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Search results; Over 1,000 homes in Southold

Guest favourite
Flat in Southold
Bright, Southold Studio Apt near beach & town
Studio, 2 beds, 1 private bathroom
2–7 Aug
,
4.95 out of 5 average rating, 147 reviews
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
Home in Branford
Adorable Beach House on LI Sound
1 bedroom, 2 beds, 1.5 bathrooms
27 Sept – 2 Oct
4.98 out of 5 average rating, 100 reviews
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
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
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
Home in Shelter Island Heights
Creekside House Shelter Island
4 bedrooms, 5 beds, 3.5 bathrooms
5–12 Aug
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
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, 13 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 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
Superhost
Villa in Southampton
US Golf Open & Ocean View Retreat, Walk to Event
4 bedrooms, 4 beds, 3.5 bathrooms
21–26 Sept
4.83 out of 5 average rating, 6 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
Top guest favourite
Home in Greenport
The North Star: Greenport Waterview Beach Getaway
3 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
4.95 out of 5 average rating, 65 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 Sag Harbor
Sag Harbor Chic Mid-Century Retreat
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.99 out of 5 average rating, 77 reviews
Top guest favourite
Flat in Greenport
Upscale Newly Constructed Apartment
3 bedrooms, 6 beds, 2 bathrooms
24–29 Jul
4.96 out of 5 average rating, 173 reviews
Guest favourite
Home in Clinton
Historic Coastal Home • Marsh Views • Pet-Friendly
4 bedrooms, 4 beds, 3.5 bathrooms
9–14 Aug
5.0 out of 5 average rating, 12 reviews