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Search results; Over 1,000 homes in Southold

Guest favourite
Home in Southold
Luxury Southold waterfront home, heated pool & spa
4 bedrooms, 4 beds, 4 private bathrooms
29 Aug – 5 Sept
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5.0 out of 5 average rating, 12 reviews
Guest favourite
Home in Southold
Charming Ranch in North Fork
5.0 out of 5 average rating, 28 reviews, 3 bedrooms, 5 beds, 1 bathroom
15–20 Aug
Guest favourite
Home in Southold
Family and Dog Friendly Private Beach
5.0 out of 5 average rating, 5 reviews, 3 bedrooms, 3 beds, 2 bathrooms
25–30 Jul
Top guest favourite
Home in Southold
NoFo Family Beach House — Walk To Private Beach
5.0 out of 5 average rating, 32 reviews, 4 bedrooms, 4 beds, 2 bathrooms
16–23 Aug
Top guest favourite
Home in Southold
Private Waterfront Access + Hot Tub + Scenic Yard
5.0 out of 5 average rating, 45 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
5–11 Jul
Top guest favourite
Cottage in Southold
Adorable Cottage
4.95 out of 5 average rating, 78 reviews, 2 bedrooms, 4 beds, 1 bathroom
13–18 Sept
Top guest favourite
Home in Southold
Luxury by the Sea!!
4.94 out of 5 average rating, 53 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
30 Aug – 4 Sept
Guest favourite
Cottage in Southold
Cozy Cottage on the Great Pond near beach.
4.9 out of 5 average rating, 196 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
27 Jul – 1 Aug
Guest favourite
Home in Southold
Shelter Bay Cove Waterfront Escape
4.97 out of 5 average rating, 30 reviews, 3 bedrooms, 3 beds, 2 bathrooms
5–10 Sept
Guest favourite
Townhouse in Greenport
Renovated Townhouse, Walk to All
4.96 out of 5 average rating, 134 reviews, 3 bedrooms, 5 beds, 1.5 bathrooms
11–16 Jul
Guest favourite
Home in Southold
Le Petit Cottage, Southold, NY
4.91 out of 5 average rating, 80 reviews, 2 bedrooms, 3 beds, 1 bathroom
5–10 Sept
Guest favourite
Home in Southold
Southold waterfront 4 bed, pool open til October
4.9 out of 5 average rating, 77 reviews, 4 bedrooms, 5 beds, 3 bathrooms
24–29 Jul
Top guest favourite
Home in Southold
Country Beach Home!
4.94 out of 5 average rating, 17 reviews, 4 bedrooms, 8 beds, 2.5 bathrooms
30 Aug – 4 Sept
Top guest favourite
Home in Southold
Beach Front House
5.0 out of 5 average rating, 7 reviews, 4 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
Home in Southold
Luxury North Fork Beachfront Escape Near Greenport
4.93 out of 5 average rating, 15 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
2–7 Aug
Guest favourite
Guest house in Southold
Southold- Adorable 1 Bedroom Cottage
4.9 out of 5 average rating, 82 reviews, 1 bedroom, 1 bed, 1 bathroom
23–28 Aug
Guest favourite
Cottage in Southold
Bordeaux meets Côte d’Azur—1763 Historic Farmhouse
4.92 out of 5 average rating, 66 reviews, 3 bedrooms, 4 beds, 2 bathrooms
8–15 Jul
Guest favourite
Flat in Southold
Kenney's Beach Loft - Vineyards, Horton Lighthouse
4.83 out of 5 average rating, 6 reviews, 1 bedroom, 1 bed, 1 bathroom
20–25 Jul
Guest favourite
Home in Southold
Southold Escape With Large Pool on Wine Trail
5.0 out of 5 average rating, 19 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
19–24 Jul