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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
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, 12 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 Southold
Waterfront North Fork Retreat • Sunset & Vineyards
4 bedrooms, 5 beds, 3 bathrooms
19–26 Jul
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, 80 reviews
Guest favourite
Home in Shelter Island
New vacation house on the island with the pool
3 bedrooms, 5 beds, 3 bathrooms
5–10 Jul
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Cottage in Southampton
10 mins from US OPEN Cottage w heated pool
3 bedrooms, 4 beds, 2 bathrooms
5–10 Jul
4.98 out of 5 average rating, 47 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
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, 177 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
Top guest favourite
Loft in Greenport
Beautiful 2 Bedroom, 2 Bath Greenport Village Loft
2 bedrooms, 3 beds, 2 bathrooms
5–10 Jul
4.97 out of 5 average rating, 35 reviews
Top guest favourite
Home in Greenport
The North Star: Greenport Waterview Beach Getaway
3 bedrooms, 4 beds, 2 bathrooms
4–9 Aug
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
5–11 Jul
5.0 out of 5 average rating, 45 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
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, 18 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, 73 reviews
Guest favourite
Home in Mattituck
Lakehouse Getaway North Fork
3 bedrooms, 5 beds, 2 bathrooms
11–16 Jul
5.0 out of 5 average rating, 44 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
Guest favourite
Room in Cutchogue
Glam Garden Grotto
1 bed, 1 bathroom
3–8 Aug
5.0 out of 5 average rating, 11 reviews