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Search results; Over 1,000 homes in Southold

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Top guest favourite
Room in Southold
Vine + Sand Southold, NY's Newest B&B-Room 3
1 bedroom, 1 bed, 1 private bathroom
1–6 Oct
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5.0 out of 5 average rating, 21 reviews
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Featured hotel
Hotel in Greenport
Oyster Estate, Classic king
1 bedroom, 1 king bed, 1 bathroom
4–9 Oct
New place to stay
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Top guest favourite
Cottage in Shelter Island
Shelter Island Cottage
5 bedrooms, 6 beds, 1.5 bathrooms
1–6 Oct
4.96 out of 5 average rating, 45 reviews
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Home in East Hampton
East Hampton Beach House | Private Beach
4 bedrooms, 5 beds, 3 bathrooms
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, 3 bathrooms
1–6 Oct
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Guest favourite
Home in Southampton
Vogue Editors Home, Featured Hamptons Mag, Elle D.
4 bedrooms, 4 beds, 7.5 bathrooms
11–16 Oct
5.0 out of 5 average rating, 7 reviews
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Guest favourite
Home in Sag Harbor
9 Acre Luxury Compound in Sag Harbor NY
7 bedrooms, 10 beds, 8.5 bathrooms
11–16 Oct
4.99 out of 5 average rating, 148 reviews
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Home in Cutchogue
Steps to Beach, Vineyards, Farm Stands & Village
3 bedrooms, 3 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Holiday home in Orient
Private Vineyard w/Pool, Walk to Beach & Village
3 bedrooms, 4 beds, 3 bathrooms
1–6 Oct
5.0 out of 5 average rating, 24 reviews
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Luxe
Home in Montauk
Montauk modern 7-bedroom Heated Pool & hot tub
7 bedrooms, 10 beds, 5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 41 reviews
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Guest favourite
Home in Orient
Luxury Escape - Saltwater Pool
4 bedrooms, 7 beds, 2.5 bathrooms
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, 3.5 bathrooms
9–14 Oct
4.99 out of 5 average rating, 70 reviews
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Top guest favourite
Home in Clinton
The Connecticut Cottage | Historic Modern Charm
2 bedrooms, 2 beds, 2 bathrooms
11–16 Oct
4.97 out of 5 average rating, 32 reviews
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Top guest favourite
Home in Montauk
Oceanfront Home Downtown Montauk
3 bedrooms, 6 beds, 1.5 bathrooms
25–30 Oct
4.91 out of 5 average rating, 35 reviews
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Guest favourite
Home in Orient
Orient Point Family Waterfront Home
5 bedrooms, 9 beds, 3.5 bathrooms
3–8 Oct
4.96 out of 5 average rating, 27 reviews
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Home in Shelter Island
Waterfront Retreat | Spa Pool, Sauna & Dock
3 bedrooms, 3 beds, 3.5 bathrooms
1–6 Oct
New place to stay
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Bungalow in Old Lyme
Your Coastal Getaway Awaits in Old Lyme, CT!
3 bedrooms, 3 queen beds, 1.5 bathrooms
4–9 Oct
4.67 out of 5 average rating, 3 reviews
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Guest favourite
Home in East Hampton
The Springs House
4 bedrooms, 5 beds, 2.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 8 reviews
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Superhost
Home in Old Lyme
Connecticut Beach Home
4 bedrooms, 6 beds, 2 bathrooms
10–15 Oct
New place to stay