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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 Greenport
Beach Block Hideaway
2 bedrooms, 4 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 22 reviews
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
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
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, 147 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
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
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
Top guest favourite
Home in Southold
Dockside Getaway in Southold NY
3 bedrooms, 5 beds, 3 bathrooms
4–9 Jul
4.95 out of 5 average rating, 40 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
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
Guest favourite
Home in Southold
Peconic Pearl Cottage
4 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 5 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
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
Home in Southold
Beach Front House
4 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
5.0 out of 5 average rating, 7 reviews
Guest favourite
Room in Southold
Cozy guest room - quiet getaway - wine country
1 queen bed, 1 bathroom
27 Oct – 1 Nov
4.96 out of 5 average rating, 150 reviews
Guest favourite
Apartment in Greenport
Beachside Waterview 2Br Condo w/ Pool in Greenport
2 bedrooms, 3 beds, 2 bathrooms
5–10 Jul
4.9 out of 5 average rating, 155 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
Flat in Southold
1BR Apartment - Beach Access - Wineries, Vineyards
1 bedroom, 1 queen bed, 1 bathroom
5–10 Jul
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