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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
20–27 Sept
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5.0 out of 5 average rating, 13 reviews
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Home in Shelter Island
NEW RENTAL: MAGICAL SHELTER ISLAND RETREAT
5 bedrooms, 8 beds, 4.5 bathrooms
30 Sept – 7 Oct
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Home in Peconic
Provence on the North Fork
3 bedrooms, 3 beds, 3 bathrooms
19–26 Sept
4.95 out of 5 average rating, 37 reviews
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Top guest favourite
Home in East Hampton
Beautiful east hampton cottage by the bay
4 bedrooms, 2 queen beds, 2.5 bathrooms
5–10 Oct
5.0 out of 5 average rating, 16 reviews
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Top guest favourite
Home in East Hampton
Designer East Hampton with Bay Views + Pool
4 bedrooms, 4 beds, 3.5 bathrooms
25–30 Sept
5.0 out of 5 average rating, 31 reviews
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Holiday home in Orient
Private Vineyard w/Pool, Walk to Beach & Village
3 bedrooms, 4 beds, 3 bathrooms
19–24 Sept
5.0 out of 5 average rating, 24 reviews
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Home in Greenport
Aqua Vista
2 bedrooms, 3 beds, 1 bathroom
12–17 Oct
4.95 out of 5 average rating, 271 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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Home in Cutchogue
Steps to Beach, Vineyards, Farm Stands & Village
3 bedrooms, 3 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 3 reviews
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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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Cottage in Old Saybrook
The Cottage
1 bedroom, 2 beds, 1 bathroom
6–11 Nov
4.75 out of 5 average rating, 260 reviews
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Home in East Hampton
East Hampton Beach House | Private Beach
4 bedrooms, 5 beds, 3 bathrooms
20–25 Sept
5.0 out of 5 average rating, 3 reviews
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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 Shelter Island
Shelter Island Home with Large Yard And Pool
3 bedrooms, 6 beds, 2 bathrooms
19–26 Sept
5.0 out of 5 average rating, 14 reviews
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Home in East Hampton
Remarkable East Hampton Getaway with Pool
3 bedrooms, 3 beds, 3 bathrooms
23–28 Sept
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Home in Sag Harbor
Sag Harbor home away from home
2 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
4.98 out of 5 average rating, 237 reviews
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Home in Greenport
Greenport Beachfront Home | Private Beach & Sunset
4 bedrooms, 7 beds, 2 bathrooms
19–24 Sept
5.0 out of 5 average rating, 8 reviews
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Home in Old Saybrook
Best of both worlds!
3 bedrooms, 4 beds, 2 bathrooms
12–17 Oct
4.92 out of 5 average rating, 119 reviews
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Home in Wainscott
Charming Wainscott Cottage
2 bedrooms, 3 beds, 1.5 bathrooms
19–24 Sept
5.0 out of 5 average rating, 11 reviews