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Search results; Over 1,000 homes in Southold

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Top guest favourite
Guest house in Southold
Southold- Adorable 1 Bedroom Cottage
1 bedroom, 1 bed, 1 private bathroom
4–9 Oct
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4.92 out of 5 average rating, 96 reviews
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Home in Shelter Island
NEW RENTAL: MAGICAL SHELTER ISLAND RETREAT
5 bedrooms, 8 beds
30 Sept – 7 Oct
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Guest favourite
Home in Peconic
Provence on the North Fork
3 bedrooms, 3 beds
20–27 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
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
25–30 Sept
5.0 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
25–30 Oct
5.0 out of 5 average rating, 40 reviews
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Guest favourite
Holiday home in Orient
Private Vineyard w/Pool, Walk to Beach & Village
3 bedrooms, 4 beds
20–25 Sept
5.0 out of 5 average rating, 24 reviews
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Top guest favourite
Rooms in Greenport
Chestnut View Room own private bathroom
2 bedrooms, 3 queen beds
10–15 Nov
4.99 out of 5 average rating, 105 reviews
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Home in Cutchogue
Steps to Beach, Vineyards, Farm Stands & Village
3 bedrooms, 3 beds
20–25 Sept
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Cottage in Shelter Island
Shelter Island Cottage
5 bedrooms, 6 beds
20–25 Sept
4.95 out of 5 average rating, 44 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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Top guest favourite
Home in Old Saybrook
Best of both worlds!
3 bedrooms, 4 beds
12–17 Oct
4.92 out of 5 average rating, 119 reviews
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Top guest favourite
Home in East Marion
POOL + Beach Oasis! Winter deals 2+ nights!
5 bedrooms, 5 beds
4–9 Oct
4.97 out of 5 average rating, 30 reviews
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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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Top guest favourite
Home in Shelter Island
Shelter Island Home with Large Yard And Pool
3 bedrooms, 6 beds
21–28 Sept
5.0 out of 5 average rating, 14 reviews
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Top guest favourite
Cottage in East Lyme
Beach Cottage!
2 bedrooms, 2 queen beds
25–30 Oct
5.0 out of 5 average rating, 64 reviews
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Guest favourite
Home in Orient
Luxury Escape - Saltwater Pool
4 bedrooms, 7 beds
20–25 Sept
5.0 out of 5 average rating, 19 reviews
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Top guest favourite
Cottage in Sag Harbor
Hamptons Waterfront Getaway – Stylish & Serene
2 bedrooms, 2 queen beds
25–30 Oct
5.0 out of 5 average rating, 18 reviews
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Top guest favourite
Cottage in Shelter Island
3 Bedroom Cottage Gem
3 bedrooms, 4 beds
26 Sept – 1 Oct
4.97 out of 5 average rating, 131 reviews