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Search results; Over 1,000 homes in Southold

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Home in Southold
Shelter Bay Cove Waterfront Escape
3 bedrooms, 3 beds, 2 private bathrooms
13–18 Oct
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4.91 out of 5 average rating, 32 reviews
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Home in East Hampton
East Hamptons Modern 8 Bedroom New Construction
8 bedrooms, 8 beds, 6 bathrooms
1–6 Oct
5.0 out of 5 average rating, 4 reviews
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Guest favourite
Home in Old Saybrook
Old Saybrook on the Oyster River
5 bedrooms, 6 beds, 2.5 bathrooms
11–16 Oct
5.0 out of 5 average rating, 14 reviews
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Superhost
Home in Old Saybrook
Beachfront Home with Amazing Views | 5BR Sleeps 11
5 bedrooms, 7 beds, 2 bathrooms
12–17 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
1–6 Oct
4.97 out of 5 average rating, 31 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, 2.5 bathrooms
24–29 Oct
4.98 out of 5 average rating, 171 reviews
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Luxe
Villa in East Hampton
Luxe|Pool|Games|Movie|HotTub|Firepit|MegaChess
3 bedrooms, 3 beds, 3.5 bathrooms
1–6 Oct
4.99 out of 5 average rating, 70 reviews
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Guest favourite
Home in Greenport
Walk to Beach or to Town …
3 bedrooms, 4 beds, 2.5 bathrooms
4–9 Oct
4.89 out of 5 average rating, 44 reviews
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Featured hotel
Hotel in Greenport
Oyster Estate, Classic king
1 bedroom, 1 king bed, 1 bathroom
4–9 Oct
New place to stay
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Superhost
Home in Old Lyme
Connecticut Beach Home
4 bedrooms, 6 beds, 2 bathrooms
10–15 Oct
New place to stay
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Guest favourite
Home in East Hampton
Chic & Spacious Designer Home, Heated Pool/Spa
3 bedrooms, 4 beds, 2.5 bathrooms
17–22 Oct
4.97 out of 5 average rating, 33 reviews
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Guest favourite
Home in Old Lyme
Casa Swan
3 bedrooms, 4 beds, 1 bathroom
5–10 Oct
5.0 out of 5 average rating, 34 reviews
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Top guest favourite
Home in East Hampton
Charming Home for a Perfect Escape
5 bedrooms, 7 beds, 3 bathrooms
17–22 Oct
4.93 out of 5 average rating, 15 reviews
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Top guest favourite
Cottage in Shelter Island
Shelter Island Cottage
5 bedrooms, 6 beds, 1.5 bathrooms
1–6 Oct
4.96 out of 5 average rating, 45 reviews
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Home in Cutchogue
Steps to Beach, Vineyards, Farm Stands & Village
3 bedrooms, 3 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Cottage in Old Saybrook
Charming Old Saybrook Cottage < 1 Mi to Beach
4 bedrooms, 4 beds, 2 bathrooms
27 Oct – 1 Nov
4.88 out of 5 average rating, 41 reviews
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Top guest favourite
Cottage in Guilford
"Red House on the Knoll" at Indian Cove
3 bedrooms, 5 beds, 2.5 bathrooms
2–7 Oct
4.99 out of 5 average rating, 179 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
Luxury by the Sea!!
3 bedrooms, 4 beds, 2.5 bathrooms
3–8 Oct
4.95 out of 5 average rating, 59 reviews