filters

Search results; Over 1,000 homes in Southold

Home in Southold
Shelter Bay Cove Waterfront Escape
3 bedrooms, 3 beds, 2 private bathrooms
5–10 Sept
,
4.91 out of 5 average rating, 32 reviews
Top guest favourite
Home in Old Saybrook
Hot Tub & Firepit•Sunsets & Beach Walk | Fireplace
3 bedrooms, 6 beds, 1.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 103 reviews
Top guest favourite
Home in Wainscott
Charming Wainscott Cottage
2 bedrooms, 3 beds, 1.5 bathrooms
21–26 Sept
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Cottage in Shelter Island
3 Bedroom Cottage Gem
3 bedrooms, 4 beds, 2.5 bathrooms
6–11 Sept
4.97 out of 5 average rating, 129 reviews
Guest favourite
Home in Southampton
Vogue Editors Home, Featured Hamptons Mag, Elle D.
4 bedrooms, 4 beds, 7.5 bathrooms
11–16 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Sag Harbor
Relax into Coastal Life at a Sun-Drenched Sag Harbor Home
3 bedrooms, 3 beds, 2 bathrooms
29 Oct – 3 Nov
4.98 out of 5 average rating, 170 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, 93 reviews
Top guest favourite
Home in East Marion
Long Island home with pool 1 mile from Greenport
3 bedrooms, 3 beds, 2 bathrooms
13–18 Oct
5.0 out of 5 average rating, 23 reviews
Home in Westbrook
Cottage on the beach
3 bedrooms, 3 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Old Saybrook
Desirable Fenwood Beach-walk to beach-dogs allowed
3 bedrooms, 3 beds, 1.5 bathrooms
17–22 Sept
5.0 out of 5 average rating, 17 reviews
Home in Greenport
Brand New Build! Greenport Gem w/ Yard & Patio
3 bedrooms, 3 beds, 3.5 bathrooms
12–17 Sept
New place to stay
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
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, 236 reviews
Top guest favourite
Home in Old Saybrook
Year Round Beach House in Old Saybrook, CT.- Pets
4 bedrooms, 7 beds, 2 bathrooms
9–14 Sept
4.97 out of 5 average rating, 146 reviews
Top guest favourite
Home in East Hampton
Beautiful east hampton cottage by the bay
4 bedrooms, 2 queen beds, 2.5 bathrooms
9–14 Sept
5.0 out of 5 average rating, 16 reviews
Superhost
Home in Old Saybrook
Oceanside retreat Sleeps 8 3bds~3bths
3 bedrooms, 4 beds, 3 bathrooms
8–13 Sept
New place to stay
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, 177 reviews
Top guest favourite
Cottage in Sag Harbor
Hamptons Waterfront Getaway – Stylish & Serene
2 bedrooms, 2 queen beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 18 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