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Search results; Over 1,000 homes in Southold

Guest favourite
Home in Southold
Luxury Southold waterfront home, heated pool & spa
4 bedrooms, 4 beds, 4 private bathrooms
29 Aug – 5 Sept
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5.0 out of 5 average rating, 12 reviews
Superhost
Home in Montauk
Sea Ranch At Ditch Plains - Welcome To The Beach
4 bedrooms, 5 beds, 2 bathrooms
22–27 Aug
Superhost
Home in Old Saybrook
Beachfront Home with Amazing Views | 5BR Sleeps 11
5 bedrooms, 7 beds, 2 bathrooms
27 Aug – 1 Sept
New place to stay
Guest favourite
Flat in Mattituck
Mattituck 2BR: Open Layout, Deck, BBQ, Near Vines
2 bedrooms, 2 queen beds, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 7 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
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, 104 reviews
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
Home in Sag Harbor
Sag Harbor Summer House
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 10 reviews
Superhost
Home in Clinton
The Blue Mermaid
3 bedrooms, 3 beds, 2.5 bathrooms
3–8 Aug
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
Superhost
Home in Sag Harbor
Sag Harbor New Construction
7 bedrooms, 8 beds, 8 bathrooms
7–12 Aug
New place to stay
Home in East Hampton
Eauclaire Street cozy cottage
3 bedrooms, 3 beds, 2 bathrooms
2–7 Aug
New place to stay
Top guest favourite
Guest suite in East Hampton
Hamptons Dream Suite
1 bedroom, 3 beds, 1 bathroom
2–7 Aug
4.98 out of 5 average rating, 160 reviews
Top guest favourite
Cottage in Riverhead
Savor Ocean Sunsets at a Soothing Beachfront Haven
2 bedrooms, 3 beds, 1 bathroom
1–6 Oct
4.98 out of 5 average rating, 179 reviews
Superhost
Flat in Cutchogue
Cozy North Fork Hideaway
1 bedroom, 1 bed, 1 bathroom
1–6 Aug
New place to stay
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
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 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
Guest favourite
Home in Orient
Orient Point Family Waterfront Home
5 bedrooms, 9 beds, 3.5 bathrooms
30 Aug – 6 Sept
4.96 out of 5 average rating, 24 reviews