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Search results; Over 1,000 homes in Southold

Home in Southold
The Shorecrest Beach House
4 bedrooms, 6 beds, 2 private bathrooms
19–24 Oct
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5.0 out of 5 average rating, 4 reviews
Top guest favourite
Room in Greenport
Home on Sterling Harbor, Greenport
1 queen bed, 1 bathroom
23–28 Aug
4.96 out of 5 average rating, 223 reviews
Top guest favourite
Guest suite in East Hampton
Hamptons Dream Suite
1 bedroom, 3 beds, 1 bathroom
23–28 Aug
4.98 out of 5 average rating, 160 reviews
Home in Greenport
Greenport Beachfront Home | Private Beach & Sunset
4 bedrooms, 7 beds, 2 bathrooms
2–7 Aug
Top guest favourite
Cottage in Water Mill
Head of Pond House - Waterfront Cottage
1 bedroom, 2 king beds, 1 bathroom
25–30 Oct
4.97 out of 5 average rating, 79 reviews
Top guest favourite
Room in Greenport
Greenport Village Private Room w/separate entrance
1 queen bed, 1 bathroom
23–28 Aug
4.97 out of 5 average rating, 153 reviews
Top guest favourite
Cottage in Old Lyme
The Solo Shore Cottage | Walk to Beach + Sun Porch
2 bedrooms, 4 beds, 1 bathroom
18–23 Aug
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in East Hampton
Tranquil Springs Cottage
2 bedrooms, 2 queen beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in East Hampton
Hamptons Beach House
4 bedrooms, 5 beds, 3 bathrooms
22–27 Sept
5.0 out of 5 average rating, 17 reviews
Superhost
Home in Niantic
Black Point Beach House — Classic Coastal Escape
3 bedrooms, 4 beds, 1 bathroom
8–13 Aug
New place to stay
Top guest favourite
Cottage in Sag Harbor
Luxury Gem At The Heart of Sag Harbor Village
2 bedrooms, 2 beds, 1.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 68 reviews
Top guest favourite
Room in Sag Harbor
Sag Harbor Home, Perfect for the Solo Traveler
2 beds, 1 bathroom
17–22 Aug
4.96 out of 5 average rating, 256 reviews
Top guest favourite
Room in East Hampton
Peaceful Suite w/Pool, Hot tub, Private Entry.
1 queen bed, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 15 reviews
Guest favourite
Cottage in Old Saybrook
Osprey Cozy Cottage | Near Downtown & Beaches
1 bedroom, 1 queen bed, 1 bathroom
4–9 Aug
5.0 out of 5 average rating, 13 reviews
Guest favourite
Guest house in East Hampton
Private Retreat in a Pristine Studio. 3-night min
1 bedroom, 1 queen bed, 1 bathroom
18–23 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Flat in Old Saybrook
Charming Center of it All Location
2 bedrooms, 2 beds, 1 bathroom
23–28 Aug
4.99 out of 5 average rating, 68 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, 512 reviews
Guest favourite
Rooms in Shelter Island
Room in Charming Coastal Cottage
2 bedrooms, 1 bed, 2 bathrooms
13–18 Sept
4.96 out of 5 average rating, 26 reviews
Top guest favourite
Home in East Lyme
Charming Cottage in Private Oak Grove Beach
3 bedrooms, 6 beds, 1 bathroom
8–13 Nov
4.97 out of 5 average rating, 73 reviews