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Search results; Over 1,000 homes in Southold

Top guest favourite
Guest house in Southold
Southold- Adorable 1 Bedroom Cottage
1 bedroom, 1 bed, 1 private bathroom
4–9 Oct
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4.92 out of 5 average rating, 96 reviews
Top guest favourite
Home in Sag Harbor
Sag Harbor Charming Forest Home
3 bedrooms, 4 beds, 2 bathrooms
21–26 Sept
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Home in East Marion
Bohemian Old Life Saving Station with Beach & Pool
6 bedrooms, 8 beds, 4 bathrooms
27 Sept – 2 Oct
4.97 out of 5 average rating, 114 reviews
Home in Cutchogue
Steps to Beach, Vineyards, Farm Stands & Village
3 bedrooms, 3 beds, 2 bathrooms
10–15 Sept
New place to stay
Top guest favourite
Home in Southold
Steps from the water! Fall Northfork Retreat
3 bedrooms, 5 beds, 1.5 bathrooms
10–15 Sept
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
Guest favourite
Home in Southampton
Vogue Editors Home, Featured Hamptons Mag, Elle D.
4 bedrooms, 4 beds, 7.5 bathrooms
11–16 Sept
5.0 out of 5 average rating, 5 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
Guest favourite
Home in Cutchogue
North Fork Paradise
4 bedrooms, 5 beds, 3.5 bathrooms
10–15 Sept
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Southampton
Tranquil Southampton/Sag Harbor 5 Bedroom, Pool
5 bedrooms, 5 beds, 3 bathrooms
20–25 Sept
4.98 out of 5 average rating, 51 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
Top guest favourite
Cottage in Cutchogue
Stunning waterfront modern farmhouse with dock.
4 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
4.98 out of 5 average rating, 63 reviews
Top guest favourite
Home in Greenport
The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub
3 bedrooms, 3 beds, 2 bathrooms
24–29 Sept
4.97 out of 5 average rating, 60 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
Home in Shelter Island Heights
Creekside House Shelter Island
4 bedrooms, 5 beds, 3.5 bathrooms
10–15 Sept
5.0 out of 5 average rating, 3 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
Home in Sag Harbor
Comfortable 3 bed in Sag Harbor
3 bedrooms, 3 beds, 4 bathrooms
11–16 Sept
New place to stay
Home in Greenport
Little House on Center Street
2 bedrooms, 2 queen beds, 1.5 bathrooms
10–15 Sept
New place to stay
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, 129 reviews