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Search results; Over 1,000 homes in Southold

Home in East Hampton
East Hampton Beach House | Private Beach
4 bedrooms, 5 beds, 3 bathrooms
20–25 Sept
New place to stay
Superhost
Home in Old Lyme
Connecticut Beach Home
Business host
15–20 Sept
New place to stay
Guest favourite
Home in Southampton
Vogue Editors Home, Featured Hamptons Mag, Elle D.
4 bedrooms, 4 beds, 7.5 bathrooms
11–16 Oct
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Amagansett
Ocean views, steps to beach, newly renovated home
5 bedrooms, 7 beds, 3 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 22 reviews
Luxe
Villa in East Hampton
Luxe|Pool|Games|Movie|HotTub|Firepit|MegaChess
3 bedrooms, 3 beds, 3.5 bathrooms
30 Sept – 5 Oct
4.99 out of 5 average rating, 69 reviews
Guest favourite
Home in Greenport
Greenport Beachfront Home | Private Beach & Sunset
4 bedrooms, 7 beds, 2 bathrooms
17–22 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Old Saybrook
Desirable Fenwood Beach-walk to beach-dogs allowed
3 bedrooms, 3 beds, 1.5 bathrooms
12–17 Oct
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Home in East Hampton
Designer East Hampton with Bay Views + Pool
4 bedrooms, 4 beds, 3.5 bathrooms
25–30 Sept
5.0 out of 5 average rating, 31 reviews
Top guest favourite
Home in East Hampton
Elegant Springs Retreat (New Construction)
4 bedrooms, 3.5 bathrooms
21–26 Sept
5.0 out of 5 average rating, 11 reviews
Home in East Hampton
East Hamptons Modern 8 Bedroom New Construction
8 bedrooms, 8 beds, 6 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in East Marion
New! 6BR, 4.5 Bath, Pool, Hot Tub, Walk to Beach
6 bedrooms, 8 beds, 4.5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 26 reviews
Top guest favourite
Home in East Marion
Bohemian Old Life Saving Station with Beach & Pool
6 bedrooms, 8 beds, 4 bathrooms
27 Sept – 2 Oct
4.97 out of 5 average rating, 114 reviews
Top guest favourite
Home in East Hampton
East Hampton Rental w/ Pool, Moments to Amenities
4 bedrooms, 5 beds, 3 bathrooms
11–16 Oct
5.0 out of 5 average rating, 95 reviews
Guest favourite
Home in Sag Harbor
9 Acre Luxury Compound in Sag Harbor NY
7 bedrooms, 10 beds, 8.5 bathrooms
11–16 Oct
4.99 out of 5 average rating, 148 reviews
Top guest favourite
Home in East Marion
Long Island home with pool 1 mile from Greenport
3 bedrooms, 3 beds, 2 bathrooms
13–18 Oct
5.0 out of 5 average rating, 23 reviews
Home in Shelter Island
Waterfront Retreat | Spa Pool, Sauna & Dock
3 bedrooms, 3 beds, 3.5 bathrooms
21–26 Sept
New place to stay
Top guest favourite
Home in Southold
Country Beach Home!
4 bedrooms, 8 beds, 2.5 bathrooms
20–25 Sept
4.96 out of 5 average rating, 23 reviews
Top guest favourite
Home in Shelter Island
Shelter Island 4 BR w Pool & Private Beach Access
4 bedrooms, 7 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 11 reviews