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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
8–13 Sept
New place to stay
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Room in Greenport
Direct Beach Access | Free Breakfast. Pool. Bar.
1 queen bed
7–12 Sept
New place to stay
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Superhost
Cottage in Shelter Island
3 Bedroom Cottage Gem
3 bedrooms, 4 beds
6–11 Sept
4.97 out of 5 average rating, 129 reviews
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Home in Westbrook
Cottage on the beach
3 bedrooms, 3 beds
13–18 Sept
New place to stay
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Home in Greenport
Greenport Beachfront Home | Private Beach & Sunset
4 bedrooms, 7 beds
2–7 Sept
5.0 out of 5 average rating, 4 reviews
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Guest favourite
Home in Old Lyme
Make the "BlueBird" your new summer vacation home!
2 bedrooms, 2 beds
28 Sept – 3 Oct
5.0 out of 5 average rating, 5 reviews
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Home in Shelter Island
Waterfront Retreat | Spa Pool, Sauna & Dock
3 bedrooms, 3 beds
8–13 Sept
New place to stay
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Top guest favourite
Home in Old Saybrook
Cozy beach side home Chalker Beach Old Saybrook
3 bedrooms, 4 beds
8–13 Sept
5.0 out of 5 average rating, 8 reviews
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Cottage in Guilford
"Red House on the Knoll" at Indian Cove
3 bedrooms, 5 beds
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
7–14 Sept
5.0 out of 5 average rating, 3 reviews
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Superhost
Home in Old Saybrook
Beachfront Home with Amazing Views | 5BR Sleeps 11
5 bedrooms, 7 beds
13–18 Sept
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Cottage in Shelter Island
Shelter Island Cottage
5 bedrooms, 6 beds
6–11 Sept
4.95 out of 5 average rating, 43 reviews
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Home in Sag Harbor
Sag Harbor Summer House
3 bedrooms, 4 beds
7–12 Sept
5.0 out of 5 average rating, 15 reviews
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Home in Old Saybrook
Hot Tub & Firepit•Sunsets & Beach Walk | Fireplace
3 bedrooms, 6 beds
20–25 Sept
5.0 out of 5 average rating, 103 reviews
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Home in East Hampton
Hamptons Beach House
4 bedrooms, 5 beds
22–27 Sept
5.0 out of 5 average rating, 17 reviews
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Top guest favourite
Home in East Hampton
East Hampton Escape | Pool & Private Beach Access
4 bedrooms, 4 beds
7–12 Sept
5.0 out of 5 average rating, 24 reviews
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Guest favourite
Home in Sag Harbor
Barefoot Bliss | Quiet Family Retreat Heated Pool
3 bedrooms, 4 beds
13–18 Sept
4.91 out of 5 average rating, 201 reviews
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Top guest favourite
Home in Shelter Island Heights
Laid Back Relaxation
3 bedrooms, 4 beds
7–12 Sept
5.0 out of 5 average rating, 22 reviews