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Search results; Over 1,000 homes in Southold

Top guest favourite
Guest suite in Southold
Comfortable Suite, a walk to the beach
1 bedroom, 1 bed, 1 private bathroom
13–18 Sept
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4.94 out of 5 average rating, 158 reviews
Home in Greenport
Brand New Build! Greenport Gem w/ Yard & Patio
3 bedrooms, 3 beds, 3.5 bathrooms
12–17 Sept
5.0 out of 5 average rating, 3 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, 7 reviews
Guest favourite
Home in East Hampton
4 BD w/ Heated Pool in E Hampton, Fully Furnished
4 bedrooms, 4 beds, 3 bathrooms
12–18 Oct
4.89 out of 5 average rating, 133 reviews
Top guest favourite
Flat in Montauk
Lovely large quiet estate on a nature preserve.
3 bedrooms, 2 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 64 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, 10 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
Top guest favourite
Cottage in Guilford
"Red House on the Knoll" at Indian Cove
3 bedrooms, 5 beds, 2.5 bathrooms
21–26 Sept
4.99 out of 5 average rating, 178 reviews
Home in East Hampton
Simple, Happy Place in East Hampton
2 bedrooms, 2 beds, 1 bathroom
14–19 Oct
5.0 out of 5 average rating, 4 reviews
Home in Cutchogue
Steps to Beach, Vineyards, Farm Stands & Village
3 bedrooms, 3 beds, 2 bathrooms
11–16 Sept
New place to stay
Top guest favourite
Cottage in Sag Harbor
Hamptons Waterfront Getaway – Stylish & Serene
2 bedrooms, 2 queen beds, 2 bathrooms
25–30 Oct
5.0 out of 5 average rating, 18 reviews
Guest favourite
Home in East Marion
Charming North Fork escape by the beach
3 bedrooms, 4 beds, 2 bathrooms
11–18 Sept
5.0 out of 5 average rating, 13 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
Top guest favourite
Home in Old Lyme
Casa Swan
3 bedrooms, 4 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 33 reviews
Top guest favourite
Home in Shelter Island
Beautiful beach home with pool & water views!
5 bedrooms, 9 beds, 3.5 bathrooms
4–9 Oct
4.95 out of 5 average rating, 79 reviews
Guest favourite
Cottage in Clinton
Cozy cottage near Clinton Marina on CT Shoreline
3 bedrooms, 5 beds, 1 bathroom
20–25 Sept
4.95 out of 5 average rating, 93 reviews
Top guest favourite
Flat in Greenport
Upscale Newly Constructed Apartment
3 bedrooms, 6 beds, 2 bathrooms
29 Sept – 4 Oct
4.96 out of 5 average rating, 179 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
Cottage in Shelter Island
3 Bedroom Cottage Gem
3 bedrooms, 4 beds, 2.5 bathrooms
26 Sept – 1 Oct
4.97 out of 5 average rating, 129 reviews