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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
27 Jul – 1 Aug
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4.89 out of 5 average rating, 197 reviews
Top guest favourite
Cottage in Shelter Island
Shelter Island Cottage
5 bedrooms, 6 beds, 1.5 bathrooms
9–14 Aug
4.95 out of 5 average rating, 37 reviews
Top guest favourite
Home in Greenport
The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub
3 bedrooms, 3 beds, 2 bathrooms
19–24 Jul
4.96 out of 5 average rating, 52 reviews
Guest favourite
Home in East Marion
Charming North Fork escape by the beach
3 bedrooms, 4 beds, 2 bathrooms
8–15 Sept
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Home in East Hampton
East Hampton Rental w/ Pool, Moments to Amenities
4 bedrooms, 5 beds, 3 bathrooms
1–6 Aug
5.0 out of 5 average rating, 82 reviews
Top guest favourite
Home in East Hampton
Elegant Springs Retreat (New Construction)
4 bedrooms, 3.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 5 reviews
Home in East Hampton
Charming Home for a Perfect Escape
5 bedrooms, 8 beds, 3 bathrooms
27 Jul – 1 Aug
5.0 out of 5 average rating, 3 reviews
Home in Shelter Island
Captain Don’s Paradise
3 bedrooms, 4 beds, 1.5 bathrooms
3–8 Aug
4.92 out of 5 average rating, 13 reviews
Guest favourite
Home in Shelter Island
New vacation house on the island with the pool
3 bedrooms, 5 beds, 3 bathrooms
8–13 Jul
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Old Lyme
Casa Swan
3 bedrooms, 4 beds, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 28 reviews
Top guest favourite
Home in East Marion
POOL + Beach Oasis! Winter deals 2+ nights!
5 bedrooms, 5 beds, 3 bathrooms
4–9 Oct
4.97 out of 5 average rating, 29 reviews
Top guest favourite
Home in Southold
Beach Front House
4 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in East Marion
North Fork Coastal living in East Marion
4 bedrooms, 4 beds, 2.5 bathrooms
21–26 Jul
4.88 out of 5 average rating, 99 reviews
Top guest favourite
Home in Shelter Island
Surf Scoter Cottage Shelter Island
4 bedrooms, 4 beds, 2 bathrooms
23–28 Jul
4.91 out of 5 average rating, 93 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, 63 reviews
Guest favourite
Holiday home in Orient
Private Vineyard w/Pool, Walk to Beach & Village
3 bedrooms, 4 beds, 3 bathrooms
17–23 Aug
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Home in Sag Harbor
Sag Harbor Chic Mid-Century Retreat
3 bedrooms, 4 beds, 2 bathrooms
9–14 Aug
4.99 out of 5 average rating, 76 reviews
Home in Amagansett
Unit 211: Cottage | Ocean View | Striper
2 bedrooms, 1 bathroom
20–25 Sept
Home in Shelter Island Heights
Creekside House Shelter Island
4 bedrooms, 5 beds, 3.5 bathrooms
13–20 Jul