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Search results; Over 1,000 homes in Southold

Guest favourite
Home in Southold
Southold waterfront 4 bed, pool open til October
4 bedrooms, 5 beds, 3 private bathrooms
11–16 Sept
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4.91 out of 5 average rating, 87 reviews
Top guest favourite
Home in East Marion
Bohemian Old Life Saving Station with Beach & Pool
6 bedrooms, 8 beds, 4 bathrooms
9–16 Sept
4.97 out of 5 average rating, 114 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
Home in Cutchogue
Steps to Beach, Vineyards, Farm Stands & Village
3 bedrooms, 3 beds, 2 bathrooms
9–14 Sept
New place to stay
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
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
9–14 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
Top guest favourite
Home in Southold
Steps from the water! Fall Northfork Retreat
3 bedrooms, 5 beds, 1.5 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 20 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 Greenport
The North Star: Greenport Waterview Beach Getaway
3 bedrooms, 4 beds, 2 bathrooms
19–24 Oct
4.96 out of 5 average rating, 69 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, 59 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
Home in Sag Harbor
Striking Waterfront 3 Bedroom on Sag Harbor Cove
3 bedrooms, 4 beds, 3 bathrooms
20–25 Sept
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
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
Home in Sag Harbor
Sag Harbor Summer House
3 bedrooms, 4 beds, 2 bathrooms
9–14 Sept
4.95 out of 5 average rating, 19 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