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Search results; Over 1,000 homes in Southold

Top guest favourite
Flat in Mattituck
Mattituck 2BR: Open Layout, Deck, BBQ, Near Vines
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 2 beds, 1 bathroom
26–31 Jul
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
5.0 out of 5 average rating, 8 reviews, 3 bedrooms, 5 beds, 3 bathrooms
16–21 Jul
Guest favourite
Home in Old Saybrook
Red Bird Waterfront Home. Dock available extra!
4.94 out of 5 average rating, 35 reviews, 3 bedrooms, 3 beds, 2 bathrooms
26–31 Jul
Guest favourite
Home in Water Mill
Water Mill Retreat
5.0 out of 5 average rating, 12 reviews, 3 bedrooms, 4 beds, 2 bathrooms
27 Jul – 1 Aug
Home in East Hampton
Tranquil Springs Cottage
5.0 out of 5 average rating, 4 reviews, 2 bedrooms, 2 beds, 1 bathroom
23–28 Aug
Top guest favourite
Cottage in Southampton
Towd Point Beach Cottage w heated pool
4.98 out of 5 average rating, 48 reviews, 3 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
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
27 Sept – 2 Oct
Guest favourite
Home in Montauk
Dockside 2BR - Marina - Dining - Charter Access Un
4.96 out of 5 average rating, 28 reviews, 2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
Top guest favourite
Home in Old Saybrook
The Saybrook Point Bungalow, Stroll to Downtown
4.95 out of 5 average rating, 19 reviews, 2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
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
5.0 out of 5 average rating, 5 reviews, 2 bedrooms, 4 beds, 1 bathroom
2–7 Aug
Guest favourite
Home in Greenport
Bayview house with salt water pool & private chef
4.82 out of 5 average rating, 11 reviews, 3 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
Top guest favourite
Rooms in Greenport
Chestnut View Room own private bathroom
5.0 out of 5 average rating, 92 reviews, 2 bedrooms, 3 queen beds, No bathroom
23–28 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
17–24 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
21–26 Jul
Top guest favourite
Home in East Hampton
Idyllic Designer Sunny Cottage StepsToBeach 1.2 ac
5.0 out of 5 average rating, 19 reviews, 3 bedrooms, 3 beds, 2 bathrooms
17–22 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
29 Aug – 3 Sept