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Search results; Over 1,000 homes in Southold

Guest favourite
Home in East Marion
Waterfront Bungalow w/Private Beach on Peconic Bay
3 bedrooms, 4 beds, 1.5 bathrooms
1–8 Aug
4.88 out of 5 average rating, 42 reviews
Superhost
Home in Clinton
The Blue Mermaid
3 bedrooms, 3 beds, 2.5 bathrooms
24–29 Jul
Guest favourite
Home in Shelter Island
New vacation house on the island with the pool
3 bedrooms, 5 beds, 3 bathrooms
16–21 Jul
5.0 out of 5 average rating, 8 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
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
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
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, 253 reviews
Top guest favourite
Rooms in Greenport
Chestnut View Room own private bathroom
2 bedrooms, 3 queen beds, No bathroom
23–28 Aug
5.0 out of 5 average rating, 92 reviews
Home in Shelter Island Heights
Creekside House Shelter Island
4 bedrooms, 5 beds, 3.5 bathrooms
16–23 Jul
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
Guest favourite
Home in Montauk
Dockside 2BR - Marina - Dining - Charter Access Un
2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
4.96 out of 5 average rating, 27 reviews
Guest favourite
Home in Greenport
Bayview house with salt water pool & private chef
3 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
4.9 out of 5 average rating, 10 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, 76 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 East Marion
Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV
3 bedrooms, 3 beds, 3.5 bathrooms
17–24 Jul
5.0 out of 5 average rating, 26 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 East Hampton
Idyllic Designer Sunny Cottage StepsToBeach 1.2 ac
3 bedrooms, 3 beds, 2 bathrooms
17–22 Jul
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Home in Old Saybrook
The Saybrook Point Bungalow, Stroll to Downtown
2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
4.95 out of 5 average rating, 19 reviews