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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
Home in East Hampton
5 bedroom waterfront on Gardiner's Bay
5 bedrooms, 10 beds, 2 bathrooms
12–17 Jul
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
Guest favourite
Home in Shelter Island
New vacation house on the island with the pool
5.0 out of 5 average rating, 8 reviews, 3 bedrooms, 5 beds, 3 bathrooms
6–11 Jul
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 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 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
Room in Sag Harbor
Sag Harbor Home, Perfect for the Solo Traveler
4.96 out of 5 average rating, 248 reviews, 2 beds, 1 bathroom
8–13 Aug
Guest favourite
Home in East Marion
Waterfront Bungalow w/Private Beach on Peconic Bay
4.88 out of 5 average rating, 42 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
1–8 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
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
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
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
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
Top guest favourite
Home in Branford
Adorable Beach House on LI Sound
4.98 out of 5 average rating, 97 reviews, 1 bedroom, 2 beds, 1.5 bathrooms
16–21 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