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Search results; Over 1,000 homes in Southold

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Guest favourite
Flat in Southold
Bright, Southold Studio Apt near beach & town
Studio, 2 beds, 1 private bathroom
4–9 Oct
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4.95 out of 5 average rating, 159 reviews
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Featured hotel
Hotel in Greenport
Oyster Estate, Signature King
1 bedroom, 1 king bed
1–6 Oct
New place to stay
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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 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, 172 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 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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Superhost
Home in Old Saybrook
Oceanside retreat Sleeps 8 3bds~3bths
3 bedrooms, 5 beds
1–6 Oct
New place to stay
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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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Top guest favourite
Home in East Hampton
Charming Home for a Perfect Escape
5 bedrooms, 7 beds
6–11 Oct
4.93 out of 5 average rating, 15 reviews
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Superhost
Home in East Marion
Bungalow by the Bay
2 bedrooms, 2 queen beds
1–6 Oct
5.0 out of 5 average rating, 4 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 Clinton
The Connecticut Cottage | Historic Modern Charm
2 bedrooms, 2 beds
11–16 Oct
4.97 out of 5 average rating, 32 reviews
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Top guest favourite
Home in Greenport
Bayview house with salt water pool & private chef
3 bedrooms, 4 beds
4–9 Oct
4.91 out of 5 average rating, 22 reviews
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Luxe
Villa in East Hampton
Luxe|Pool|Games|Movie|HotTub|Firepit|MegaChess
3 bedrooms, 3 beds
12–17 Oct
4.97 out of 5 average rating, 71 reviews
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Top guest favourite
Home in Old Saybrook
Year Round Beach House in Old Saybrook, CT.- Pets
4 bedrooms, 7 beds
11–16 Oct
4.97 out of 5 average rating, 146 reviews
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Top guest favourite
Home in East Hampton
Amagansett Farmhouse Retreat - Pool Through Oct.
4 bedrooms, 6 beds
19–24 Oct
4.99 out of 5 average rating, 111 reviews
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Superhost
Home in Sag Harbor
Harrison House | Heated Pool, Walk to Village
5 bedrooms, 6 queen beds
5–10 Oct
New place to stay
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Guest favourite
Villa in Greenport
Greenport Villa with Pool
5 bedrooms, 6 beds
4–9 Oct
4.97 out of 5 average rating, 35 reviews
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Home in Shelter Island
Waterfront Retreat | Spa Pool, Sauna & Dock
3 bedrooms, 3 beds
1–6 Oct
New place to stay