Woodstock: Vacation Rental By Owner

This lovely spot is just over a mile from the Woodstock Town Green, situated on a small road, nestled into a hillside, where you can watch the leaves change... ...more

This property offers the choice of a fabulous 4 bedroom house that sleeps up to 12, plus for larger groups an optional private, one bedroom guest house down the... ...more

Charming studio cottage in the woods, walking distance to the center of Woodstock. Light-filled cottage is privately set up a tree-lined drive with a stone... ...more

Spacious, modern ranch-style house on 1.9 acres, atop a hill, with plenty of natural sunlight. Designed and decorated for a relaxing time in Woodstock, the home... ...more

Brook Cottage is ideally located on a shared and secluded property at the end of a private lane, yet it’s just a few blocks from the center of Woodstock and the... ...more

The Carriage House is a unique living space that was masterfully designed by the owner-architect to blend modern living with rustic/industrial features of the... ...more

Brookside Retreat is ideally located on a quiet side street overlooking Tannery Brook, a year-round stream that flows through the village of Woodstock, and right... ...more

Relax in your private Woodstock cottage perched on the banks of a meandering mountain stream that flows through a shared mountainside estate on the south side of... ...more

Treat yourself to a romantic getaway or personal retreat in your own private hideaway overlooking the spectacular Tannery Brook waterfall in the quaint and artsy... ...more

Treat yourself to a relaxing, rejuvenating and inspiring retreat in your own private historic studio cottage in the heart of Stonecrop, the estate owned by Anita... ...more

Experience the essence of Woodstock in this former home to Anita M. Smith — artist, historian and “Herb Lady of the Catskills.” Enjoy the fragrance and serenity... ...more

Streamside House is a newly renovated and tastefully furnished 4+ bedroom, 2 full bath + 2 half bath house within easy walking distance to town—about the... ...more

Enjoy the convenience of living one block from the Woodstock village green without sacrificing the peace and beauty of nature! Walk to galleries, boutiques,... ...more

The Teahouse Cottage is on an estate that was the home of Woodstock artist Judson Smith, who used it for one of his studios in the 1940's and 1950's. Later, his... ...more

--------Authentic 18 foot Sioux Tipi, handmade and painted by the artists at Nomadics Tipi Makers. The tipi overlooks a waterfall on the Sawkill Creek that runs... ...more

This spectacular Woodstock estate home is ideal for family or group vacations or retreats. PLEASE NOTE that out of consideration for our neighbors we are no... ...more

This is a charming 'Camping Cabin' in the woods on more than 20 acres of woodlands overlooking a 1 1/2 acre lake. [Some would call it a pond, but it is 10 feet... ...more

Welcome to 'Casa Reál,' an exquisite 4-bedroom, 4-bathroom Spanish-style vacation rental house in Woodstock, New York, with accommodations for 8. This wonderful... ...more

Book your next New York getaway at this lovely 2-bed, 2-bath vacation rental house in Woodstock! This 1,800-square-foot home sleeps 6 and is suitable for events... ...more

Overlooking the Woodstock village center, this antique hotel has 148 years of history and charm. From the front steps you will feel the same energy that travelers... ...more