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Search results; Over 1,000 homes in Southold

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Top guest favourite
Home in Greenport
Greenport Beachfront Home | Private Beach & Sunset
4 bedrooms, 7 beds, 2 bathrooms
18–23 Sept
5.0 out of 5 average rating, 8 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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Top guest favourite
Home in Amagansett
Ocean views, steps to beach, newly renovated home
5 bedrooms, 7 beds, 3 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 22 reviews
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Top guest favourite
Cottage in Shelter Island
Shelter Island Cottage
5 bedrooms, 6 beds, 1.5 bathrooms
20–25 Sept
4.95 out of 5 average rating, 44 reviews
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Top guest favourite
Home in East Marion
POOL + Beach Oasis! Winter deals 2+ nights!
5 bedrooms, 5 beds, 3 bathrooms
4–9 Oct
4.97 out of 5 average rating, 30 reviews
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Luxe
Villa in East Hampton
Luxe|Pool|Games|Movie|HotTub|Firepit|MegaChess
3 bedrooms, 3 beds, 3.5 bathrooms
30 Sept – 5 Oct
4.99 out of 5 average rating, 70 reviews
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Guest favourite
Home in East Hampton
4 BD w/ Heated Pool in E Hampton, Fully Furnished
4 bedrooms, 4 beds, 3 bathrooms
12–18 Oct
4.89 out of 5 average rating, 133 reviews
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Superhost
Home in East Marion
Bungalow by the Bay
2 bedrooms, 2 queen beds, 1.5 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Home in Clinton
The Connecticut Cottage | Historic Modern Charm
2 bedrooms, 2 beds, 2 bathrooms
30 Sept – 5 Oct
4.97 out of 5 average rating, 31 reviews
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Bungalow in Old Lyme
Your Coastal Getaway Awaits in Old Lyme, CT!
3 bedrooms, 3 queen beds, 1.5 bathrooms
27 Sept – 2 Oct
New place to stay
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Superhost
Home in Old Saybrook
Oceanside retreat Sleeps 8 3bds~3bths
3 bedrooms, 5 beds, 3 bathrooms
18–23 Sept
New place to stay
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Home in Wainscott
Private, Charming, Lovely Farmhouse, 1 mi to ocean
3 bedrooms, 4 beds, 3 bathrooms
19–24 Oct
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Cottage in Sag Harbor
Hamptons Waterfront Getaway – Stylish & Serene
2 bedrooms, 2 queen beds, 2 bathrooms
25–30 Oct
5.0 out of 5 average rating, 18 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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Top guest favourite
Home in Southampton
Tranquil Southampton/Sag Harbor 5 Bedroom, Pool
5 bedrooms, 5 beds, 3 bathrooms
15–20 Oct
4.98 out of 5 average rating, 51 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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Top guest favourite
Home in Southold
Country Beach Home!
4 bedrooms, 8 beds, 2.5 bathrooms
20–25 Sept
4.96 out of 5 average rating, 23 reviews
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Home in Shelter Island
Waterfront Retreat | Spa Pool, Sauna & Dock
3 bedrooms, 3 beds, 3.5 bathrooms
21–26 Sept
New place to stay