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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, 203 reviews
Top guest favourite
Home in Sag Harbor
Sag Harbor Charming Forest Home
3 bedrooms, 4 beds, 2 bathrooms
11–16 Sept
5.0 out of 5 average rating, 21 reviews
Guest favourite
Home in Greenport
Walk to Beach or to Town …
3 bedrooms, 4 beds, 2.5 bathrooms
10–15 Sept
4.88 out of 5 average rating, 43 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
Home in Cutchogue
Steps to Beach, Vineyards, Farm Stands & Village
3 bedrooms, 3 beds, 2 bathrooms
10–15 Sept
New place to stay
Home in Sag Harbor
Striking Waterfront 3 Bedroom on Sag Harbor Cove
3 bedrooms, 4 beds, 3 bathrooms
20–25 Sept
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 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
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
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
Rooms in Greenport
Chestnut View Room own private bathroom
2 bedrooms, 3 queen beds, No bathroom
11–16 Oct
5.0 out of 5 average rating, 102 reviews
Top guest favourite
Home in Southampton
Tranquil Southampton/Sag Harbor 5 Bedroom, Pool
5 bedrooms, 5 beds, 3 bathrooms
18–23 Sept
4.98 out of 5 average rating, 51 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
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
Guest favourite
Home in Greenport
Aqua Vista
2 bedrooms, 3 beds, 1 bathroom
12–17 Oct
4.95 out of 5 average rating, 270 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, 129 reviews
Guest favourite
Villa in Shelter Island
Superb Shelter Island 4 bed Designer with a Pool
3 bedrooms, 4 beds, 3 bathrooms
11–16 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Southold
Waterfront, Dock, Boat Ramp, Hot Tub & Beaches
4 bedrooms, 8 beds, 3 bathrooms
10–15 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Shelter Island Heights
Laid Back Relaxation
3 bedrooms, 4 beds, 2 bathrooms
10–15 Sept
5.0 out of 5 average rating, 23 reviews