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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
2–7 Aug
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4.94 out of 5 average rating, 149 reviews
Top guest favourite
Home in East Marion
Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV
5.0 out of 5 average rating, 25 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
11–18 Jul
Guest favourite
Home in Southold
Family and Dog Friendly Private Beach
5.0 out of 5 average rating, 5 reviews, 3 bedrooms, 3 beds, 2 bathrooms
25–30 Jul
Home in Amagansett
Unit 211: Cottage | Ocean View | Striper
2 bedrooms, 1 bathroom
20–25 Sept
Top guest favourite
Home in East Marion
POOL + Beach Oasis! Winter deals 2+ nights!
4.97 out of 5 average rating, 29 reviews, 5 bedrooms, 5 beds, 3 bathrooms
4–9 Oct
Guest favourite
Home in East Marion
Charming North Fork escape by the beach
5.0 out of 5 average rating, 12 reviews, 3 bedrooms, 4 beds, 2 bathrooms
8–15 Sept
Top guest favourite
Home in East Hampton
Elegant Springs Retreat (New Construction)
5.0 out of 5 average rating, 6 reviews, 4 bedrooms, 3.5 bathrooms
13–18 Sept
Top guest favourite
Cottage in Shelter Island
Shelter Island Cottage
4.95 out of 5 average rating, 38 reviews, 5 bedrooms, 6 beds, 1.5 bathrooms
9–14 Aug
Guest favourite
Home in Sag Harbor
Sag Harbor Summer House
5.0 out of 5 average rating, 7 reviews, 3 bedrooms, 4 beds, 2 bathrooms
4–9 Sept
Home in East Hampton
Charming Home for a Perfect Escape
5.0 out of 5 average rating, 3 reviews, 5 bedrooms, 8 beds, 3 bathrooms
2–7 Aug
Top guest favourite
Home in East Hampton
Bay Access Cottage + Pilates Gym
5.0 out of 5 average rating, 65 reviews, 2 bedrooms, 4 beds, 1 bathroom
20–25 Sept
Top guest favourite
Home in Greenport
The North Star: Greenport Waterview Beach Getaway
4.95 out of 5 average rating, 63 reviews, 3 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
Guest favourite
Holiday home in Orient
Private Vineyard w/Pool, Walk to Beach & Village
5.0 out of 5 average rating, 21 reviews, 3 bedrooms, 4 beds, 3 bathrooms
17–23 Aug
Top guest favourite
Home in Sag Harbor
Sag Harbor Chic Mid-Century Retreat
4.99 out of 5 average rating, 76 reviews, 3 bedrooms, 4 beds, 2 bathrooms
9–14 Aug
Top guest favourite
Bungalow in East Hampton
Charming Bungalow on the Bay
5.0 out of 5 average rating, 24 reviews, 2 bedrooms, 7 beds, 1.5 bathrooms
8–13 Aug
Top guest favourite
Home in Shelter Island
Surf Scoter Cottage Shelter Island
4.91 out of 5 average rating, 93 reviews, 4 bedrooms, 4 beds, 2 bathrooms
23–28 Jul
Top guest favourite
Home in East Hampton
Water view with Exceptional Light
4.96 out of 5 average rating, 67 reviews, 3 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
Guest favourite
Home in Greenport
Bayview house with salt water pool & private chef
4.9 out of 5 average rating, 10 reviews, 3 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
Home in East Hampton
East Hampton Retreat - Steps from Sammy’s Beach
5.0 out of 5 average rating, 4 reviews, 5 bedrooms, 6 beds, 2.5 bathrooms
7–12 Sept