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Search results; Over 1,000 homes in Southold

Guest favourite
Guest house in Southold
Southold- Adorable 1 Bedroom Cottage
1 bedroom, 1 bed, 1 private bathroom
4–9 Oct
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4.91 out of 5 average rating, 86 reviews
Home in Greenport
Greenport Beachfront Home | Private Beach & Sunset
4 bedrooms, 7 beds, 2 bathrooms
3–8 Aug
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 Mattituck
Lakehouse Getaway North Fork
3 bedrooms, 5 beds, 2 bathrooms
16–21 Aug
5.0 out of 5 average rating, 46 reviews
Guest favourite
Home in Clinton
Historic Coastal Home • Marsh Views • Pet-Friendly
4 bedrooms, 4 beds, 3.5 bathrooms
9–14 Aug
5.0 out of 5 average rating, 13 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 East Hampton
Hamptons Beach House
4 bedrooms, 5 beds, 3 bathrooms
22–27 Sept
5.0 out of 5 average rating, 17 reviews
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
Home in East Hampton
Eauclaire Street cozy cottage
3 bedrooms, 3 beds, 2 bathrooms
3–8 Aug
New place to stay
Superhost
Home in Montauk
Sea Ranch At Ditch Plains - Welcome To The Beach
4 bedrooms, 5 beds, 2 bathrooms
31 Aug – 6 Sept
Top guest favourite
Home in Laurel
Peaceful Guesthouse
2 bedrooms, 2 beds, 1.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 34 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
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 Old Saybrook
Summertime in Old Saybrook on the Oyster River
5 bedrooms, 6 beds, 2.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 9 reviews
Home in Shelter Island Heights
Creekside House Shelter Island
4 bedrooms, 5 beds, 3.5 bathrooms
5–12 Aug
Guest favourite
Home in East Hampton
Charming Home for a Perfect Escape
5 bedrooms, 8 beds, 3 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Southold
Luxury by the Sea!!
3 bedrooms, 4 beds, 2.5 bathrooms
30 Aug – 4 Sept
4.95 out of 5 average rating, 55 reviews
Flat in East Lyme
Charming cottage above beloved Black Point Market
3 bedrooms, 4 beds, 1 bathroom
17–22 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