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Search results; Over 1,000 homes in Southold

Guest favourite
Home in Southampton
Vogue Editors Home, Featured Hamptons Mag, Elle D.
4 bedrooms, 4 beds, 7.5 bathrooms
11–16 Oct
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Southold
Steps from the water! Fall Northfork Retreat
3 bedrooms, 5 beds, 1.5 bathrooms
13–18 Oct
5.0 out of 5 average rating, 20 reviews
Top guest favourite
Home in Cutchogue
Sunny Harbor Suite
1 bedroom, 1 queen bed, 1 bathroom
3–8 Nov
4.96 out of 5 average rating, 25 reviews
Home in Cutchogue
Steps to Beach, Vineyards, Farm Stands & Village
3 bedrooms, 3 beds, 2 bathrooms
14–19 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Greenport
The North Star: Greenport Waterview Beach Getaway
3 bedrooms, 4 beds, 2 bathrooms
26–31 Oct
4.96 out of 5 average rating, 69 reviews
Superhost
Home in Shelter Island Heights
*New Shelter Island 5Br|Heated Pool+Crescent Beach
5 bedrooms, 6 beds, 5 bathrooms
15–20 Sept
Top guest favourite
Home in Southold
Waterfront, Dock, Boat Ramp, Hot Tub & Beaches
4 bedrooms, 8 beds, 3 bathrooms
14–19 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Cottage in Shelter Island
3 Bedroom Cottage Gem
3 bedrooms, 4 beds, 2.5 bathrooms
26 Sept – 1 Oct
4.97 out of 5 average rating, 131 reviews
Top guest favourite
Home in Southold
Luxury by the Sea!!
3 bedrooms, 4 beds, 2.5 bathrooms
16–21 Sept
4.95 out of 5 average rating, 58 reviews
Top guest favourite
Home in Southold
Beautiful waterfront 3 bedroom home in Southold
3 bedrooms, 5 beds, 2 bathrooms
14–19 Sept
5.0 out of 5 average rating, 32 reviews
Top guest favourite
Home in Greenport
The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub
3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.97 out of 5 average rating, 60 reviews
Top guest favourite
Cottage in Sag Harbor
Hamptons Waterfront Getaway – Stylish & Serene
2 bedrooms, 2 queen beds, 2 bathrooms
25–30 Oct
5.0 out of 5 average rating, 18 reviews
Home in Shelter Island
Waterfront Retreat | Spa Pool, Sauna & Dock
3 bedrooms, 3 beds, 3.5 bathrooms
21–26 Sept
New place to stay
Top guest favourite
Cottage in Sag Harbor
Luxury Gem At The Heart of Sag Harbor Village
2 bedrooms, 2 beds, 1.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 71 reviews
Guest favourite
Home in Greenport
Greenport Beachfront Home | Private Beach & Sunset
4 bedrooms, 7 beds, 2 bathrooms
17–22 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Flat in Greenport
Upscale Newly Constructed Apartment
3 bedrooms, 6 beds, 2 bathrooms
29 Sept – 4 Oct
4.96 out of 5 average rating, 179 reviews
Top guest favourite
Place to stay in Cutchogue
Sunset Suite - walk to vineyards, beaches, & more
1 bedroom, 1 king bed, 1 bathroom
4–9 Oct
4.98 out of 5 average rating, 206 reviews
Home in Greenport
Greenport Getaway
3 bedrooms, 3 beds, 2 bathrooms
27 Oct – 1 Nov