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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
3–8 Oct
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4.94 out of 5 average rating, 159 reviews
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Featured hotel
Hotel in Greenport
Oyster Estate, Classic king
1 bedroom, 1 king bed
4–9 Oct
New place to stay
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Guest favourite
Home in Sag Harbor
9 Acre Luxury Compound in Sag Harbor NY
7 bedrooms, 10 beds
11–16 Oct
4.99 out of 5 average rating, 148 reviews
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Home in East Hampton
East Hampton Beach House | Private Beach
4 bedrooms, 5 beds
5–10 Oct
5.0 out of 5 average rating, 3 reviews
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Home in East Hampton
Remarkable East Hampton Getaway with Pool
3 bedrooms, 3 beds
1–6 Oct
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Home in Water Mill
Cozy 5-Bed House in The Hamptons, NY
4 bedrooms, 5 beds
1–6 Oct
New place to stay
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Top guest favourite
Cottage in Shelter Island
Shelter Island Cottage
5 bedrooms, 6 beds
1–6 Oct
4.96 out of 5 average rating, 45 reviews
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Guest favourite
Home in Orient
Orient Point Family Waterfront Home
5 bedrooms, 9 beds
3–8 Oct
4.96 out of 5 average rating, 27 reviews
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Guest favourite
Home in Orient
Luxury Escape - Saltwater Pool
4 bedrooms, 7 beds
1–6 Oct
5.0 out of 5 average rating, 19 reviews
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Luxe
Villa in East Hampton
Luxe|Pool|Games|Movie|HotTub|Firepit|MegaChess
3 bedrooms, 3 beds
1–6 Oct
4.99 out of 5 average rating, 70 reviews
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Guest favourite
Home in Southampton
Vogue Editors Home, Featured Hamptons Mag, Elle D.
4 bedrooms, 4 beds
11–16 Oct
5.0 out of 5 average rating, 7 reviews
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Luxe
Home in Montauk
Montauk modern 7-bedroom Heated Pool & hot tub
7 bedrooms, 10 beds
25–30 Oct
5.0 out of 5 average rating, 40 reviews
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Guest favourite
Home in East Marion
Waterfront 3BR Home w/Private Beach on Peconic Bay
3 bedrooms, 4 beds
1–8 Oct
4.89 out of 5 average rating, 44 reviews
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Top guest favourite
Home in Montauk
Oceanfront Home Downtown Montauk
3 bedrooms, 6 beds
25–30 Oct
4.91 out of 5 average rating, 35 reviews
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Home in Shelter Island
Waterfront Retreat | Spa Pool, Sauna & Dock
3 bedrooms, 3 beds
1–6 Oct
New place to stay
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Home in Cutchogue
Steps to Beach, Vineyards, Farm Stands & Village
3 bedrooms, 3 beds
1–6 Oct
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
1–6 Oct
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Top guest favourite
Home in Sagaponack
Amazing Home close to Everything -
5 bedrooms, 7 beds
4–9 Oct
4.94 out of 5 average rating, 334 reviews
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Guest favourite
Home in Greenport
Walk to Beach or to Town …
3 bedrooms, 4 beds
4–9 Oct
4.89 out of 5 average rating, 44 reviews