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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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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 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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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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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 East Hampton
Amagansett Farmhouse Retreat - Pool Through Oct.
4 bedrooms, 6 beds, 3 bathrooms
19–24 Oct
4.99 out of 5 average rating, 111 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
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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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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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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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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Top guest favourite
Cottage in East Lyme
Beach Cottage!
2 bedrooms, 2 queen beds, 1 bathroom
25–30 Oct
5.0 out of 5 average rating, 64 reviews
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Superhost
Home in Old Lyme
Connecticut Beach Home
Business host
10–15 Oct
New place to stay
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Home in Orient
Brand new 4 bedrm 4.5 bath home with pool & beach
4 bedrooms, 5 beds, 4.5 bathrooms
6–11 Oct
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Home in Sag Harbor
Sag Harbor Village Gem
3 bedrooms, 3 beds, 2.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 102 reviews
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Top guest favourite
Home in Old Saybrook
Waterfront Oasis 4Bdr/2b
4 bedrooms, 4 beds, 2 bathrooms
19–24 Oct
5.0 out of 5 average rating, 18 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