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Search results; Over 1,000 homes in Southold

Guest favourite
Guest house in Southold
Southold- Adorable 1 Bedroom Cottage
1 bedroom, 1 bed, 1 private bathroom
12–17 Oct
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4.91 out of 5 average rating, 87 reviews
Guest favourite
Home in Shelter Island
New vacation house on the island with the pool
3 bedrooms, 5 beds, 3 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 8 reviews
Superhost
Home in Montauk
Sea Ranch At Ditch Plains - Welcome To The Beach
4 bedrooms, 5 beds, 2 bathrooms
31 Aug – 6 Sept
Top guest favourite
Guest house in Shelter Island
Bayfront 1BR/2BR detached guesthouse with pool
1 bedroom, 2 beds, 1 bathroom
7–12 Sept
4.99 out of 5 average rating, 76 reviews
Guest favourite
Home in Peconic
Provence on the North Fork
3 bedrooms, 3 beds, 3 bathrooms
30 Aug – 6 Sept
4.94 out of 5 average rating, 34 reviews
Top guest favourite
Cottage in Shelter Island
Shelter Island Cottage
5 bedrooms, 6 beds, 1.5 bathrooms
6–11 Sept
4.95 out of 5 average rating, 41 reviews
Guest favourite
Home in Mattituck
Lakehouse Getaway North Fork
3 bedrooms, 5 beds, 2 bathrooms
16–21 Aug
5.0 out of 5 average rating, 46 reviews
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
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
Rooms in East Hampton
Two Lovely Private Rooms
2 bedrooms, 2 queen beds, 1 bathroom
7–12 Sept
4.95 out of 5 average rating, 22 reviews
Top guest favourite
Home in Old Lyme
Casa Swan
3 bedrooms, 4 beds, 1 bathroom
24–29 Aug
5.0 out of 5 average rating, 31 reviews
Guest favourite
Home in East Marion
North Fork Coastal living in East Marion
4 bedrooms, 4 beds, 2.5 bathrooms
18–23 Aug
4.88 out of 5 average rating, 99 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
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 Wainscott
Charming Wainscott Cottage
2 bedrooms, 3 beds, 1.5 bathrooms
31 Aug – 5 Sept
5.0 out of 5 average rating, 5 reviews
Home in East Marion
The Gathering House | North Fork Retreat
4 bedrooms, 5 beds, 3.5 bathrooms
31 Aug – 5 Sept
New place to stay
Top guest favourite
Home in Old Saybrook
Desirable Fenwood Beach-walk to beach-dogs allowed
3 bedrooms, 3 beds, 1.5 bathrooms
22–27 Sept
5.0 out of 5 average rating, 15 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, 59 reviews
Top guest favourite
Home in East Hampton
Hamptons Beach House
4 bedrooms, 5 beds, 3 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 17 reviews