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Search results; Over 1,000 homes in Southold

Guest favourite
Home in Southold
Luxury Southold waterfront home, heated pool & spa
4 bedrooms, 4 beds, 4 private bathrooms
29 Aug – 5 Sept
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5.0 out of 5 average rating, 12 reviews
Home in East Hampton
5 bedroom waterfront on Gardiner's Bay
5 bedrooms, 10 beds
29 Aug – 3 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Flat in Mattituck
Mattituck 2BR: Open Layout, Deck, BBQ, Near Vines
2 bedrooms, 2 queen beds
9–14 Aug
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Branford
Adorable Beach House on LI Sound
1 bedroom, 2 beds
27 Sept – 2 Oct
4.98 out of 5 average rating, 104 reviews
Top guest favourite
Home in East Hampton
Hamptons Beach House
4 bedrooms, 5 beds
22–27 Sept
5.0 out of 5 average rating, 17 reviews
Superhost
Home in Clinton
The Blue Mermaid
3 bedrooms, 3 beds
3–8 Aug
Guest favourite
Home in Shelter Island
New vacation house on the island with the pool
3 bedrooms, 5 beds
7–12 Aug
5.0 out of 5 average rating, 8 reviews
Home in East Hampton
Eauclaire Street cozy cottage
3 bedrooms, 3 beds
2–7 Aug
New place to stay
Superhost
Villa in Southampton
US Golf Open & Ocean View Retreat, Walk to Event
4 bedrooms, 4 beds
15–20 Oct
4.83 out of 5 average rating, 6 reviews
Top guest favourite
Guest suite in East Hampton
Hamptons Dream Suite
1 bedroom, 3 beds
2–7 Aug
4.98 out of 5 average rating, 160 reviews
Superhost
Home in Montauk
Sea Ranch At Ditch Plains - Welcome To The Beach
4 bedrooms, 5 beds
31 Aug – 6 Sept
Top guest favourite
Home in Greenport
The North Star: Greenport Waterview Beach Getaway
3 bedrooms, 4 beds
28 Sept – 3 Oct
4.95 out of 5 average rating, 65 reviews
Top guest favourite
Home in Sag Harbor
Sag Harbor Summer House
3 bedrooms, 4 beds
7–12 Sept
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Holiday home in Hampton Bays
Hamptons house -ultra-private backyard, near beach
3 bedrooms, 4 beds
20–25 Sept
5.0 out of 5 average rating, 17 reviews
Home in East Hampton
The Springs House
4 bedrooms, 5 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Cottage in Shelter Island
Shelter Island Cottage
5 bedrooms, 6 beds
6–11 Sept
4.95 out of 5 average rating, 41 reviews
Guest favourite
Home in Madison
Fabulous pool in beach town!
4 bedrooms, 4 beds
21–26 Aug
4.95 out of 5 average rating, 22 reviews
Superhost
Home in Sag Harbor
Sag Harbor New Construction
7 bedrooms, 8 beds
7–12 Aug
New place to stay
Guest favourite
Home in Peconic
Provence on the North Fork
3 bedrooms, 3 beds
30 Aug – 6 Sept
4.94 out of 5 average rating, 34 reviews