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Search results; Over 1,000 homes in Southold

Guest favourite
Home in Southold
Shelter Bay Cove Waterfront Escape
3 bedrooms, 3 beds, 2 private bathrooms
8–13 Sept
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4.97 out of 5 average rating, 31 reviews
Home in East Hampton
East Hamptons 3BR Private +Den Private Entrance
New place to stay, 3 bedrooms, 2 beds, 2 bathrooms
1–6 Aug
Guest favourite
Flat in Greenport
Greenport Harbor Apartment
4.96 out of 5 average rating, 97 reviews, 3 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
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
1–6 Aug
Top guest favourite
Home in East Hampton
Hamptons Beach House
5.0 out of 5 average rating, 17 reviews, 4 bedrooms, 5 beds, 3 bathrooms
22–27 Sept
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
30 Aug – 6 Sept
Guest favourite
Home in Shelter Island
Captain Don’s Paradise
4.92 out of 5 average rating, 13 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
3–8 Aug
Guest favourite
Home in East Hampton
Private East Hampton Oasis
5.0 out of 5 average rating, 8 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
25–31 Aug
Superhost
Home in Montauk
Sea Ranch At Ditch Plains - Welcome To The Beach
4 bedrooms, 5 beds, 2 bathrooms
6–11 Dec
Superhost
Tent in East Hampton
Safari Tent Glamping,S5-CedarPt, East Hampton, NY
4.86 out of 5 average rating, 56 reviews, 1 bedroom, 3 beds, 1 bathroom
1–6 Aug
Superhost
Cabin in East Hampton
Modern Cabin near the Beach
3 bedrooms, 6 beds, 3 bathrooms
10–15 Aug
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
1–8 Aug
Home in Southold
The Shorecrest Beach House
5.0 out of 5 average rating, 4 reviews, 4 bedrooms, 6 beds, 2 bathrooms
14–19 Oct
Home in East Hampton
Tranquil Springs Cottage
5.0 out of 5 average rating, 4 reviews, 2 bedrooms, 2 beds, 1 bathroom
23–28 Aug
Home in East Hampton
5 bedroom waterfront on Gardiner's Bay
5.0 out of 5 average rating, 3 reviews, 5 bedrooms, 10 beds, 2 bathrooms
29 Aug – 3 Sept
Guest favourite
Home in Madison
Fabulous pool in beach town!
4.95 out of 5 average rating, 22 reviews, 4 bedrooms, 4 beds, 2.5 bathrooms
21–26 Aug
Top guest favourite
Home in Greenport
The North Star: Greenport Waterview Beach Getaway
4.95 out of 5 average rating, 65 reviews, 3 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
Guest favourite
Flat in Greenport
Greenport Condo with Stunning Views & Beach Access
5.0 out of 5 average rating, 23 reviews, 2 bedrooms, 4 beds, 2 bathrooms
30 Aug – 4 Sept
Top guest favourite
Home in East Marion
Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV
5.0 out of 5 average rating, 27 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
10–15 Aug