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Search results; Over 1,000 homes in Southold

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Guest favourite
Cottage in Southold
Bordeaux meets Côte d’Azur—1763 Historic Farmhouse
3 bedrooms, 4 beds, 2 private bathrooms
26–31 Oct
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4.92 out of 5 average rating, 71 reviews
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Featured hotel
Hotel in Greenport
Oyster Estate, Classic king
1 bedroom, 1 king bed
4–9 Oct
New place to stay
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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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Home in East Hampton
East Hamptons Modern 8 Bedroom New Construction
8 bedrooms, 8 beds
1–6 Oct
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Home in Clinton
The Connecticut Cottage | Historic Modern Charm
2 bedrooms, 2 beds
1–6 Oct
4.97 out of 5 average rating, 32 reviews
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Top guest favourite
Cottage in Shelter Island
Shelter Island Cottage
5 bedrooms, 6 beds
1–6 Oct
4.96 out of 5 average rating, 45 reviews
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Superhost
Home in Old Saybrook
Oceanside retreat Sleeps 8 3bds~3bths
3 bedrooms, 5 beds
4–9 Oct
New place to stay
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Home in Southold
The Shorecrest Beach House
4 bedrooms, 6 beds
19–24 Oct
5.0 out of 5 average rating, 4 reviews
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Guest favourite
Home in Greenport
Walk to Beach or to Town …
3 bedrooms, 4 beds
4–9 Oct
4.89 out of 5 average rating, 44 reviews
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Top guest favourite
Home in Southold
Country Beach Home!
4 bedrooms, 8 beds
6–11 Oct
4.96 out of 5 average rating, 24 reviews
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Top guest favourite
Home in East Lyme
Walk to the beach at Black Point, Niantic, Ct
3 bedrooms, 4 beds
24–29 Oct
4.98 out of 5 average rating, 171 reviews
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Guest favourite
Home in Old Saybrook
Old Saybrook on the Oyster River
5 bedrooms, 6 beds
11–16 Oct
5.0 out of 5 average rating, 14 reviews
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Home in Greenport
Brand New Build! Greenport Gem w/ Yard & Patio
3 bedrooms, 3 beds
12–17 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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Bungalow in Old Lyme
Your Coastal Getaway Awaits in Old Lyme, CT!
3 bedrooms, 3 queen beds
4–9 Oct
New place to stay
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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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Top guest favourite
Home in Montauk
Oceanfront Home Downtown Montauk
3 bedrooms, 6 beds
25–30 Oct
4.91 out of 5 average rating, 35 reviews
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Superhost
Home in Old Saybrook
Beachfront Home with Amazing Views | 5BR Sleeps 11
5 bedrooms, 7 beds
12–17 Oct
5.0 out of 5 average rating, 3 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