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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, 194 reviews
Flat in Southold
Kenney's Beach Loft - Vineyards, Horton Lighthouse
1 bedroom, 1 queen bed, 1 bathroom
5–10 Jul
New place to stay
Home in Southold
Waterfront North Fork Retreat • Sunset & Vineyards
4 bedrooms, 5 beds, 3 bathrooms
1–8 Jul
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
Top guest favourite
Guest suite in Southold
Comfortable Suite, a walk to the beach
1 bedroom, 1 king bed, 1 bathroom
5–10 Jul
4.94 out of 5 average rating, 146 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, 52 reviews
Home in Southold
Luxury North Fork Beachfront Escape Near Greenport
3 bedrooms, 4 beds, 2.5 bathrooms
5–11 Jul
4.93 out of 5 average rating, 15 reviews
Guest favourite
Home in Southold
Southold Sea'renity
3 bedrooms, 5 beds, 2 bathrooms
1–7 Jul
4.82 out of 5 average rating, 45 reviews
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
Private Waterfront Access + Hot Tub + Scenic Yard
3 bedrooms, 5 beds, 2.5 bathrooms
1–7 Jul
5.0 out of 5 average rating, 45 reviews
Home in Southold
Family and Dog Friendly Private Beach
3 bedrooms, 3 queen beds, 2 bathrooms
25 Jul – 1 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Guest house in Southold
Southold- Adorable 1 Bedroom Cottage
1 bedroom, 1 queen bed, 1 bathroom
16–21 Jul
4.9 out of 5 average rating, 79 reviews
Guest favourite
Home in Southold
Southold Escape With Large Pool on Wine Trail
3 bedrooms, 3 double beds, 2.5 bathrooms
19–24 Jul
5.0 out of 5 average rating, 19 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
Family & dog-friendly getaway!
4 bedrooms, 5 beds, 2 bathrooms
5–10 Jul
Guest favourite
Home in Southold
North Fork Waterfront Escape · Sunset Views
3 bedrooms, 3 queen beds, 2 bathrooms
5–10 Sept
4.97 out of 5 average rating, 30 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, 143 reviews
Guest favourite
Home in Southold
Beach Front House
4 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
5.0 out of 5 average rating, 5 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