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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
11–16 Oct
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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
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
21–26 Jul
Home in Laurel
North Fork Luxury Retreat with Exceptional Comfort
New place to stay, 5 bedrooms, 5 beds, 3 bathrooms
3–8 Aug
Guest favourite
Home in Shelter Island
Shelter Island House: Peaceful Retreat
5.0 out of 5 average rating, 29 reviews, 3 bedrooms, 3 beds, 2 bathrooms
6–11 Aug
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
6–11 Sept
Home in East Hampton
East Hamptons 3BR Private +Den Private Entrance
New place to stay, 3 bedrooms, 2 beds, 2 bathrooms
29 Jul – 3 Aug
Guest favourite
Cottage in Old Lyme
The Solo Shore Cottage | Walk to Beach + Sun Porch
5.0 out of 5 average rating, 6 reviews, 2 bedrooms, 4 beds, 1 bathroom
18–23 Aug
Guest favourite
Home in East Marion
Charming North Fork escape by the beach
5.0 out of 5 average rating, 12 reviews, 3 bedrooms, 4 beds, 2 bathrooms
8–15 Sept
Guest favourite
Home in Madison
Fabulous pool in beach town!
4.95 out of 5 average rating, 22 reviews, 4 bedrooms, 4 beds, 2.5 bathrooms
21–26 Aug
Guest favourite
Home in East Hampton
Charming Home for a Perfect Escape
5.0 out of 5 average rating, 5 reviews, 5 bedrooms, 8 beds, 3 bathrooms
30 Aug – 4 Sept
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
Top guest favourite
Home in Old Saybrook
Desirable Fenwood Beach-walk to beach-dogs allowed
5.0 out of 5 average rating, 13 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
13–18 Sept
Top guest favourite
Flat in Old Saybrook
Charming Center of it All Location
4.99 out of 5 average rating, 68 reviews, 2 bedrooms, 2 beds, 1 bathroom
1–6 Aug
Guest favourite
Home in Orient
Newly renovated cottage steps to Jitney and shops
5.0 out of 5 average rating, 8 reviews, 2 bedrooms, 3 beds, 1 bathroom
27 Aug – 1 Sept
Top guest favourite
Home in Sag Harbor
Sag Harbor Summer House
5.0 out of 5 average rating, 8 reviews, 3 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
Home in Sag Harbor
Charming house in Sag Harbor.
5.0 out of 5 average rating, 10 reviews, 3 bedrooms, 3 beds, 2 bathrooms
14–19 Sept
Home in East Hampton
5 bedroom waterfront on Gardiner's Bay
5.0 out of 5 average rating, 3 reviews, 5 bedrooms, 10 beds, 2 bathrooms
29 Aug – 3 Sept
Top guest favourite
Home in Clinton
“11:11” 🙏 Updated Stylish Retreat 🌊 2 Mi To Beach
4.95 out of 5 average rating, 85 reviews, 4 bedrooms, 5 beds, 2 bathrooms
26–31 Jul