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Search results; Over 1,000 homes in Southold

Home in Greenport
Greenport Beachfront Home | Private Beach & Sunset
4 bedrooms, 7 beds, 2 bathrooms
2–7 Sept
Home in Westbrook
Luxe 5,600-Sq-Ft Estate Waterfront + Pool
5 bedrooms, 8 beds, 5.5 bathrooms
7–12 Sept
Guest favourite
Home in Peconic
Provence on the North Fork
3 bedrooms, 3 beds, 3 bathrooms
30 Aug – 6 Sept
4.94 out of 5 average rating, 35 reviews
Top guest favourite
Home in Old Saybrook
The Saybrook Point Bungalow, Stroll to Downtown
2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
4.96 out of 5 average rating, 24 reviews
Top guest favourite
Cottage in Old Lyme
The Solo Shore Cottage | Walk to Beach + Sun Porch
2 bedrooms, 4 beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 9 reviews
Home in Old Lyme
Make the "BlueBird" your new summer vacation home!
2 bedrooms, 2 beds, 2 bathrooms
14–19 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Flat in Greenport
Greenport Harbor Apartment
3 bedrooms, 4 beds, 2 bathrooms
19–24 Aug
4.96 out of 5 average rating, 99 reviews
Home in Southampton
Luxury Home with Heated Pool
6 bedrooms, 6 beds, 5 bathrooms
30 Aug – 4 Sept
New place to stay
Guest favourite
Loft in Madison
Walk to Coast! Convenient Cottage in Dtwn Madison
2 beds, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in East Hampton
East Hampton Escape | Pool & Private Beach Access
4 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 23 reviews
Top guest favourite
Guest house in Hampton Bays
Tiana Hideaway - Private Hamptons Studio Retreat
1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in East Hampton
Elegant Springs Retreat (New Construction)
4 bedrooms, 3.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in Clinton
Vintage Shoreline Cottage with Sandy Beach
10 bedrooms, 15 beds, 4 bathrooms
7–12 Sept
4.87 out of 5 average rating, 62 reviews
Top guest favourite
Guest house in Shelter Island
Bayfront 1BR/2BR detached guesthouse with pool
1 bedroom, 2 beds, 1 bathroom
7–12 Sept
4.99 out of 5 average rating, 78 reviews
Home in East Hampton
New East Hampton Cottage
4 bedrooms, 5 beds, 3 bathrooms
13–18 Sept
Top guest favourite
Home in Southold
Luxury by the Sea!!
3 bedrooms, 4 beds, 2.5 bathrooms
30 Aug – 4 Sept
4.95 out of 5 average rating, 56 reviews
Top guest favourite
Home in East Marion
Bohemian Old Life Saving Station with Beach & Pool
6 bedrooms, 8 beds, 4 bathrooms
8–15 Sept
4.97 out of 5 average rating, 114 reviews
Top guest favourite
Home in Montauk
Dockside 2BR - Marina - Dining - Charter Access Un
2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
4.97 out of 5 average rating, 33 reviews