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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
18–23 Sept
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4.89 out of 5 average rating, 197 reviews
Guest favourite
Home in Greenport
Bayview house with salt water pool & private chef
4.9 out of 5 average rating, 10 reviews, 3 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
Top guest favourite
Home in Branford
Adorable Beach House on LI Sound
4.98 out of 5 average rating, 98 reviews, 1 bedroom, 2 beds, 1.5 bathrooms
16–21 Aug
Top guest favourite
Home in East Marion
Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV
5.0 out of 5 average rating, 26 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
12–19 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
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
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
Home in Southold
Beach Front House
5.0 out of 5 average rating, 7 reviews, 4 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
Top guest favourite
Home in East Hampton
Idyllic Designer Sunny Cottage StepsToBeach 1.2 ac
5.0 out of 5 average rating, 18 reviews, 3 bedrooms, 3 beds, 2 bathrooms
12–17 Jul
Guest favourite
Flat in Mattituck
Mattituck 2BR: Open Layout, Deck, BBQ, Near Vines
5.0 out of 5 average rating, 6 reviews, 2 bedrooms, 2 beds, 1 bathroom
12–17 Jul
Guest favourite
Home in Southold
Family and Dog Friendly Private Beach
5.0 out of 5 average rating, 5 reviews, 3 bedrooms, 3 beds, 2 bathrooms
25–30 Jul
Top guest favourite
Home in Old Saybrook
Waterfront Oasis 4Bdr/2b
5.0 out of 5 average rating, 16 reviews, 4 bedrooms, 4 beds, 2 bathrooms
11–16 Oct
Top guest favourite
Rooms in Greenport
Chestnut View Room own private bathroom
5.0 out of 5 average rating, 91 reviews, 2 bedrooms, 3 queen beds, No bathroom
9–14 Aug
Home in Cutchogue
Soundwood Retreat. Get away from the noise.
4 bedrooms, 5 beds, 3 bathrooms
31 May – 5 Jun
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
2–7 Aug
Top guest favourite
Home in Shelter Island
Surf Scoter Cottage Shelter Island
4.91 out of 5 average rating, 93 reviews, 4 bedrooms, 4 beds, 2 bathrooms
23–28 Jul
Home in East Hampton
5 bedroom waterfront on Gardiner's Bay
5.0 out of 5 average rating, 3 reviews, 5 bedrooms, 10 beds, 2 bathrooms
28 Aug – 2 Sept
Top guest favourite
Home in Southold
Best of the North Fork with Heated Pool and Dock
4.97 out of 5 average rating, 33 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
12–17 Sept
Home in Mattituck
3 bed 2 bath sleeps 5 on north fork of Long Island
5.0 out of 5 average rating, 3 reviews, 3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept