filters

Search results; Over 1,000 homes in Southold

Guest favourite
Cottage in Southold
Cozy Cottage on the Great Pond near beach.
2 bedrooms, 3 beds, 1.5 private bathrooms
27 Jul – 1 Aug
,
4.89 out of 5 average rating, 197 reviews
Top guest favourite
Home in East Marion
Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV
3 bedrooms, 3 beds, 3.5 bathrooms
11–18 Jul
5.0 out of 5 average rating, 25 reviews
Guest favourite
Home in Southold
Family and Dog Friendly Private Beach
3 bedrooms, 3 queen beds, 2 bathrooms
25–30 Jul
5.0 out of 5 average rating, 5 reviews
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!
5 bedrooms, 5 beds, 3 bathrooms
4–9 Oct
4.97 out of 5 average rating, 29 reviews
Guest favourite
Home in East Marion
Charming North Fork escape by the beach
3 bedrooms, 4 beds, 2 bathrooms
8–15 Sept
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Cottage in Shelter Island
Shelter Island Cottage
5 bedrooms, 6 beds, 1.5 bathrooms
9–14 Aug
4.95 out of 5 average rating, 38 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, 6 reviews
Guest favourite
Home in Sag Harbor
Sag Harbor Summer House
3 bedrooms, 4 beds, 2 bathrooms
4–9 Sept
5.0 out of 5 average rating, 7 reviews
Home in East Hampton
Charming Home for a Perfect Escape
5 bedrooms, 8 beds, 3 bathrooms
2–7 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Bungalow in East Hampton
Charming Bungalow on the Bay
2 bedrooms, 7 beds, 1.5 bathrooms
8–13 Aug
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Home in East Hampton
Bay Access Cottage + Pilates Gym
2 bedrooms, 4 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 65 reviews
Guest favourite
Holiday home in Orient
Private Vineyard w/Pool, Walk to Beach & Village
3 bedrooms, 4 beds, 3 bathrooms
17–23 Aug
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Home in Sag Harbor
Sag Harbor Chic Mid-Century Retreat
3 bedrooms, 4 beds, 2 bathrooms
9–14 Aug
4.99 out of 5 average rating, 76 reviews
Top guest favourite
Home in Greenport
The North Star: Greenport Waterview Beach Getaway
3 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
4.95 out of 5 average rating, 63 reviews
Top guest favourite
Home in Shelter Island
Surf Scoter Cottage Shelter Island
4 bedrooms, 4 beds, 2 bathrooms
23–28 Jul
4.91 out of 5 average rating, 93 reviews
Top guest favourite
Home in East Hampton
Water view with Exceptional Light
3 bedrooms, 3 beds, 2 bathrooms
1–6 Oct
4.96 out of 5 average rating, 67 reviews
Home in East Hampton
East Hampton Retreat - Steps from Sammy’s Beach
5 bedrooms, 6 beds, 2.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in East Marion
North Fork Coastal living in East Marion
4 bedrooms, 4 beds, 2.5 bathrooms
2–7 Aug
4.88 out of 5 average rating, 99 reviews