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Search results; Over 1,000 homes in Southold

Guest favourite
Cottage in Southold
Cozy Cottage on the Great Pond near beach.
2 bedrooms, 3 beds, 1.5 private bathrooms
27 Jul – 1 Aug
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4.9 out of 5 average rating, 196 reviews
Top guest favourite
Home in East Marion
Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV
3 bedrooms, 3 beds
10–17 Jul
5.0 out of 5 average rating, 25 reviews
Home in East Hampton
5 bedroom waterfront on Gardiner's Bay
5 bedrooms, 10 beds
12–17 Jul
Top guest favourite
Home in Old Saybrook
The Saybrook Point Bungalow, Stroll to Downtown
2 bedrooms, 3 beds
16–21 Aug
4.93 out of 5 average rating, 15 reviews
Home in East Hampton
Charming Home for a Perfect Escape
5 bedrooms, 8 beds
27 Jul – 1 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Clinton
The Connecticut Cottage | Historic Modern Charm
2 bedrooms, 2 beds
14–19 Aug
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Home in Southold
Beach Front House
4 bedrooms, 4 beds
19–24 Jul
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in Southold
Family and Dog Friendly Private Beach
3 bedrooms, 3 queen beds
25–30 Jul
5.0 out of 5 average rating, 5 reviews
Superhost
Home in Montauk
Sea Ranch At Ditch Plains - Welcome To The Beach
4 bedrooms, 5 beds
6–11 Dec
Guest favourite
Flat in Mattituck
Mattituck 2BR: Open Layout, Deck, BBQ, Near Vines
2 bedrooms, 2 queen beds
12–17 Jul
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Old Lyme
Casa Swan
3 bedrooms, 4 beds
9–14 Aug
5.0 out of 5 average rating, 28 reviews
Top guest favourite
Home in Old Saybrook
Waterfront Oasis 4Bdr/2b
4 bedrooms, 4 beds
11–16 Oct
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Cottage in Shelter Island
Shelter Island Cottage
5 bedrooms, 6 beds
9–14 Aug
4.95 out of 5 average rating, 37 reviews
Guest favourite
Home in Clinton
Vintage Shoreline Cottage with Sandy Beach
10 bedrooms, 15 beds
9–15 Sept
4.86 out of 5 average rating, 59 reviews
Guest favourite
Home in Southold
Charming Ranch in North Fork
3 bedrooms, 5 beds
15–20 Aug
5.0 out of 5 average rating, 28 reviews
Top guest favourite
Flat in Greenport
Newly Renovated 2-BR Apartment
2 bedrooms, 5 beds
26–31 Jul
4.98 out of 5 average rating, 87 reviews
Top guest favourite
Cottage in East Lyme
Beach Cottage!
2 bedrooms, 2 queen beds
13–18 Sept
5.0 out of 5 average rating, 54 reviews
Top guest favourite
Flat in Greenport
Upscale Newly Constructed Apartment
3 bedrooms, 6 beds
9–14 Sept
4.96 out of 5 average rating, 171 reviews
Top guest favourite
Home in East Hampton
East Hampton Rental w/ Pool, Moments to Amenities
4 bedrooms, 5 beds
1–6 Aug
5.0 out of 5 average rating, 82 reviews