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Search results; Over 1,000 homes in Southold

Guest favourite
Home in Southold
Beach house @ NoFo
3 bedrooms, 5 beds, 2 private bathrooms
31 Aug – 6 Sept
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4.93 out of 5 average rating, 84 reviews
Home in Greenport
Greenport Beachfront Home | Private Beach & Sunset
4 bedrooms, 7 beds, 2 bathrooms
2–7 Aug
Top guest favourite
Home in Old Saybrook
Hot Tub & Firepit•Sunsets & Beach Walk | Fireplace
3 bedrooms, 6 beds, 1.5 bathrooms
26–31 Aug
5.0 out of 5 average rating, 99 reviews
Top guest favourite
Home in Branford
Adorable Beach House on LI Sound
1 bedroom, 2 beds, 1.5 bathrooms
27 Sept – 2 Oct
4.98 out of 5 average rating, 105 reviews
Top guest favourite
Home in East Hampton
Hamptons Beach House
4 bedrooms, 5 beds, 3 bathrooms
22–27 Sept
5.0 out of 5 average rating, 17 reviews
Home in Southold
The Shorecrest Beach House
4 bedrooms, 6 beds, 2 bathrooms
19–24 Oct
5.0 out of 5 average rating, 4 reviews
Home in Amagansett
Lazy Point Gem w access to Private Beach
3 bedrooms, 3 beds, 1 bathroom
9–14 Aug
New place to stay
Guest favourite
Home in Old Saybrook
Summertime in Old Saybrook on the Oyster River
5 bedrooms, 6 beds, 2.5 bathrooms
9–14 Nov
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Cottage in East Lyme
Beach Cottage!
2 bedrooms, 2 queen beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 57 reviews
Top guest favourite
Home in Greenport
The North Star: Greenport Waterview Beach Getaway
3 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
4.95 out of 5 average rating, 65 reviews
Home in Shelter Island Heights
Creekside House Shelter Island
4 bedrooms, 5 beds, 3.5 bathrooms
5–12 Aug
Guest favourite
Home in Shelter Island
Captain Don’s Paradise
3 bedrooms, 4 beds, 1.5 bathrooms
9–14 Aug
4.92 out of 5 average rating, 13 reviews
Top guest favourite
Holiday home in Hampton Bays
Hamptons house -ultra-private backyard, near beach
3 bedrooms, 4 beds, 2.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Home in Sag Harbor
Sag Harbor Summer House
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 11 reviews
Superhost
Home in Clinton
The Blue Mermaid
3 bedrooms, 3 beds, 2.5 bathrooms
3–8 Aug
Top guest favourite
Cottage in Sag Harbor
Charming Cottage in Historic Sag Harbor
1 bedroom, 1 king bed, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 69 reviews
Guest favourite
Home in Shelter Island
New vacation house on the island with the pool
3 bedrooms, 5 beds, 3 bathrooms
7–12 Aug
5.0 out of 5 average rating, 8 reviews
Home in East Hampton
5 bedroom waterfront on Gardiner's Bay
5 bedrooms, 10 beds, 2 bathrooms
29 Aug – 3 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Madison
Fabulous pool in beach town!
4 bedrooms, 4 beds, 2.5 bathrooms
21–26 Aug
4.95 out of 5 average rating, 22 reviews