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Search results; Over 1,000 homes in Southold

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Guest favourite
Home in Southold
Luxury Southold waterfront home, heated pool & spa
4 bedrooms, 4 beds, 4 private bathrooms
1–8 Oct
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5.0 out of 5 average rating, 13 reviews
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Home in Water Mill
Cozy 5-Bed House in The Hamptons, NY
4 bedrooms, 5 beds, 4 bathrooms
1–6 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, 8.5 bathrooms
11–16 Oct
4.99 out of 5 average rating, 148 reviews
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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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Home in East Hampton
Remarkable East Hampton Getaway with Pool
3 bedrooms, 3 beds, 3 bathrooms
1–6 Oct
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Home in Sag Harbor
Striking Waterfront 3 Bedroom on Sag Harbor Cove
3 bedrooms, 4 beds, 3 bathrooms
1–6 Oct
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Top guest favourite
Home in Clinton
The Connecticut Cottage | Historic Modern Charm
2 bedrooms, 2 beds, 2 bathrooms
1–6 Oct
4.97 out of 5 average rating, 31 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, 40 reviews
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Top guest favourite
Guest suite in Southold
Comfortable Suite, a walk to the beach
1 bedroom, 1 king bed, 1 bathroom
3–8 Oct
4.94 out of 5 average rating, 159 reviews
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Guest favourite
Home in Westbrook
Cottage on the beach
3 bedrooms, 3 beds, 1 bathroom
19–24 Oct
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
Cottage in Old Saybrook
Beautiful View Cottage
2 bedrooms, 3 beds, 1 bathroom
1–6 Oct
4.98 out of 5 average rating, 169 reviews
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Luxe
Villa in East Hampton
Luxe|Pool|Games|Movie|HotTub|Firepit|MegaChess
3 bedrooms, 3 beds, 3.5 bathrooms
1–6 Oct
4.99 out of 5 average rating, 70 reviews
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Top guest favourite
Flat in Sag Harbor
Updated apartment in historic village home
1 bedroom, 2 beds, 1 bathroom
26–31 Oct
4.98 out of 5 average rating, 242 reviews
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Top guest favourite
Cottage in Old Saybrook
The Cottage
1 bedroom, 2 beds, 1 bathroom
6–11 Nov
4.75 out of 5 average rating, 261 reviews
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Top guest favourite
Home in Sagaponack
Amazing Home close to Everything -
5 bedrooms, 7 beds, 4 bathrooms
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, 2.5 bathrooms
4–9 Oct
4.89 out of 5 average rating, 44 reviews
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Top guest favourite
Room in Shelter Island
Casual Island Getaway - Walk to the Beach
1 queen bed, 1 bathroom
4–9 Oct
4.93 out of 5 average rating, 162 reviews
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Guest favourite
Home in Peconic
Provence on the North Fork
3 bedrooms, 3 beds, 3 bathrooms
1–8 Oct
4.95 out of 5 average rating, 37 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