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Search results; Over 1,000 homes in Southold

Guest favourite
Cottage in Southold
Cozy Cottage on the Great Pond near beach.
2 bedrooms, 3 beds, 1.5 private bathrooms
11–16 Oct
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4.89 out of 5 average rating, 197 reviews
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
Superhost
Villa in Southampton
US Golf Open & Ocean View Retreat, Walk to Event
4.83 out of 5 average rating, 6 reviews, 4 bedrooms, 4 beds, 3.5 bathrooms
5–10 Oct
Home in East Hampton
The Springs House
5.0 out of 5 average rating, 4 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
18–23 Aug
Guest favourite
Flat in Greenport
Greenport Harbor Apartment
4.96 out of 5 average rating, 97 reviews, 3 bedrooms, 4 beds, 2 bathrooms
2–7 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
Top guest favourite
Home in East Lyme
Charming Cottage in Private Oak Grove Beach
4.97 out of 5 average rating, 73 reviews, 3 bedrooms, 6 beds, 1 bathroom
8–13 Nov
Home in Southold
The Shorecrest Beach House
5.0 out of 5 average rating, 4 reviews, 4 bedrooms, 6 beds, 2 bathrooms
14–19 Oct
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
Superhost
Home in Clinton
The Blue Mermaid
3 bedrooms, 3 beds, 2.5 bathrooms
1–6 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
1–6 Aug
Top guest favourite
Home in Westbrook
Home Away From Home
4.99 out of 5 average rating, 84 reviews, 3 bedrooms, 6 beds, 2 bathrooms
20–25 Aug
Home in East Hampton
Eauclaire Street cozy cottage
New place to stay, 3 bedrooms, 3 beds, 2 bathrooms
2–7 Aug
Guest favourite
Home in Sag Harbor
Hamptons Retreat | Pool, Hot Tub, Built-in BBQ
5.0 out of 5 average rating, 7 reviews, 4 bedrooms, 5 beds, 3 bathrooms
17–22 Aug
Top guest favourite
Home in East Lyme
Walk to the beach at Black Point, Niantic, Ct
4.98 out of 5 average rating, 167 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
2–8 Aug
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
Home in Cutchogue
Soundwood Retreat. Get away from the noise.
4 bedrooms, 5 beds, 3 bathrooms
31 May – 5 Jun
Top guest favourite
Flat in Greenport
Greenport Condo with Stunning Views & Beach Access
5.0 out of 5 average rating, 24 reviews, 2 bedrooms, 4 beds, 2 bathrooms
30 Aug – 4 Sept
Top guest favourite
Home in Shelter Island
Surf Scoter Cottage Shelter Island
4.92 out of 5 average rating, 95 reviews, 4 bedrooms, 4 beds, 2 bathrooms
14–19 Aug