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Search results; Over 1,000 homes in Southold

Top guest favourite
Home in Southold
Luxury by the Sea!!
3 bedrooms, 4 beds, 2.5 private bathrooms
30 Aug – 4 Sept
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4.94 out of 5 average rating, 53 reviews
Home in East Hampton
5 bedroom waterfront on Gardiner's Bay
5 bedrooms, 10 beds, 2 bathrooms
12–17 Jul
Top guest favourite
Home in Greenport
The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub
3 bedrooms, 3 beds, 2 bathrooms
10–15 Aug
4.96 out of 5 average rating, 51 reviews
Top guest favourite
Home in Southold
Beach Front House
4 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Sag Harbor
9 Acre Luxury Compound in Sag Harbor NY
7 bedrooms, 10 beds, 8.5 bathrooms
11–16 Oct
4.99 out of 5 average rating, 144 reviews
Home in Orient
Brand new 4 bedrm 4.5 bath home with pool & beach
4 bedrooms, 5 beds, 4.5 bathrooms
7–12 Jul
Top guest favourite
Home in East Marion
Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV
3 bedrooms, 3 beds, 3.5 bathrooms
10–17 Jul
5.0 out of 5 average rating, 25 reviews
Top guest favourite
Home in East Lyme
Walk to the beach at Black Point, Niantic, Ct
3 bedrooms, 4 beds, 2.5 bathrooms
18–24 Sept
4.98 out of 5 average rating, 166 reviews
Top guest favourite
Home in Clinton
The Connecticut Cottage | Historic Modern Charm
2 bedrooms, 2 beds, 2 bathrooms
14–19 Aug
5.0 out of 5 average rating, 16 reviews
Home in East Hampton
Charming Home for a Perfect Escape
5 bedrooms, 8 beds, 3 bathrooms
27 Jul – 1 Aug
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Montauk
Sea Ranch At Ditch Plains - Welcome To The Beach
4 bedrooms, 5 beds, 2 bathrooms
6–11 Dec
Top guest favourite
Room in Sag Harbor
Sag Harbor Home, Perfect for the Solo Traveler
2 beds, 1 bathroom
8–13 Aug
4.96 out of 5 average rating, 248 reviews
Top guest favourite
Home in Westbrook
Home Away From Home
3 bedrooms, 6 beds, 2 bathrooms
20–25 Aug
4.99 out of 5 average rating, 83 reviews
Top guest favourite
Cottage in Shelter Island
Shelter Island Cottage
5 bedrooms, 6 beds, 1.5 bathrooms
9–14 Aug
4.95 out of 5 average rating, 37 reviews
Top guest favourite
Cottage in Old Saybrook
The Cottage
1 bedroom, 2 beds, 1 bathroom
25–30 Aug
4.74 out of 5 average rating, 250 reviews
Top guest favourite
Place to stay in Cutchogue
Sunset Suite - walk to vineyards, beaches, & more
1 bedroom, 1 king bed, 1 bathroom
4–9 Oct
4.97 out of 5 average rating, 177 reviews
Superhost
Home in Sag Harbor
Sag Harbor retreat with pool
3 bedrooms, 4 beds, 1.5 bathrooms
6–11 Jul
New place to stay
Top guest favourite
Cottage in Southampton
10 mins from US OPEN Cottage w heated pool
3 bedrooms, 4 beds, 2 bathrooms
5–10 Jul
4.98 out of 5 average rating, 47 reviews
Top guest favourite
Home in Branford
Adorable Beach House on LI Sound
1 bedroom, 2 beds, 1.5 bathrooms
27 Sept – 2 Oct
4.98 out of 5 average rating, 97 reviews