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Search results; Over 1,000 homes in Southold

Top guest favourite
Guest suite in Southold
Comfortable Suite, a walk to the beach
1 bedroom, 1 bed, 1 private bathroom
2–7 Aug
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4.94 out of 5 average rating, 151 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
New place to stay, 5 bedrooms, 7 beds, 2 bathrooms
21–26 Aug
Guest favourite
Home in Shelter Island
New vacation house on the island with the pool
5.0 out of 5 average rating, 8 reviews, 3 bedrooms, 5 beds, 3 bathrooms
7–12 Aug
Top guest favourite
Home in East Hampton
Hamptons Beach House
5.0 out of 5 average rating, 17 reviews, 4 bedrooms, 5 beds, 3 bathrooms
22–27 Sept
Superhost
Home in Clinton
The Blue Mermaid
3 bedrooms, 3 beds, 2.5 bathrooms
3–8 Aug
Guest favourite
Flat in Mattituck
Mattituck 2BR: Open Layout, Deck, BBQ, Near Vines
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
Home in East Hampton
Eauclaire Street cozy cottage
New place to stay, 3 bedrooms, 3 beds, 2 bathrooms
2–7 Aug
Top guest favourite
Home in Sag Harbor
Sag Harbor Summer House
5.0 out of 5 average rating, 10 reviews, 3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
Guest favourite
Home in Madison
Fabulous pool in beach town!
4.95 out of 5 average rating, 22 reviews, 4 bedrooms, 4 beds, 2.5 bathrooms
21–26 Aug
Top guest favourite
Guest suite in East Hampton
Hamptons Dream Suite
4.98 out of 5 average rating, 160 reviews, 1 bedroom, 3 beds, 1 bathroom
2–7 Aug
Guest favourite
Home in Orient
Orient Point Family Waterfront Home
4.96 out of 5 average rating, 24 reviews, 5 bedrooms, 9 beds, 3.5 bathrooms
30 Aug – 6 Sept
Home in Montauk
Walk to ocean/surf break. Garden+outdoor shower.
New place to stay, 2 bedrooms, 2 beds, 1 bathroom
18–23 Aug
Top guest favourite
Home in Greenport
The North Star: Greenport Waterview Beach Getaway
4.95 out of 5 average rating, 65 reviews, 3 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
Top guest favourite
Holiday home in Hampton Bays
Hamptons house -ultra-private backyard, near beach
5.0 out of 5 average rating, 17 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
20–25 Sept
Top guest favourite
Home in Sag Harbor
Hamptons Retreat | Pool, Hot Tub, Built-in BBQ
5.0 out of 5 average rating, 8 reviews, 4 bedrooms, 5 beds, 3 bathrooms
14–19 Sept
Superhost
Home in Sag Harbor
Sag Harbor Retreat
New place to stay, 7 bedrooms, 8 beds, 8 bathrooms
7–12 Aug
Guest favourite
Home in Old Saybrook
Summertime in Old Saybrook on the Oyster River
5.0 out of 5 average rating, 8 reviews, 5 bedrooms, 6 beds, 2.5 bathrooms
9–14 Nov
Superhost
Flat in Cutchogue
Cozy North Fork Hideaway
New place to stay, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug