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Search results; Over 1,000 homes in Southold

Guest favourite
Home in Southold
Shelter Bay Cove Waterfront Escape
3 bedrooms, 3 beds, 2 private bathrooms
5–10 Sept
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4.97 out of 5 average rating, 30 reviews
Guest favourite
Home in Southold
Charming Ranch in North Fork
3 bedrooms, 5 beds, 1 bathroom
27 Jul – 1 Aug
5.0 out of 5 average rating, 28 reviews
Flat in Southold
Kenney's Beach Loft - Vineyards, Horton Lighthouse
1 bedroom, 1 queen bed, 1 bathroom
20–25 Jul
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Southold
Luxury by the Sea!!
3 bedrooms, 4 beds, 2.5 bathrooms
30 Aug – 4 Sept
4.94 out of 5 average rating, 53 reviews
Guest favourite
Home in Southold
Family and Dog Friendly Private Beach
3 bedrooms, 3 queen beds, 2 bathrooms
25–30 Jul
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Southold
NoFo Family Beach House — Walk To Private Beach
4 bedrooms, 4 beds, 2 bathrooms
16–23 Aug
5.0 out of 5 average rating, 32 reviews
Top guest favourite
Home in Southold
Private Waterfront Access + Hot Tub + Scenic Yard
3 bedrooms, 5 beds, 2.5 bathrooms
5–11 Jul
5.0 out of 5 average rating, 45 reviews
Guest favourite
Home in Southold
Southold waterfront 4 bed, pool open til October
4 bedrooms, 5 beds, 3 bathrooms
24–29 Jul
4.9 out of 5 average rating, 77 reviews
Guest favourite
Cottage in Southold
Cozy Cottage on the Great Pond near beach.
2 bedrooms, 3 beds, 1.5 bathrooms
27 Jul – 1 Aug
4.9 out of 5 average rating, 196 reviews
Guest favourite
Cottage in Southold
Bordeaux meets Côte d’Azur—1763 Historic Farmhouse
3 bedrooms, 4 beds, 2 bathrooms
8–15 Jul
4.92 out of 5 average rating, 66 reviews
Top guest favourite
Cottage in Southold
Adorable Cottage
2 bedrooms, 4 queen beds, 1 bathroom
13–18 Sept
4.95 out of 5 average rating, 77 reviews
Top guest favourite
Home in Southold
Country Beach Home!
4 bedrooms, 8 beds, 2.5 bathrooms
30 Aug – 4 Sept
4.94 out of 5 average rating, 16 reviews
Top guest favourite
Home in Southold
Private Waterfront home with Dock!
4 bedrooms, 5 beds, 2.5 bathrooms
8–13 Jul
5.0 out of 5 average rating, 18 reviews
Guest favourite
Home in Southold
Le Petit Cottage, Southold, NY
2 bedrooms, 3 beds, 1 bathroom
5–10 Sept
4.91 out of 5 average rating, 79 reviews
Flat in Southold
1BR Apartment - Beach Access - Wineries, Vineyards
1 bedroom, 1 queen bed, 1 bathroom
5–10 Jul
New place to stay
Guest favourite
Guest house in Southold
Southold- Adorable 1 Bedroom Cottage
1 bedroom, 1 queen bed, 1 bathroom
23–28 Aug
4.9 out of 5 average rating, 80 reviews
Guest favourite
Home in Southold
Southold Sea'renity
3 bedrooms, 5 beds, 2 bathrooms
30 Jul – 4 Aug
4.82 out of 5 average rating, 45 reviews
Home in Southold
Luxury North Fork Beachfront Escape Near Greenport
3 bedrooms, 4 beds, 2.5 bathrooms
2–7 Aug
4.93 out of 5 average rating, 15 reviews
Top guest favourite
Home in Southold
Beach Front House
4 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
5.0 out of 5 average rating, 7 reviews