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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, 12 reviews
Guest favourite
Home in Shelter Island
New vacation house on the island with the pool
5.0 out of 5 average rating, 8 reviews, 3 bedrooms, 5 beds, 3 bathrooms
6–11 Jul
Superhost
Home in Sag Harbor
Sag Harbor retreat with pool
New place to stay, 3 bedrooms, 4 beds, 1.5 bathrooms
6–11 Jul
Home in Shelter Island
Captain Don’s Paradise
4.92 out of 5 average rating, 13 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
1–6 Aug
Top guest favourite
Flat in Sag Harbor
Sag Harbor / Noyack Pad - private STUDIO apartment
4.95 out of 5 average rating, 182 reviews, 2 beds, 1 bathroom
8–13 Jul
Top guest favourite
Home in Southold
Greenport walk to beach & vineyard! Brand new home
5.0 out of 5 average rating, 76 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
6–11 Jul
Top guest favourite
Home in East Marion
Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV
5.0 out of 5 average rating, 25 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
10–17 Jul
Top guest favourite
Place to stay in Cutchogue
Sunset Suite - walk to vineyards, beaches, & more
4.97 out of 5 average rating, 178 reviews, 1 bedroom, 1 bed, 1 bathroom
4–9 Oct
Top guest favourite
Home in Greenport
The North Star: Greenport Waterview Beach Getaway
4.95 out of 5 average rating, 63 reviews, 3 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
Guest favourite
Home in Southold
Le Petit Cottage, Southold, NY
4.91 out of 5 average rating, 81 reviews, 2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
Top guest favourite
Home in Mattituck
North Fork Getaway Southold Compliant Property
5.0 out of 5 average rating, 14 reviews, 3 bedrooms, 4 beds, 3 bathrooms
8–13 Jul
Guest favourite
Home in Greenport
Blue Bay Dream (Outdoor Jacuzzi, Cabana + Office)
4.92 out of 5 average rating, 506 reviews, 2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
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
6–12 Jul
Top guest favourite
Guest house in Shelter Island
Bayfront 1BR/2BR detached guesthouse with pool
4.99 out of 5 average rating, 74 reviews, 1 bedroom, 2 beds, 1 bathroom
12–17 Sept
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
Room in Southampton
Private suite at Pine Springs, Southampton, NY
5.0 out of 5 average rating, 19 reviews, 2 beds, 1 bathroom
23–28 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
Top guest favourite
Loft in Greenport
Beautiful 2 Bedroom, 2 Bath Greenport Village Loft
4.97 out of 5 average rating, 35 reviews, 2 bedrooms, 3 beds, 2 bathrooms
12–17 Jul
Guest favourite
Home in Orient
Orient Point Family Waterfront Home
4.96 out of 5 average rating, 23 reviews, 5 bedrooms, 9 beds, 3.5 bathrooms
8–13 Jul