filters

Search results; Over 1,000 homes in Southold

Guest favourite
Home in Southold
Shelter Bay Cove Waterfront Escape
3 bedrooms, 3 beds, 2 private bathrooms
5–10 Sept
,
4.97 out of 5 average rating, 31 reviews
Top guest favourite
Flat in Mattituck
Mattituck 2BR: Open Layout, Deck, BBQ, Near Vines
2 bedrooms, 2 queen beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Cottage in Old Lyme
The Solo Shore Cottage | Walk to Beach + Sun Porch
2 bedrooms, 4 beds, 1 bathroom
18–23 Aug
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Shelter Island
New vacation house on the island with the pool
3 bedrooms, 5 beds, 3 bathrooms
7–12 Aug
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in East Hampton
Hamptons Beach House
4 bedrooms, 5 beds, 3 bathrooms
22–27 Sept
5.0 out of 5 average rating, 17 reviews
Home in Amagansett
Lazy Point Gem w access to Private Beach
3 bedrooms, 3 beds, 1 bathroom
5–10 Aug
New place to stay
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, 66 reviews
Superhost
Home in Montauk
Sea Ranch At Ditch Plains - Welcome To The Beach
4 bedrooms, 5 beds, 2 bathrooms
31 Aug – 6 Sept
Home in Shelter Island Heights
Creekside House Shelter Island
4 bedrooms, 5 beds, 3.5 bathrooms
5–12 Aug
Guest favourite
Home in East Marion
North Fork Coastal living in East Marion
4 bedrooms, 4 beds, 2.5 bathrooms
18–23 Aug
4.88 out of 5 average rating, 99 reviews
Superhost
Tent in East Hampton
Safari Tent Glamping,S5-CedarPt, East Hampton, NY
1 bedroom, 1 queen bed, 1 bathroom
23–28 Aug
4.86 out of 5 average rating, 56 reviews
Home in East Hampton
5 bedroom waterfront on Gardiner's Bay
5 bedrooms, 10 beds, 2 bathrooms
29 Aug – 3 Sept
5.0 out of 5 average rating, 3 reviews
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, 55 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
Guest favourite
Flat in Greenport
Greenport Condo with Stunning Views & Beach Access
2 bedrooms, 4 beds, 2 bathrooms
30 Aug – 4 Sept
4.97 out of 5 average rating, 29 reviews
Top guest favourite
Cottage in Sag Harbor
Charming Cottage in Historic Sag Harbor
1 bedroom, 1 king bed, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 69 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 Mattituck
Lakehouse Getaway North Fork
3 bedrooms, 5 beds, 2 bathrooms
16–21 Aug
5.0 out of 5 average rating, 46 reviews
Guest favourite
Home in Greenport
Aqua Vista
2 bedrooms, 3 beds, 1 bathroom
28 Aug – 2 Sept
4.95 out of 5 average rating, 264 reviews