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Search results; Over 1,000 homes in Southold

Superhost
Home in Montauk
Sea Ranch At Ditch Plains - Welcome To The Beach
4 bedrooms, 5 beds, 2 bathrooms
10–16 Aug
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 Sag Harbor
Sag Harbor Summer House
3 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
5.0 out of 5 average rating, 10 reviews
Guest favourite
Flat in Mattituck
Mattituck 2BR: Open Layout, Deck, BBQ, Near Vines
2 bedrooms, 2 queen beds, 1 bathroom
2–7 Aug
5.0 out of 5 average rating, 7 reviews
Superhost
Home in Clinton
The Blue Mermaid
3 bedrooms, 3 beds, 2.5 bathrooms
1–6 Aug
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 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
Superhost
Villa in Southampton
US Golf Open & Ocean View Retreat, Walk to Event
4 bedrooms, 4 beds, 3.5 bathrooms
5–10 Oct
4.83 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
7–12 Aug
5.0 out of 5 average rating, 8 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
Guest favourite
Home in Orient
Orient Point Family Waterfront Home
5 bedrooms, 9 beds, 3.5 bathrooms
30 Aug – 6 Sept
4.96 out of 5 average rating, 24 reviews
Home in East Hampton
The Springs House
4 bedrooms, 5 beds, 2.5 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 4 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
Top guest favourite
Home in Sag Harbor
Hamptons Retreat | Pool, Hot Tub, Built-in BBQ
4 bedrooms, 5 beds, 3 bathrooms
14–19 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Guest suite in East Hampton
Hamptons Dream Suite
1 bedroom, 3 beds, 1 bathroom
2–7 Aug
4.98 out of 5 average rating, 159 reviews
Guest favourite
Flat in Greenport
Greenport Condo with Stunning Views & Beach Access
2 bedrooms, 4 beds, 2 bathrooms
30 Aug – 4 Sept
4.96 out of 5 average rating, 26 reviews
Superhost
Home in Sag Harbor
Sag Harbor Retreat
7 bedrooms, 8 beds, 8 bathrooms
7–12 Aug
New place to stay