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Search results; Over 1,000 homes in Southold

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Top guest favourite
Guest suite in Southold
Comfortable Suite, a walk to the beach
1 bedroom, 1 bed, 1 private bathroom
27 Sept – 2 Oct
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4.94 out of 5 average rating, 156 reviews
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Home in East Hampton
East Hampton Beach House | Private Beach
4 bedrooms, 5 beds, 3 bathrooms
8–13 Sept
New place to stay
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Home in Greenport
Greenport Beachfront Home | Private Beach & Sunset
4 bedrooms, 7 beds, 2 bathrooms
6–11 Sept
5.0 out of 5 average rating, 4 reviews
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Superhost
Cottage in Shelter Island
3 Bedroom Cottage Gem
3 bedrooms, 4 beds, 2.5 bathrooms
6–11 Sept
4.97 out of 5 average rating, 129 reviews
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Home in East Lyme
Charming Cottage in Private Oak Grove Beach
3 bedrooms, 6 beds, 1 bathroom
8–13 Nov
4.97 out of 5 average rating, 79 reviews
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Home in Old Saybrook
Cozy beach side home Chalker Beach Old Saybrook
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 8 reviews
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Home in Westbrook
Cottage on the beach
3 bedrooms, 3 beds, 1 bathroom
13–18 Sept
New place to stay
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Home in Old Lyme
Make the "BlueBird" your new summer vacation home!
2 bedrooms, 2 beds, 2 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 5 reviews
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Home in Sag Harbor
Sag Harbor Summer House
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 15 reviews
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Cottage in Guilford
"Red House on the Knoll" at Indian Cove
3 bedrooms, 5 beds, 2.5 bathrooms
18–23 Sept
4.99 out of 5 average rating, 177 reviews
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Home in Shelter Island Heights
Creekside House Shelter Island
4 bedrooms, 5 beds, 3.5 bathrooms
7–14 Sept
5.0 out of 5 average rating, 3 reviews
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Room in Greenport
Direct Beach Access | Free Breakfast. Pool. Bar.
1 queen bed, 1 bathroom
7–12 Sept
New place to stay
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Home in Old Lyme
Casa Swan
3 bedrooms, 4 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 32 reviews
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Home in Clinton
The Connecticut Cottage | Historic Modern Charm
2 bedrooms, 2 beds, 2 bathrooms
18–23 Sept
4.96 out of 5 average rating, 25 reviews
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Home in Old Saybrook
Year Round Beach House in Old Saybrook, CT.- Pets
4 bedrooms, 7 beds, 2 bathrooms
9–14 Sept
4.97 out of 5 average rating, 146 reviews
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Home in East Hampton
East Hampton Escape | Pool & Private Beach Access
4 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 24 reviews
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Home in Old Saybrook
Hot Tub & Firepit•Sunsets & Beach Walk | Fireplace
3 bedrooms, 6 beds, 1.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 103 reviews
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Home in East Hampton
Serene East Hampton Escape - Stars Forest Sauna
4 bedrooms, 5 beds, 5.5 bathrooms
12–17 Oct
4.99 out of 5 average rating, 153 reviews
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Cottage in Shelter Island
Shelter Island Cottage
5 bedrooms, 6 beds, 1.5 bathrooms
6–11 Sept
4.95 out of 5 average rating, 43 reviews