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Search results; Over 1,000 homes in Southold

Guest favourite
Flat in Southold
Bright, Southold Studio Apt near beach & town
Studio, 2 beds, 1 private bathroom
12–17 Jul
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4.94 out of 5 average rating, 144 reviews
Top guest favourite
Home in Greenport
The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub
4.96 out of 5 average rating, 52 reviews, 3 bedrooms, 3 beds, 2 bathrooms
10–15 Aug
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 Clinton
The Connecticut Cottage | Historic Modern Charm
5.0 out of 5 average rating, 16 reviews, 2 bedrooms, 2 beds, 2 bathrooms
14–19 Aug
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 Southold
Beach Front House
5.0 out of 5 average rating, 7 reviews, 4 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
Home in East Hampton
Charming Home for a Perfect Escape
5.0 out of 5 average rating, 3 reviews, 5 bedrooms, 8 beds, 3 bathrooms
27 Jul – 1 Aug
Top guest favourite
Place to stay in Cutchogue
Sunset Suite - walk to vineyards, beaches, & more
4.97 out of 5 average rating, 177 reviews, 1 bedroom, 1 bed, 1 bathroom
4–9 Oct
Top guest favourite
Home in East Lyme
Walk to the beach at Black Point, Niantic, Ct
4.98 out of 5 average rating, 166 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
18–24 Sept
Top guest favourite
Home in East Marion
Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV
5.0 out of 5 average rating, 25 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
10–17 Jul
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
4.96 out of 5 average rating, 248 reviews, 2 beds, 1 bathroom
8–13 Aug
Top guest favourite
Cottage in Southampton
10 mins from US OPEN Cottage w heated pool
4.98 out of 5 average rating, 47 reviews, 3 bedrooms, 4 beds, 2 bathrooms
5–10 Jul
Top guest favourite
Cottage in Shelter Island
Shelter Island Cottage
4.95 out of 5 average rating, 37 reviews, 5 bedrooms, 6 beds, 1.5 bathrooms
9–14 Aug
Guest favourite
Home in Southold
Charming Ranch in North Fork
5.0 out of 5 average rating, 28 reviews, 3 bedrooms, 5 beds, 1 bathroom
15–20 Aug
Guest favourite
Flat in Mattituck
Mattituck 2BR: Open Layout, Deck, BBQ, Near Vines
5.0 out of 5 average rating, 5 reviews, 2 bedrooms, 2 beds, 1 bathroom
5–10 Jul
Guest favourite
Home in East Marion
Charming North Fork escape by the beach
5.0 out of 5 average rating, 12 reviews, 3 bedrooms, 4 beds, 2 bathrooms
8–15 Sept
Top guest favourite
Cottage in East Lyme
Beach Cottage!
5.0 out of 5 average rating, 54 reviews, 2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
Top guest favourite
Home in Branford
Adorable Beach House on LI Sound
4.98 out of 5 average rating, 97 reviews, 1 bedroom, 2 beds, 1.5 bathrooms
27 Sept – 2 Oct