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Search results; Over 1,000 homes in Southold

Guest favourite
Home in Southold
Beach house @ NoFo
3 bedrooms, 5 beds, 2 private bathrooms
31 Aug – 6 Sept
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4.93 out of 5 average rating, 84 reviews
Home in Greenport
Greenport Beachfront Home | Private Beach & Sunset
4 bedrooms, 7 beds, 2 bathrooms
2–7 Aug
Guest favourite
Home in East Marion
North Fork Coastal living in East Marion
4 bedrooms, 4 beds, 2.5 bathrooms
25–30 Aug
4.88 out of 5 average rating, 99 reviews
Superhost
Tent in East Hampton
Safari Tent Glamping,S5-CedarPt, East Hampton, NY
1 bedroom, 1 queen bed, 1 bathroom
23–28 Aug
4.86 out of 5 average rating, 56 reviews
Guest favourite
Home in Shelter Island
Captain Don’s Paradise
3 bedrooms, 4 beds, 1.5 bathrooms
9–14 Aug
4.92 out of 5 average rating, 13 reviews
Top guest favourite
Home in Old Saybrook
The Saybrook Point Bungalow, Stroll to Downtown
2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
4.95 out of 5 average rating, 22 reviews
Guest favourite
Home in Shelter Island
New vacation house on the island with the pool
3 bedrooms, 5 beds, 3 bathrooms
7–12 Aug
5.0 out of 5 average rating, 8 reviews
Home in Shelter Island Heights
Creekside House Shelter Island
4 bedrooms, 5 beds, 3.5 bathrooms
5–12 Aug
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
Top guest favourite
Home in Sag Harbor
Sag Harbor Summer House
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 11 reviews
Home in East Hampton
Eauclaire Street cozy cottage
3 bedrooms, 3 beds, 2 bathrooms
3–8 Aug
New place to stay
Home in Southold
The Shorecrest Beach House
4 bedrooms, 6 beds, 2 bathrooms
19–24 Oct
5.0 out of 5 average rating, 4 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
Guest favourite
Home in East Marion
Charming North Fork escape by the beach
3 bedrooms, 4 beds, 2 bathrooms
8–15 Sept
5.0 out of 5 average rating, 12 reviews
Home in East Hampton
5 bedroom waterfront on Gardiner's Bay
5 bedrooms, 10 beds, 2 bathrooms
29 Aug – 3 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Cottage in East Lyme
Beach Cottage!
2 bedrooms, 2 queen beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 58 reviews
Guest favourite
Home in Mattituck
3 bed 2 bath sleeps 5 on north fork of Long Island
3 bedrooms, 4 beds, 2 bathrooms
14–19 Aug
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in East Hampton
Elegant Springs Retreat (New Construction)
4 bedrooms, 3.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in Peconic
Provence on the North Fork
3 bedrooms, 3 beds, 3 bathrooms
30 Aug – 6 Sept
4.94 out of 5 average rating, 34 reviews