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Search results; Over 1,000 homes in Southold

Guest favourite
Cottage in Southold
Cozy Cottage on the Great Pond near beach.
2 bedrooms, 3 beds, 1.5 private bathrooms
11–16 Oct
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4.89 out of 5 average rating, 198 reviews
Superhost
Home in Old Saybrook
Beachfront Home with Amazing Views | 5BR Sleeps 11
New place to stay, 5 bedrooms, 7 beds, 2 bathrooms
21–26 Aug
Superhost
Home in Montauk
Sea Ranch At Ditch Plains - Welcome To The Beach
4 bedrooms, 5 beds, 2 bathrooms
10–16 Aug
Top guest favourite
Home in Sag Harbor
Sag Harbor Summer House
5.0 out of 5 average rating, 10 reviews, 3 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
Superhost
Villa in Southampton
US Golf Open & Ocean View Retreat, Walk to Event
4.83 out of 5 average rating, 6 reviews, 4 bedrooms, 4 beds, 3.5 bathrooms
5–10 Oct
Guest favourite
Flat in Greenport
Greenport Harbor Apartment
4.96 out of 5 average rating, 97 reviews, 3 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
Superhost
Home in Clinton
The Blue Mermaid
3 bedrooms, 3 beds, 2.5 bathrooms
1–6 Aug
Top guest favourite
Home in Greenport
The North Star: Greenport Waterview Beach Getaway
4.95 out of 5 average rating, 65 reviews, 3 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
Top guest favourite
Holiday home in Hampton Bays
Hamptons house -ultra-private backyard, near beach
5.0 out of 5 average rating, 17 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
20–25 Sept
Home in East Hampton
Eauclaire Street cozy cottage
New place to stay, 3 bedrooms, 3 beds, 2 bathrooms
2–7 Aug
Home in East Hampton
The Springs House
5.0 out of 5 average rating, 4 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
30 Aug – 4 Sept
Top guest favourite
Home in Sag Harbor
Hamptons Retreat | Pool, Hot Tub, Built-in BBQ
5.0 out of 5 average rating, 8 reviews, 4 bedrooms, 5 beds, 3 bathrooms
14–19 Sept
Guest favourite
Home in Madison
Fabulous pool in beach town!
4.95 out of 5 average rating, 22 reviews, 4 bedrooms, 4 beds, 2.5 bathrooms
21–26 Aug
Top guest favourite
Home in Old Saybrook
Desirable Fenwood Beach-walk to beach-dogs allowed
5.0 out of 5 average rating, 14 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
4–9 Sept
Top guest favourite
Home in East Lyme
Walk to the beach at Black Point, Niantic, Ct
4.98 out of 5 average rating, 167 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
2–8 Aug
Top guest favourite
Home in East Lyme
Charming Cottage in Private Oak Grove Beach
4.97 out of 5 average rating, 73 reviews, 3 bedrooms, 6 beds, 1 bathroom
8–13 Nov
Guest favourite
Home in Orient
Orient Point Family Waterfront Home
4.96 out of 5 average rating, 24 reviews, 5 bedrooms, 9 beds, 3.5 bathrooms
30 Aug – 6 Sept
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
7–12 Aug
Guest favourite
Home in Old Saybrook
Summertime in Old Saybrook on the Oyster River
5.0 out of 5 average rating, 8 reviews, 5 bedrooms, 6 beds, 2.5 bathrooms
9–14 Nov