Woodstock: Vacation Rental By Owner

Showing 20 Of 100 Vacation Rentals
  • Property-1 Image 1
    House $423 / Nightly
    • 3 Bed
    • 2 Baths
    • (34) Excellent
    Woodstock, NY

    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

  • Property-2 Image 1
    Chalet $517 / Nightly
    • 5 Bed
    • 4 Baths
    • (40) Wonderful
    Woodstock, NY

    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

  • Property-3 Image 1
    Cottage $179 / Nightly
    • 1 Bed
    • 1 Baths
    • (49)
    Woodstock, NY

    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

  • Property-4 Image 1
    House $304 / Nightly
    • 3 Bed
    • 3 Baths
    • (5) Exceptional
    Woodstock, NY

    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

  • Property-5 Image 1
    Cottage $370 / Nightly
    • 2 Bed
    • 1 Baths
    • (128)
    Woodstock, NY

    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

  • Property-6 Image 1
    Barn $507 / Nightly
    • 3 Bed
    • 2 Baths
    • (25) Exceptional
    Woodstock, NY

    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

  • Property-7 Image 1
    House $370 / Nightly
    • 3 Bed
    • 2 Baths
    • (55)
    Woodstock, NY

    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

  • Property-8 Image 1
    Cottage $221 / Nightly
    • 1 Bed
    • 1 Baths
    • (71) Excellent
    Woodstock, NY

    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

  • Property-9 Image 1
    Apartment $265 / Nightly
    • 1 Bed
    • 1 Baths
    • (107)
    Woodstock, NY

    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

  • Property-10 Image 1
    Studio $181 / Nightly
    • 2 Baths
    • (97)
    Woodstock, NY

    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

  • Property-11 Image 1
    Cottage $270 / Nightly
    • 1 Bed
    • 1 Baths
    • (108) Wonderful
    Woodstock, NY

    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

  • Property-12 Image 1
    House $583 / Nightly
    • 5 Bed
    • 4 Baths
    • (3) Exceptional
    Woodstock, NY

    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

  • Property-13 Image 1
    Apartment $280 / Nightly
    • 2 Bed
    • 1 Baths
    • (51) Wonderful
    Woodstock, NY

    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

  • Property-14 Image 1
    Cottage $265 / Nightly
    • 1 Baths
    • (19)
    Woodstock, NY

    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

  • Property-15 Image 1
    Lodge $216 / Nightly
    • 5 Bed
    • 500 Baths
    • (9)
    Woodstock, NY

    --------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

  • Property-16 Image 1
    House $2,188 / Nightly
    • 6 Bed
    • 8 Baths
    • (69) Wonderful
    Woodstock, NY

    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

  • Property-17 Image 1
    Cabin $179 / Nightly
    • 1 Bed
    • 1 Baths
    • (21) Excellent
    Woodstock, NY

    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

  • Property-18 Image 1
    House $448 / Nightly
    • 4 Bed
    • 4 Baths
    • (35) Wonderful
    Woodstock, NY

    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

  • Property-19 Image 1
    House $248 / Nightly
    • 2 Bed
    • 2 Baths
    • (21) Wonderful
    Woodstock, NY

    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

  • Property-20 Image 1
    Apartment $144 / Nightly
    • 1 Bed
    • 1 Baths
    • (9) Wonderful
    Woodstock, NY

    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

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Vacation Rental Filters are an easy way to help you personalize your search to find the ideal rental in Woodstock. Many accommodations in Woodstock provide "Non Smoking Only", there are 139, or there are 111 of Vacation Rentals in Woodstock with a "Biking", there are also 110 with "Hiking", which is another great reason to visit Woodstock.

We analyzed price data and rendered them in this graph, which shows vacation rental prices for the next twelve months in Woodstock. The most expensive month of the next 12 months is in July, where prices hit an average of $366 a night. In June, prices will hit an average low of $408 per night.