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Woodstock: Vacation Rental By Owner

Search result 1 to 20 Of 103
  • Property-1 Image 1
    House $248 / Nightly
    • 2Bed
    • 2Baths
    • (18) 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-2 Image 1
    House $612 / Nightly
    • 4Bed
    • 2Baths
    • (67) Wonderful
    Woodstock, NY

    Experience Woodstock, NY and the Catskill Mountains while staying at our lovely four-bedroom home. Located on nearly three-acres, Our Woodstock House offers both... ...more

  • Property-3 Image 1
    House $549 / Nightly
    • 4Bed
    • 3Baths
    • (17)
    Woodstock, NY

    Pool will be open until September 29, 2019 Bright and airy Woodstock home with all the amenities you will need. Located only 4 minutes from the Village of... ...more

  • Property-4 Image 1
    House $747 / Nightly
    • 4Bed
    • 3Baths
    • (23) Exceptional
    Woodstock, NY

    Spacious, elegant, Woodstock Classic called a 'Jewel in Paradise' by one of our valued guests. (see reviews.) We pride ourselves on offering a home which is a... ...more

  • Property-5 Image 1
    Cottage Select Dates for Price
    • 2Bed
    • 1Baths
    • (6) Exceptional
    Woodstock, NY

    Snow has arrived! Ski and snowboard at Hunter, Belleayre and Windham! Mike and I have a large 1800’s cottage for rent. There are two bedrooms, a futon in the... ...more

  • Property-6 Image 1
    Apartment Select Dates for Price
    • 2Bed
    • 2Baths
    Woodstock, NY

    We offer a complete garden apartment with a separate entrance on the first level of our family home. The floor plan of the apartment has two connected bedrooms... ...more

  • Property-7 Image 1
    Guest House $156 / Nightly
    • 1Bed
    • 1Baths
    • (8) Excellent
    Woodstock, NY

    Perfect location between Woodstock and Bearsville. Charming 1 bedroom/1 bathroom apartment with spacious living room and kitchen. Your guest quarters is in a... ...more

  • Property-8 Image 1
    Cottage $243 / Nightly
    • 1Bed
    • 1Baths
    • (35)
    Woodstock, NY

    Enjoy a relaxing vacation in this quiet, yet walk-to-town one-bedroom cottage. The living room offers lots of natural light, comfortable seating, and air... ...more

  • Property-9 Image 1
    Cottage $309 / Nightly
    • 2Bed
    • 1Baths
    • (47)
    Woodstock, NY

    Treat yourself to a romantic getaway, personal retreat or creative sabbatical in your own private storybook cottage nestled in a 5-acre forest in Woodstock, the... ...more

  • Property-10 Image 1
    Barn $272 / Nightly
    • 1Bed
    • 1Baths
    • (35) Very Good
    Woodstock, NY

    The Field Studio is in a very convenient private place. Off Route 375 at the end of Hasbrouck Lane is the studio driveway that goes along a large field. As you go... ...more

  • Property-11 Image 1
    Cabin $347 / Nightly
    • 2Bed
    • 2Baths
    • (86) Wonderful
    Woodstock, NY

    Treat yourself to a romantic getaway or family retreat in your own private log cabin on Ohayo Mountain, just 1.5 miles from the center of Woodstock, the famous... ...more

  • Property-12 Image 1
    House Select Dates for Price
    • 3Bed
    • 2Baths
    • (13) Exceptional
    Woodstock, NY

    Picture yourself in an Arts-and-Crafts-style home, on 3.3 acres, just a short walk from Woodstock’s Village Green. We've owned it since 2002 and listed it in 2019... ...more

  • Property-13 Image 1
    Cabin Select Dates for Price
    • 1Bed
    • 1Baths
    • (66)
    Woodstock, NY

    Situated just 3 minutes from the vibrant center of Woodstock, this property feels so secluded that you'll forget how close to town you really are. Your guest... ...more

  • Property-14 Image 1
    House $528 / Nightly
    • 3Bed
    • 2Baths
    • (1) Exceptional
    Woodstock, NY

    This is a newly renovated architect's/artist's home featured in Icon Design Magazine Italy. The setting with a private waterfall bordering public preserves, as... ...more

  • Property-15 Image 1
    House $609 / Nightly
    • 4Bed
    • 3Baths
    • (13)
    Woodstock, NY

    - WE HAVE A WEEK MINIMUM IN SUMMER - POOL IS OPEN IN SUMMER MONTHS - HOT TUB IS OPEN MOST MONTHS This beautiful 2,000 sq. ft house is modern and clean. It sits... ...more

  • Property-16 Image 1
    House $198 / Nightly
    • 2Bed
    • 1Baths
    • (17) Excellent
    Woodstock, NY

    This fully-furnished house includes a master bedroom with a queen-size bed; a guest bedroom with two twin beds; a sectional sofa with queen size sleeper and a... ...more

  • Property-17 Image 1
    Apartment $484 / Nightly
    • 3Bed
    • 2Baths
    • (11) Exceptional
    Woodstock, NY

    A fabulous 3BR, 2Bath Suite to stay in Woodstock! Centrally located in the village, yet private, and steps to everything. BEST LOCATION TO ENJOY WALKING, HIKING,... ...more

  • Property-18 Image 1
    House $337 / Nightly
    • 3Bed
    • 2Baths
    • (1) Exceptional
    Woodstock, NY

    This is a true Woodstock home. 100-years-old with lots of windows and character. The house sits on 2 acres of beautiful trees, grass and a seasonal stream.... ...more

  • Property-19 Image 1
    Cottage $265 / Nightly
    • 1Baths
    • (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-20 Image 1
    Cabin Select Dates for Price
    • 2Bed
    • 2Baths
    • (5) Exceptional
    Woodstock, NY

    This home is a very special place; top of the mountain, abundant wildlife, secluded, southern exposure, and super cozy comfy. 10 min into Woodstock. House is... ...more

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 January, where prices hit an average of $301 a night. In December, prices will hit an average low of $299 per night.