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Search results; Over 1,000 homes in Southold

Guest favourite
Home in Southold
Shelter Bay Cove Waterfront Escape
3 bedrooms, 3 beds, 2 private bathrooms
8–13 Sept
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4.97 out of 5 average rating, 31 reviews
Guest favourite
Home in Shelter Island
Shelter Island House: Peaceful Retreat
3 bedrooms, 3 beds, 2 bathrooms
6–11 Aug
5.0 out of 5 average rating, 28 reviews
Superhost
Home in Clinton
The Blue Mermaid
3 bedrooms, 3 beds, 2.5 bathrooms
24–29 Jul
Home in Southold
Sunset Cottage
3 bedrooms, 4 beds, 2.5 bathrooms
21–28 Jul
5.0 out of 5 average rating, 5 reviews
Home in Laurel
North Fork Luxury Retreat with Exceptional Comfort
5 bedrooms, 5 beds, 3 bathrooms
3–8 Aug
New place to stay
Top guest favourite
Home in Branford
Adorable Beach House on LI Sound
1 bedroom, 2 beds, 1.5 bathrooms
27 Sept – 2 Oct
4.98 out of 5 average rating, 99 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
Home in Shelter Island Heights
Creekside House Shelter Island
4 bedrooms, 5 beds, 3.5 bathrooms
19–26 Jul
Top guest favourite
Guest house in Shelter Island
Bayfront 1BR/2BR detached guesthouse with pool
1 bedroom, 2 beds, 1 bathroom
8–15 Aug
4.99 out of 5 average rating, 74 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
Guest favourite
Home in Shelter Island
New vacation house on the island with the pool
3 bedrooms, 5 beds, 3 bathrooms
19–24 Jul
5.0 out of 5 average rating, 8 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 Amagansett
Unit 211: Cottage | Ocean View | Striper
2 bedrooms, 1 bathroom
20–25 Sept
Guest favourite
Home in Old Lyme
Casa Swan
3 bedrooms, 4 beds, 1 bathroom
8–13 Aug
5.0 out of 5 average rating, 28 reviews
Home in East Hampton
5 bedroom waterfront on Gardiner's Bay
5 bedrooms, 10 beds, 2 bathrooms
29 Aug – 3 Sept
5.0 out of 5 average rating, 3 reviews
Top 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, 28 reviews
Top guest favourite
Home in East Hampton
Hamptons Beach House
4 bedrooms, 5 beds, 3 bathrooms
22–27 Sept
5.0 out of 5 average rating, 17 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
Guest favourite
Home in Orient
Newly renovated cottage steps to Jitney and shops
2 bedrooms, 3 beds, 1 bathroom
6–11 Aug
5.0 out of 5 average rating, 8 reviews