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Search results; Over 1,000 homes in Southold

Superhost
Home in Clinton
The Blue Mermaid
3 bedrooms, 3 beds, 2.5 bathrooms
24–29 Jul
Home in Laurel
North Fork Luxury Retreat with Exceptional Comfort
5 bedrooms, 5 beds, 3 bathrooms
3–8 Aug
New place to stay
Top guest favourite
Cottage in Shelter Island
Shelter Island Cottage
5 bedrooms, 6 beds, 1.5 bathrooms
6–11 Sept
4.95 out of 5 average rating, 40 reviews
Guest favourite
Home in East Marion
North Fork Coastal living in East Marion
4 bedrooms, 4 beds, 2.5 bathrooms
28 Jul – 2 Aug
4.88 out of 5 average rating, 99 reviews
Home in Shelter Island Heights
Creekside House Shelter Island
4 bedrooms, 5 beds, 3.5 bathrooms
5–12 Aug
Top guest favourite
Home in East Hampton
Hamptons Beach House
4 bedrooms, 5 beds, 3 bathrooms
22–27 Sept
5.0 out of 5 average rating, 17 reviews
Home in Sag Harbor
Charming house in Sag Harbor.
3 bedrooms, 3 beds, 2 bathrooms
14–19 Sept
5.0 out of 5 average rating, 10 reviews
Guest favourite
Cottage in Old Lyme
The Solo Shore Cottage | Walk to Beach + Sun Porch
2 bedrooms, 4 beds, 1 bathroom
18–23 Aug
5.0 out of 5 average rating, 6 reviews
Superhost
Flat in Mattituck
Vineyard Views: Private Patio and BBQ, Farm Access
1 bedroom, 2 queen beds, 1 bathroom
26–31 Jul
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Old Lyme
Casa Swan
3 bedrooms, 4 beds, 1 bathroom
8–13 Aug
5.0 out of 5 average rating, 28 reviews
Guest favourite
Home in Shelter Island
Shelter Island House: Peaceful Retreat
3 bedrooms, 3 beds, 2 bathrooms
6–11 Aug
5.0 out of 5 average rating, 28 reviews
Guest favourite
Home in East Hampton
Charming Home for a Perfect Escape
5 bedrooms, 8 beds, 3 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in East Marion
Charming North Fork escape by the beach
3 bedrooms, 4 beds, 2 bathrooms
8–15 Sept
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Cottage in Southampton
Towd Point Beach Cottage w heated pool
3 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
4.98 out of 5 average rating, 48 reviews
Top guest favourite
Home in Old Saybrook
Desirable Fenwood Beach-walk to beach-dogs allowed
3 bedrooms, 3 beds, 1.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Home in Clinton
“11:11” 🙏 Updated Stylish Retreat 🌊 2 Mi To Beach
4 bedrooms, 5 beds, 2 bathrooms
26–31 Jul
4.95 out of 5 average rating, 85 reviews
Top guest favourite
Home in Old Saybrook
Best of both worlds!
3 bedrooms, 4 beds, 2 bathrooms
24–29 Aug
4.92 out of 5 average rating, 111 reviews
Top guest favourite
Room in Sag Harbor
Sag Harbor Home, Perfect for the Solo Traveler
2 beds, 1 bathroom
8–13 Aug
4.96 out of 5 average rating, 254 reviews