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Search results; Over 1,000 homes in Southold

Guest favourite
Cottage in Southold
Bordeaux meets Côte d’Azur—1763 Historic Farmhouse
3 bedrooms, 4 beds, 2 private bathrooms
15–22 Aug
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4.92 out of 5 average rating, 66 reviews
Superhost
Home in Clinton
The Blue Mermaid
3 bedrooms, 3 beds, 2.5 bathrooms
24–29 Jul
Home in Southold
Sunset Cottage
5.0 out of 5 average rating, 5 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
22–29 Jul
Home in Shelter Island Heights
Creekside House Shelter Island
4 bedrooms, 5 beds, 3.5 bathrooms
20–27 Jul
Top guest favourite
Cottage in Shelter Island
Shelter Island Cottage
4.95 out of 5 average rating, 40 reviews, 5 bedrooms, 6 beds, 1.5 bathrooms
6–11 Sept
Superhost
Tent in East Hampton
Safari Tent Glamping,S5-CedarPt, East Hampton, NY
4.86 out of 5 average rating, 56 reviews, 1 bedroom, 3 beds, 1 bathroom
26–31 Jul
Guest favourite
Home in East Marion
North Fork Coastal living in East Marion
4.88 out of 5 average rating, 99 reviews, 4 bedrooms, 4 beds, 2.5 bathrooms
28 Jul – 2 Aug
Top guest favourite
Home in Branford
Adorable Beach House on LI Sound
4.98 out of 5 average rating, 100 reviews, 1 bedroom, 2 beds, 1.5 bathrooms
27 Sept – 2 Oct
Guest favourite
Home in Shelter Island
Shelter Island House: Peaceful Retreat
5.0 out of 5 average rating, 28 reviews, 3 bedrooms, 3 beds, 2 bathrooms
6–11 Aug
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
Home in East Hampton
Charming Home for a Perfect Escape
5.0 out of 5 average rating, 5 reviews, 5 bedrooms, 8 beds, 3 bathrooms
30 Aug – 4 Sept
Guest favourite
Home in Old Lyme
Casa Swan
5.0 out of 5 average rating, 28 reviews, 3 bedrooms, 4 beds, 1 bathroom
8–13 Aug
Guest favourite
Cottage in Old Lyme
The Solo Shore Cottage | Walk to Beach + Sun Porch
5.0 out of 5 average rating, 6 reviews, 2 bedrooms, 4 beds, 1 bathroom
18–23 Aug
Top guest favourite
Guest house in Shelter Island
Bayfront 1BR/2BR detached guesthouse with pool
4.99 out of 5 average rating, 74 reviews, 1 bedroom, 2 beds, 1 bathroom
8–15 Aug
Top guest favourite
Home in Old Saybrook
Best of both worlds!
4.92 out of 5 average rating, 111 reviews, 3 bedrooms, 4 beds, 2 bathrooms
24–29 Aug
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
Home in Sag Harbor
Charming house in Sag Harbor.
5.0 out of 5 average rating, 10 reviews, 3 bedrooms, 3 beds, 2 bathrooms
14–19 Sept
Home in Sag Harbor
1 Acre Sag Harbor Gem
4 bedrooms, 5 beds, 3 bathrooms
23–30 Aug
Top guest favourite
Home in Westbrook
Home Away From Home
4.99 out of 5 average rating, 84 reviews, 3 bedrooms, 6 beds, 2 bathrooms
20–25 Aug