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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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4.9 out of 5 average rating, 196 reviews
Guest favourite
Home in Southold
Family and Dog Friendly Private Beach
3 bedrooms, 3 queen beds, 2 bathrooms
25–30 Jul
5.0 out of 5 average rating, 5 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
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
Top guest favourite
Home in Clinton
The Connecticut Cottage | Historic Modern Charm
2 bedrooms, 2 beds, 2 bathrooms
14–19 Aug
5.0 out of 5 average rating, 16 reviews
Superhost
Home in Montauk
Sea Ranch At Ditch Plains - Welcome To The Beach
4 bedrooms, 5 beds, 2 bathrooms
6–11 Dec
Top guest favourite
Home in Westbrook
Home Away From Home
3 bedrooms, 6 beds, 2 bathrooms
20–25 Aug
4.99 out of 5 average rating, 84 reviews
Top guest favourite
Room in Sag Harbor
Sag Harbor Home, Perfect for the Solo Traveler
2 beds, 1 bathroom
18–23 Jul
4.96 out of 5 average rating, 248 reviews
Top guest favourite
Home in Old Saybrook
Sunrise Beach Cottage
2 bedrooms, 4 beds, 1 bathroom
14–19 Sept
5.0 out of 5 average rating, 33 reviews
Top guest favourite
Home in Old Saybrook
Waterfront Oasis 4Bdr/2b
4 bedrooms, 4 beds, 2 bathrooms
11–16 Oct
5.0 out of 5 average rating, 16 reviews
Guest favourite
Flat in Mattituck
Mattituck 2BR: Open Layout, Deck, BBQ, Near Vines
2 bedrooms, 2 queen beds, 1 bathroom
12–17 Jul
5.0 out of 5 average rating, 5 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
Guest favourite
Home in Southold
Charming Ranch in North Fork
3 bedrooms, 5 beds, 1 bathroom
15–20 Aug
5.0 out of 5 average rating, 28 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
Flat in Greenport
Upscale Newly Constructed Apartment
3 bedrooms, 6 beds, 2 bathrooms
9–14 Sept
4.96 out of 5 average rating, 171 reviews
Top guest favourite
Flat in Greenport
Newly Renovated 2-BR Apartment
2 bedrooms, 5 beds, 1 bathroom
26–31 Jul
4.98 out of 5 average rating, 87 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
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
Family Friendly Island Home
4 bedrooms, 5 beds, 2 bathrooms
13–18 Jul
4.93 out of 5 average rating, 83 reviews