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Search results; Over 1,000 homes in Southold

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Home in Sag Harbor
Sag Harbor New Construction
7 bedrooms, 9 beds, 8 bathrooms
16–21 Aug
New place to stay
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Home in Montauk
Sea Ranch At Ditch Plains - Welcome To The Beach
4 bedrooms, 5 beds, 2 bathrooms
31 Aug – 6 Sept
Home in Amagansett
Lazy Point Gem w access to Private Beach
3 bedrooms, 3 beds, 1 bathroom
17–22 Aug
New place to stay
Guest favourite
Flat in Mattituck
Mattituck 2BR: Open Layout, Deck, BBQ, Near Vines
2 bedrooms, 2 queen beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 8 reviews
Guest favourite
Cottage in Old Lyme
The Solo Shore Cottage | Walk to Beach + Sun Porch
2 bedrooms, 4 beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in East Marion
North Fork Coastal living in East Marion
4 bedrooms, 4 beds, 2.5 bathrooms
18–23 Aug
4.88 out of 5 average rating, 99 reviews
Top guest favourite
Home in Southold
Luxury by the Sea!!
3 bedrooms, 4 beds, 2.5 bathrooms
30 Aug – 4 Sept
4.95 out of 5 average rating, 55 reviews
Guest favourite
Home in Peconic
Provence on the North Fork
3 bedrooms, 3 beds, 3 bathrooms
30 Aug – 6 Sept
4.94 out of 5 average rating, 34 reviews
Guest favourite
Home in Sag Harbor
9 Acre Luxury Compound in Sag Harbor NY
7 bedrooms, 10 beds, 8.5 bathrooms
11–16 Oct
4.99 out of 5 average rating, 146 reviews
Guest favourite
Home in Shelter Island
Captain Don’s Paradise
3 bedrooms, 4 beds, 1.5 bathrooms
30 Aug – 4 Sept
4.92 out of 5 average rating, 13 reviews
Guest favourite
Rooms in East Hampton
Two Lovely Private Rooms
2 bedrooms, 2 queen beds, 1 bathroom
7–12 Sept
4.95 out of 5 average rating, 22 reviews
Top guest favourite
Home in Old Lyme
Casa Swan
3 bedrooms, 4 beds, 1 bathroom
24–29 Aug
5.0 out of 5 average rating, 32 reviews
Top guest favourite
Home in Old Lyme
Cozy Beach Cottage with short walk to the beach
4 bedrooms, 5 beds, 1.5 bathrooms
23–28 Aug
4.97 out of 5 average rating, 198 reviews
Home in East Hampton
Simple, Happy Place in East Hampton
2 bedrooms, 2 beds, 1 bathroom
31 Aug – 5 Sept
New place to stay
Home in Wainscott
Charming Wainscott Cottage
2 bedrooms, 3 beds, 1.5 bathrooms
31 Aug – 5 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in East Hampton
Elegant Springs Retreat (New Construction)
4 bedrooms, 3.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in East Hampton
Charming Home for a Perfect Escape
5 bedrooms, 8 beds, 3 bathrooms
30 Aug – 4 Sept
4.9 out of 5 average rating, 10 reviews
Guest favourite
Home in Greenport
Bayview house with salt water pool & private chef
3 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
4.88 out of 5 average rating, 16 reviews