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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
5.0 out of 5 average rating, 5 reviews, 3 bedrooms, 3 beds, 2 bathrooms
25–30 Jul
Top guest favourite
Home in Southold
Beach Front House
5.0 out of 5 average rating, 7 reviews, 4 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
Home in East Hampton
Charming Home for a Perfect Escape
5.0 out of 5 average rating, 3 reviews, 5 bedrooms, 8 beds, 3 bathrooms
27 Jul – 1 Aug
Top guest favourite
Home in Clinton
The Connecticut Cottage | Historic Modern Charm
5.0 out of 5 average rating, 16 reviews, 2 bedrooms, 2 beds, 2 bathrooms
14–19 Aug
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 Sag Harbor
9 Acre Luxury Compound in Sag Harbor NY
4.99 out of 5 average rating, 144 reviews, 7 bedrooms, 10 beds, 8.5 bathrooms
11–16 Oct
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
Top guest favourite
Home in Old Saybrook
Sunrise Beach Cottage
5.0 out of 5 average rating, 33 reviews, 2 bedrooms, 4 beds, 1 bathroom
14–19 Sept
Guest favourite
Flat in Mattituck
Mattituck 2BR: Open Layout, Deck, BBQ, Near Vines
5.0 out of 5 average rating, 5 reviews, 2 bedrooms, 2 beds, 1 bathroom
12–17 Jul
Top guest favourite
Home in Old Saybrook
Waterfront Oasis 4Bdr/2b
5.0 out of 5 average rating, 16 reviews, 4 bedrooms, 4 beds, 2 bathrooms
11–16 Oct
Guest favourite
Home in Old Lyme
Casa Swan
5.0 out of 5 average rating, 28 reviews, 3 bedrooms, 4 beds, 1 bathroom
9–14 Aug
Guest favourite
Home in Southold
Charming Ranch in North Fork
5.0 out of 5 average rating, 28 reviews, 3 bedrooms, 5 beds, 1 bathroom
15–20 Aug
Top guest favourite
Cottage in Shelter Island
Shelter Island Cottage
4.95 out of 5 average rating, 37 reviews, 5 bedrooms, 6 beds, 1.5 bathrooms
9–14 Aug
Top guest favourite
Flat in Greenport
Upscale Newly Constructed Apartment
4.96 out of 5 average rating, 171 reviews, 3 bedrooms, 6 beds, 2 bathrooms
9–14 Sept
Top guest favourite
Flat in Greenport
Newly Renovated 2-BR Apartment
4.98 out of 5 average rating, 87 reviews, 2 bedrooms, 5 beds, 1 bathroom
26–31 Jul
Top guest favourite
Home in East Hampton
East Hampton Rental w/ Pool, Moments to Amenities
5.0 out of 5 average rating, 82 reviews, 4 bedrooms, 5 beds, 3 bathrooms
1–6 Aug
Guest favourite
Home in East Marion
North Fork Coastal living in East Marion
4.88 out of 5 average rating, 99 reviews, 4 bedrooms, 4 beds, 2.5 bathrooms
21–26 Jul
Top guest favourite
Cottage in East Lyme
Beach Cottage!
5.0 out of 5 average rating, 54 reviews, 2 bedrooms, 2 beds, 1 bathroom
13–18 Sept