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Search results; Over 1,000 homes in Southold

Guest favourite
Home in Southold
Southold waterfront 4 bed, pool open til October
4 bedrooms, 5 beds, 3 private bathrooms
11–16 Sept
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4.91 out of 5 average rating, 87 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
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
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
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 Marion
Charming North Fork escape by the beach
3 bedrooms, 4 beds, 2 bathrooms
9–16 Sept
5.0 out of 5 average rating, 13 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, 68 reviews
Top guest favourite
Flat in Greenport
Upscale Newly Constructed Apartment
3 bedrooms, 6 beds, 2 bathrooms
11–16 Sept
4.96 out of 5 average rating, 179 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, 6 reviews
Superhost
Home in Old Saybrook
Oceanside retreat Sleeps 8 3bds~3bths
3 bedrooms, 4 beds, 3 bathrooms
9–14 Sept
New place to stay
Superhost
Home in Old Saybrook
Beachfront Home with Amazing Views | 5BR Sleeps 11
5 bedrooms, 7 beds, 2 bathrooms
13–18 Sept
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
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, 94 reviews
Guest favourite
Flat in Greenport
Greenport Condo with Stunning Views & Beach Access
2 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.97 out of 5 average rating, 36 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
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
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
Home in Sag Harbor
Sag Harbor home away from home
2 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
4.98 out of 5 average rating, 237 reviews
Top guest favourite
Home in East Marion
POOL + Beach Oasis! Winter deals 2+ nights!
5 bedrooms, 5 beds, 3 bathrooms
4–9 Oct
4.97 out of 5 average rating, 30 reviews