite
Home in Sag Harbor
Stylish house, hot tub year round
4 bedrooms, 4 beds, 2.5 bathrooms
1–6 Sept
4.91 out of 5 average rating, 109 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, 67 reviews
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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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Guest favourite
Home in Southold
Steps from the water! Southold Northfork Retreat
3 bedrooms, 5 beds, 1.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 18 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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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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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, 201 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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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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Flat in Sag Harbor
Updated apartment in historic village home
1 bedroom, 2 beds, 1 bathroom
4–9 Oct
4.98 out of 5 average rating, 240 reviews
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Holiday home in Orient
Private Vineyard w/Pool, Walk to Beach & Village
3 bedrooms, 4 beds, 3 bathrooms
1–6 Sept
5.0 out of 5 average rating, 23 reviews
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Home in Laurel
Peaceful Guesthouse
2 bedrooms, 2 beds, 1.5 bathrooms
22–27 Sept
5.0 out of 5 average rating, 37 reviews