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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, 11 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
Flat in Southold
1BR Apartment - Beach Access - Wineries, Vineyards
1 bedroom, 1 queen bed, 1 bathroom
5–10 Jul
New place to stay
Top guest favourite
Home in Southold
NoFo Family Beach House — Walk To Private Beach
4 bedrooms, 4 beds, 2 bathrooms
13–20 Jul
5.0 out of 5 average rating, 32 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
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
Flat in Southold
Bright, Southold Studio Apt near beach & town
2 beds, 1 bathroom
12–17 Jul
4.94 out of 5 average rating, 144 reviews
Home in Southold
Waterfront North Fork Retreat • Sunset & Vineyards
4 bedrooms, 5 beds, 3 bathrooms
1–8 Jul
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
Southold Sea'renity
3 bedrooms, 5 beds, 2 bathrooms
30 Jul – 4 Aug
4.82 out of 5 average rating, 45 reviews
Top guest favourite
Home in Southold
Dockside Getaway in Southold NY
3 bedrooms, 5 beds, 3 bathrooms
2–7 Jul
4.95 out of 5 average rating, 40 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, 76 reviews
Guest favourite
Home in Peconic
Provence on the North Fork
3 bedrooms, 3 beds, 3 bathrooms
13–20 Jul
4.94 out of 5 average rating, 32 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, 6 reviews
Top guest favourite
Cottage in Greenport
3 Min Walk to Beach| 1 Mile to Town | Fam-Friendly
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 63 reviews
Superhost
Home in Southold
Sunset Cottage
3 bedrooms, 4 beds, 2.5 bathrooms
14–21 Jul
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Greenport
The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub
3 bedrooms, 3 beds, 2 bathrooms
14–19 Jul
4.96 out of 5 average rating, 51 reviews
Top guest favourite
Home in Southold
Charming Ranch in North Fork
3 bedrooms, 5 beds, 1 bathroom
18–23 Jul
5.0 out of 5 average rating, 27 reviews