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Search results; Over 1,000 homes in Southold

Top guest favourite
Home in East Marion
Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV
5.0 out of 5 average rating, 26 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
13–20 Jul
Home in Amagansett
Unit 211: Cottage | Ocean View | Striper
2 bedrooms, 1 bathroom
20–25 Sept
Guest favourite
Home in East Marion
Charming North Fork escape by the beach
5.0 out of 5 average rating, 12 reviews, 3 bedrooms, 4 beds, 2 bathrooms
8–15 Sept
Top guest favourite
Cottage in Shelter Island
Shelter Island Cottage
4.95 out of 5 average rating, 39 reviews, 5 bedrooms, 6 beds, 1.5 bathrooms
9–14 Aug
Home in East Hampton
Charming Home for a Perfect Escape
5.0 out of 5 average rating, 3 reviews, 5 bedrooms, 8 beds, 3 bathrooms
30 Aug – 4 Sept
Top guest favourite
Home in East Marion
POOL + Beach Oasis! Winter deals 2+ nights!
4.97 out of 5 average rating, 29 reviews, 5 bedrooms, 5 beds, 3 bathrooms
4–9 Oct
Guest favourite
Home in Southold
Family and Dog Friendly Private Beach
5.0 out of 5 average rating, 5 reviews, 3 bedrooms, 3 beds, 2 bathrooms
25–30 Jul
Guest favourite
Home in Old Lyme
Casa Swan
5.0 out of 5 average rating, 28 reviews, 3 bedrooms, 4 beds, 1 bathroom
8–13 Aug
Top guest favourite
Home in Sag Harbor
9 Acre Luxury Compound in Sag Harbor NY
4.99 out of 5 average rating, 144 reviews, 7 bedrooms, 10 beds, 8.5 bathrooms
10–15 Aug
Home in Laurel
North Fork Luxury Retreat with Exceptional Comfort
New place to stay, 5 bedrooms, 5 beds, 3 bathrooms
14–19 Jul
Guest favourite
Home in Sag Harbor
Sag Harbor Haven
4.82 out of 5 average rating, 22 reviews, 6 bedrooms, 8 beds, 4 bathrooms
21–26 Sept
Guest favourite
Home in Greenport
Bayview house with salt water pool & private chef
4.9 out of 5 average rating, 10 reviews, 3 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
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
13–18 Jul
Home in Shelter Island
Private Shelter Island Escape | Huge Yard + Pool
4 bedrooms, 5 beds, 2.5 bathrooms
9–14 Aug
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
Top guest favourite
Home in Sag Harbor
Sag Harbor Chic Mid-Century Retreat
4.99 out of 5 average rating, 76 reviews, 3 bedrooms, 4 beds, 2 bathrooms
9–14 Aug
Home in East Hampton
East Hampton Retreat - Steps from Sammy’s Beach
5.0 out of 5 average rating, 4 reviews, 5 bedrooms, 6 beds, 2.5 bathrooms
7–12 Sept
Top guest favourite
Home in Sag Harbor
Sag Harbor Summer House
5.0 out of 5 average rating, 7 reviews, 3 bedrooms, 4 beds, 2 bathrooms
4–9 Sept