Windham: Vacation Rental By Owner

Showing 20 Of 75 Vacation Rentals
  • Property-1 Image 1
    House Select Dates for Price
    • 9 Bed
    • 6 Baths
    Windham, NY

    Relax and enjoy time with friends and family in this beautiful mountainside retreat! Whole house is 9 bedrooms but is separated into 2 units, a 4 bedroom and a 5... ...more

  • Property-2 Image 1
    Chateau / Country House $508 / Nightly
    • 4 Bed
    • 2 Baths
    • (27) Wonderful
    Windham, NY

    This 4 bedroom, 2 full bathroom, charming tudor-style chalet was designed with an eye toward entertaining. The home has a large two and a half story great room... ...more

  • Property-3 Image 1
    House $540 / Nightly
    • 4 Bed
    • 4 Baths
    • (18)
    Windham, NY

    Welcome to your Windham Retreat! Enjoy incredibly easy access to some of the best skiing in New York. This home has all the extras and finishing touches that will... ...more

  • Property-4 Image 1
    Chalet $506 / Nightly
    • 4 Bed
    • 3 Baths
    • (48) Wonderful
    Windham, NY

    Welcome to Morning Star Vacation Home in Windham NY. We are Nestled in the heart of the Northern Catskill Mountains, this beautiful chalet home will enchant you... ...more

  • Property-5 Image 1
    House $717 / Nightly
    • 4 Bed
    • 4 Baths
    • (17) Exceptional
    Windham, NY

    Stunning Windham Log Cabin Retreat! Our spacious home has 4 bedrooms and 3 and 1/2 bathrooms. Sleeps 12 (1 King, 2 Queens, 3 bunk beds plus pull out queen... ...more

  • Property-6 Image 1
    Townhome $312 / Nightly
    • 4 Bed
    • 2 Baths
    • (31) Wonderful
    Windham, NY

    This townhome unit sleeps up to 12. There is bedroom with a double bed and a den/4th bedroom with a queen sofa bed on the ground floor. The full bathroom on this... ...more

  • Property-7 Image 1
    House Select Dates for Price
    • 6 Bed
    • 3 Baths
    • (1) Very Good
    Windham, NY

    Local wineries, delicious eateries, and all the beauty of the Catskill Mountains will be right at your fingertips at this lovely 6-bed, 3-bath family home. Along... ...more

  • Property-8 Image 1
    House Select Dates for Price
    • 4 Bed
    • 3 Baths
    • (9) Exceptional
    Windham, NY

    Our charming timber frame home offers a unique aesthetic appeal - a harmonious combination of rustic warmth and modern function. This mountain retreat offers... ...more

  • Property-9 Image 1
    House $1,004 / Nightly
    • 6 Bed
    • 3 Baths
    • (29) Excellent
    Windham, NY

    Among the nicest properties in Windham. Lovely large home nestled quietly on 12 usable acres with bucolic bridle paths joined to hiking trails. A true feel of... ...more

  • Property-10 Image 1
    House $633 / Nightly
    • 6 Bed
    • 3 Baths
    • (2) Exceptional
    Windham, NY

    Rustic cabin 1820 Farmhouse. Come walk Windham path, mountain bike or ski Windham mountain. Ski Hunter mountain or ride the zip lines. Enjoy the view of WINDHAM... ...more

  • Property-11 Image 1
    Condo Select Dates for Price
    • 2 Bed
    • 1 Baths
    • (2) Exceptional
    Windham, New York

    Get away from the hustle and bustle of city life with a retreat to this 2-bedroom, 1-bath Windham vacation rental! The condo has room for 4 to relax and feel at... ...more

  • Property-12 Image 1
    Condo Select Dates for Price
    • 2 Bed
    • 1 Baths
    Windham, New York

    Get outdoors in the Catskill Mountains with a trip to this 2-bedroom, 1-bathroom Windham vacation rental! Windham Mountain sits only 2.2 miles from the cozy condo... ...more

  • Property-13 Image 1
    House Select Dates for Price
    • 12 Bed
    • 10 Baths
    • (7) Exceptional
    Windham, NY

    A one-of-a-kind experience in the 'Gem of the Catskills' awaits at this spectacular Windham mansion. Spanning over 11,000 square feet, this massive vacation... ...more

  • Property-14 Image 1
    Townhome $1,544 / Nightly
    • 4 Bed
    • 2 Baths
    • (3) Exceptional
    Windham, NY

    Old-world charm meets modern luxury inside this 1901 converted firehouse, featuring 16-foot tin ceilings, a home theater system and a restored 1870’s Brunswick... ...more

  • Property-15 Image 1
    House $794 / Nightly
    • 5 Bed
    • 2 Baths
    • (1) Very Good
    Windham, NY

    Clear the calendar for a trip to the Catskills and stay at this spacious vacation rental property! With 5 bedrooms and 2 bathrooms, this house is perfect for... ...more

  • Property-16 Image 1
    Cabin $433 / Nightly
    • 5 Bed
    • 3 Baths
    • (84) Wonderful
    Windham, NY

    Tucked away on 110 acres of stunning Catskill Mountain landscape, this charming log cabin awaits any family looking for a mountain getaway. A beautiful and... ...more

  • Property-17 Image 1
    Estate $1,965 / Nightly
    • 4 Bed
    • 5 Baths
    • (61)
    Luxury Log Home with Ski Windham views Windham, NY

    Beautiful log home on 15 acres with amazing views of Ski Windham. This home has an outdoor hot tub and fire pit, as well as its own wine cellar on the bottom... ...more

  • Property-18 Image 1
    House Select Dates for Price
    • 7 Bed
    • 6 Baths
    Windham, NY

    This premium SKI-IN SKI-OUT property is located directly behind the Waffle Cabin and Ski School Meeting area with direct access to all ski lifts. Enjoy the... ...more

  • Property-19 Image 1
    Condo $196 / Nightly
    • 2 Bed
    • 2 Baths
    • (10) Wonderful
    Windham, NY

    HIDDEN GEM IN CATSKILLS START your Fabulous Windham Mountain Week on a MONDAY . .and Receive a $50 Windham Diner coupon!!!!!!!!! A/C Mountain Fresh Air... ...more

  • Property-20 Image 1
    Townhome $196 / Nightly
    • 2 Bed
    • 2 Baths
    • (10) Excellent
    Windham, NY

    SPACIOUS 2-STORY DOWNTOWN TOWNHOUSE; 12 ft Ceilings START your Fabulous Week in the Windham Mountains on a TUESDAY and receive a Windham Diner $50 coupon!... ...more

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Vacation Rental Filters are an easy way to help you personalize your search to find the ideal rental in Windham. Many accommodations in Windham provide "Non Smoking Only", there are 89, or there are 78 of Vacation Rentals in Windham with a "Children Welcome", there are also 71 with "Golf", which is another great reason to visit Windham.

We analyzed price data and rendered them in this graph, which shows vacation rental prices for the next twelve months in Windham. The most expensive month of the next 12 months is in July, where prices hit an average of $494 a night. In June, prices will hit an average low of $522 per night.