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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, 196 reviews
Guest favourite
Home in Shelter Island
New vacation house on the island with the pool
3 bedrooms, 5 beds, 3 bathrooms
6–11 Jul
5.0 out of 5 average rating, 8 reviews
Superhost
Home in Sag Harbor
Sag Harbor retreat with pool
3 bedrooms, 4 beds, 1.5 bathrooms
6–11 Jul
New place to stay
Home in Shelter Island
Captain Don’s Paradise
3 bedrooms, 4 beds, 1.5 bathrooms
1–6 Aug
4.92 out of 5 average rating, 13 reviews
Top guest favourite
Flat in Sag Harbor
Sag Harbor / Noyack Pad - private STUDIO apartment
2 beds, 1 bathroom
8–13 Jul
4.95 out of 5 average rating, 182 reviews
Top guest favourite
Place to stay in Cutchogue
Sunset Suite - walk to vineyards, beaches, & more
1 bedroom, 1 king bed, 1 bathroom
4–9 Oct
4.97 out of 5 average rating, 178 reviews
Top guest favourite
Home in East Marion
Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV
3 bedrooms, 3 beds, 3.5 bathrooms
10–17 Jul
5.0 out of 5 average rating, 25 reviews
Top guest favourite
Home in Southold
Greenport walk to beach & vineyard! Brand new home
3 bedrooms, 4 beds, 2.5 bathrooms
6–11 Jul
5.0 out of 5 average rating, 76 reviews
Top guest favourite
Home in Greenport
The North Star: Greenport Waterview Beach Getaway
3 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
4.95 out of 5 average rating, 63 reviews
Top guest favourite
Home in Southold
Private Waterfront Access + Hot Tub + Scenic Yard
3 bedrooms, 5 beds, 2.5 bathrooms
6–12 Jul
5.0 out of 5 average rating, 45 reviews
Guest favourite
Home in Southold
Le Petit Cottage, Southold, NY
2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
4.91 out of 5 average rating, 81 reviews
Guest favourite
Home in Greenport
Blue Bay Dream (Outdoor Jacuzzi, Cabana + Office)
2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
4.92 out of 5 average rating, 506 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
Top guest favourite
Guest house in Shelter Island
Bayfront 1BR/2BR detached guesthouse with pool
1 bedroom, 2 beds, 1 bathroom
12–17 Sept
4.99 out of 5 average rating, 74 reviews
Top guest favourite
Home in Shelter Island
Surf Scoter Cottage Shelter Island
4 bedrooms, 4 beds, 2 bathrooms
23–28 Jul
4.91 out of 5 average rating, 92 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, 53 reviews
Top guest favourite
Room in Southampton
Private suite at Pine Springs, Southampton, NY
2 beds, 1 bathroom
23–28 Jul
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Loft in Greenport
Beautiful 2 Bedroom, 2 Bath Greenport Village Loft
2 bedrooms, 3 beds, 2 bathrooms
12–17 Jul
4.97 out of 5 average rating, 35 reviews
Guest favourite
Home in Greenport
Bayview house with salt water pool & private chef
3 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
4.89 out of 5 average rating, 9 reviews