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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
Home in Shelter Island Heights
Creekside House Shelter Island
4 bedrooms, 5 beds, 3.5 bathrooms
5–11 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
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
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
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
Guest favourite
Home in Orient
Luxury Escape - Saltwater Pool
5.0 out of 5 average rating, 15 reviews, 4 bedrooms, 7 beds, 2.5 bathrooms
16–23 Aug
Home in East Hampton
The Springs House
5.0 out of 5 average rating, 4 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
11–18 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
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 East Lyme
Charming Cottage in Private Oak Grove Beach
4.97 out of 5 average rating, 72 reviews, 3 bedrooms, 6 beds, 1 bathroom
8–13 Nov
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 East Hampton
5 bedroom waterfront on Gardiner's Bay
5.0 out of 5 average rating, 3 reviews, 5 bedrooms, 10 beds, 2 bathrooms
29 Aug – 3 Sept
Guest favourite
Home in Sag Harbor
Hamptons Retreat | Pool, Hot Tub, Built-in BBQ
5.0 out of 5 average rating, 6 reviews, 4 bedrooms, 5 beds, 3 bathrooms
17–22 Aug
Home in East Hampton
Tranquil Springs Cottage
5.0 out of 5 average rating, 4 reviews, 2 bedrooms, 2 beds, 1 bathroom
23–28 Aug
Superhost
Tent in East Hampton
Safari Tent Glamping,S5-CedarPt, East Hampton, NY
4.86 out of 5 average rating, 56 reviews, 1 bedroom, 3 beds, 1 bathroom
1–6 Aug
Top guest favourite
Home in Old Saybrook
Desirable Fenwood Beach-walk to beach-dogs allowed
5.0 out of 5 average rating, 13 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
13–18 Sept
Superhost
Home in Clinton
The Blue Mermaid
3 bedrooms, 3 beds, 2.5 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