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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
18–23 Sept
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4.89 out of 5 average rating, 197 reviews
Superhost
Home in Clinton
The Blue Mermaid
3 bedrooms, 3 beds, 2.5 bathrooms
24–29 Jul
Top guest favourite
Flat in Mattituck
Mattituck 2BR: Open Layout, Deck, BBQ, Near Vines
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 2 beds, 1 bathroom
26–31 Jul
Home in Old Lyme
Stoneacre at Point O'Woods
2 bedrooms, 2 beds, 2 bathrooms
9–14 Aug
Top guest favourite
Home in Branford
Adorable Beach House on LI Sound
4.98 out of 5 average rating, 98 reviews, 1 bedroom, 2 beds, 1.5 bathrooms
27 Sept – 2 Oct
Guest favourite
Home in Old Saybrook
Red Bird Waterfront Home. Dock available extra!
4.94 out of 5 average rating, 35 reviews, 3 bedrooms, 3 beds, 2 bathrooms
26–31 Jul
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
17–22 Jul
Top guest favourite
Cottage in Old Lyme
The Solo Shore Cottage | Walk to Beach + Sun Porch
5.0 out of 5 average rating, 5 reviews, 2 bedrooms, 4 beds, 1 bathroom
2–7 Aug
Top guest favourite
Home in East Hampton
Hamptons Beach House
5.0 out of 5 average rating, 17 reviews, 4 bedrooms, 5 beds, 3 bathrooms
22–27 Sept
Home in Laurel
North Fork Luxury Retreat with Exceptional Comfort
New place to stay, 5 bedrooms, 5 beds, 3 bathrooms
3–8 Aug
Superhost
Flat in Mattituck
Vineyard Views: Private Patio and BBQ, Farm Access
5.0 out of 5 average rating, 3 reviews, 1 bedroom, 2 beds, 1 bathroom
19–24 Jul
Home in Sag Harbor
Sun-Filled, Custom-Designed 5-bedroom Sag Harbor
New place to stay, 5 bedrooms, 7 beds, 3 bathrooms
20–25 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
21–26 Jul
Top guest favourite
Cottage in Southampton
Towd Point Beach Cottage w heated pool
4.98 out of 5 average rating, 48 reviews, 3 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
Guest favourite
Home in Greenport
Bayview house with salt water pool & private chef
4.82 out of 5 average rating, 11 reviews, 3 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
Guest favourite
Home in Montauk
Dockside 2BR - Marina - Dining - Charter Access Un
4.96 out of 5 average rating, 28 reviews, 2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
Home in East Hampton
Tranquil Springs Cottage
5.0 out of 5 average rating, 4 reviews, 2 bedrooms, 2 beds, 1 bathroom
23–28 Aug
Top guest favourite
Home in East Marion
Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV
5.0 out of 5 average rating, 26 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
18–25 Jul
Top guest favourite
Cottage in Shelter Island
Shelter Island Cottage
4.95 out of 5 average rating, 40 reviews, 5 bedrooms, 6 beds, 1.5 bathrooms
9–14 Aug