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
27 Jul – 1 Aug
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4.9 out of 5 average rating, 196 reviews
Flat in Southold
1BR Apartment - Beach Access - Wineries, Vineyards
New place to stay, 1 bedroom, 1 bed, 1 bathroom
5–10 Jul
Flat in Southold
Kenney's Beach Loft - Vineyards, Horton Lighthouse
5.0 out of 5 average rating, 4 reviews, 1 bedroom, 1 bed, 1 bathroom
20–25 Jul
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
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
13–20 Jul
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
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
Flat in Southold
Bright, Southold Studio Apt near beach & town
4.94 out of 5 average rating, 144 reviews, 2 beds, 1 bathroom
12–17 Jul
Home in Southold
Waterfront North Fork Retreat • Sunset & Vineyards
4 bedrooms, 5 beds, 3 bathrooms
1–8 Jul
Guest favourite
Home in Southold
Southold Sea'renity
4.82 out of 5 average rating, 45 reviews, 3 bedrooms, 5 beds, 2 bathrooms
30 Jul – 4 Aug
Guest favourite
Home in Peconic
Provence on the North Fork
4.94 out of 5 average rating, 32 reviews, 3 bedrooms, 3 beds, 3 bathrooms
13–20 Jul
Top guest favourite
Home in Southold
Dockside Getaway in Southold NY
4.95 out of 5 average rating, 40 reviews, 3 bedrooms, 5 beds, 3 bathrooms
3–8 Jul
Top guest favourite
Cottage in Southold
Adorable Cottage
4.95 out of 5 average rating, 77 reviews, 2 bedrooms, 4 beds, 1 bathroom
13–18 Sept
Superhost
Home in Southold
Sunset Cottage
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
14–21 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
Top 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
18–23 Jul
Guest favourite
Home in Southold
Peconic Pearl Cottage
5.0 out of 5 average rating, 5 reviews, 4 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
Top guest favourite
Home in Greenport
The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub
4.96 out of 5 average rating, 51 reviews, 3 bedrooms, 3 beds, 2 bathrooms
14–19 Jul
Guest favourite
Home in Southold
Waterfront Beach House with Plunge Pool & Hot Tub
4.97 out of 5 average rating, 39 reviews, 4 bedrooms, 7 beds, 4.5 bathrooms
19–26 Jul