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Search results; Over 1,000 homes in Southold

Top guest favourite
Home in Old Saybrook
Hot Tub & Firepit•Sunsets & Beach Walk | Fireplace
3 bedrooms, 6 beds, 1.5 bathrooms
24–29 Aug
5.0 out of 5 average rating, 99 reviews
Top guest favourite
Home in East Marion
Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV
3 bedrooms, 3 beds, 3.5 bathrooms
10–15 Aug
5.0 out of 5 average rating, 27 reviews
Guest favourite
Flat in Greenport
Greenport Harbor Apartment
3 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
4.96 out of 5 average rating, 97 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
Guest favourite
Home in Madison
Fabulous pool in beach town!
4 bedrooms, 4 beds, 2.5 bathrooms
21–26 Aug
4.95 out of 5 average rating, 22 reviews
Top guest favourite
Home in Greenport
The North Star: Greenport Waterview Beach Getaway
3 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
4.95 out of 5 average rating, 65 reviews
Home in East Hampton
The Springs House
4 bedrooms, 5 beds, 2.5 bathrooms
11–18 Aug
5.0 out of 5 average rating, 4 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 East Lyme
Charming Cottage in Private Oak Grove Beach
3 bedrooms, 6 beds, 1 bathroom
8–13 Nov
4.97 out of 5 average rating, 72 reviews
Guest favourite
Flat in Greenport
Greenport Condo with Stunning Views & Beach Access
2 bedrooms, 4 beds, 2 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Home in Old Saybrook
Best of both worlds!
3 bedrooms, 4 beds, 2 bathrooms
24–29 Aug
4.92 out of 5 average rating, 113 reviews
Guest favourite
Home in Sag Harbor
Hamptons Retreat | Pool, Hot Tub, Built-in BBQ
4 bedrooms, 5 beds, 3 bathrooms
17–22 Aug
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Shelter Island
New vacation house on the island with the pool
3 bedrooms, 5 beds, 3 bathrooms
1–6 Aug
5.0 out of 5 average rating, 8 reviews
Home in East Hampton
Eauclaire Street cozy cottage
3 bedrooms, 3 beds, 2 bathrooms
2–7 Aug
New place to stay
Top guest favourite
Home in Old Saybrook
Desirable Fenwood Beach-walk to beach-dogs allowed
3 bedrooms, 3 beds, 1.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Holiday home in Hampton Bays
Hamptons house -ultra-private backyard, near beach
3 bedrooms, 4 beds, 2.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 17 reviews
Superhost
Home in Clinton
The Blue Mermaid
3 bedrooms, 3 beds, 2.5 bathrooms
1–6 Aug
Top guest favourite
Home in Shelter Island
Surf Scoter Cottage Shelter Island
4 bedrooms, 4 beds, 2 bathrooms
14–19 Aug
4.91 out of 5 average rating, 94 reviews