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Search results; Over 1,000 homes in Southold

Top guest favourite
Guest suite in Southold
Comfortable Suite, a walk to the beach
1 bedroom, 1 bed, 1 private bathroom
26–31 Jul
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4.94 out of 5 average rating, 150 reviews
Superhost
Home in Clinton
The Blue Mermaid
3 bedrooms, 3 beds, 2.5 bathrooms
24–29 Jul
Home in Old Lyme
Stoneacre at Point O'Woods
2 bedrooms, 2 queen beds, 2 bathrooms
9–14 Aug
Guest favourite
Home in Shelter Island
New vacation house on the island with the pool
3 bedrooms, 5 beds, 3 bathrooms
17–22 Jul
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Cottage in Old Lyme
The Solo Shore Cottage | Walk to Beach + Sun Porch
2 bedrooms, 4 beds, 1 bathroom
2–7 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Flat in Mattituck
Mattituck 2BR: Open Layout, Deck, BBQ, Near Vines
2 bedrooms, 2 queen beds, 1 bathroom
26–31 Jul
5.0 out of 5 average rating, 7 reviews
Home in Laurel
North Fork Luxury Retreat with Exceptional Comfort
5 bedrooms, 5 beds, 3 bathrooms
3–8 Aug
New place to stay
Guest favourite
Home in Old Saybrook
Red Bird Waterfront Home. Dock available extra!
3 bedrooms, 3 beds, 2 bathrooms
26–31 Jul
4.94 out of 5 average rating, 35 reviews
Guest favourite
Home in Greenport
Bayview house with salt water pool & private chef
3 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
4.82 out of 5 average rating, 11 reviews
Home in Sag Harbor
Sun-Filled, Custom-Designed 5-bedroom Sag Harbor
5 bedrooms, 7 beds, 3 bathrooms
20–25 Jul
New place to stay
Top guest favourite
Home in Southold
Beach Front House
4 bedrooms, 4 beds, 2 bathrooms
21–26 Jul
5.0 out of 5 average rating, 7 reviews
Home in East Hampton
Tranquil Springs Cottage
2 bedrooms, 2 queen beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Sag Harbor
Sag Harbor Chic Mid-Century Retreat
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.99 out of 5 average rating, 77 reviews
Top guest favourite
Home in East Marion
Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV
3 bedrooms, 3 beds, 3.5 bathrooms
18–25 Jul
5.0 out of 5 average rating, 26 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, 40 reviews
Home in Sag Harbor
Charming house in Sag Harbor.
3 bedrooms, 3 beds, 2 bathrooms
14–19 Sept
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Cottage in Southampton
Towd Point Beach Cottage w heated pool
3 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
4.98 out of 5 average rating, 48 reviews
Top guest favourite
Home in Southold
Luxury by the Sea!!
3 bedrooms, 4 beds, 2.5 bathrooms
9–14 Aug
4.94 out of 5 average rating, 54 reviews
Home in Sag Harbor
Sag Harbor Cottage Perfection
2 bedrooms, 2 queen beds, 1 bathroom
19–24 Jul
New place to stay