Compare Windham Chalets

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Featured Windham Chalets

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Windham Ski Accommodation

    Hotel Vienna

    Hotel Vienna

    107 State Route 296, Windham, NY
    The price is $137 per night from May 12 to May 13
    $137
    per night
    May 12 - May 13
    9/10 Wonderful! (351 reviews)
    Winwood Inn & Condominiums

    Winwood Inn & Condominiums

    5220 NY-23, Windham, NY
    The price is $139 per night from Apr 21 to Apr 22
    $139
    per night
    Apr 21 - Apr 22
    8.4/10 Very Good! (270 reviews)
    Albergo Allegria Hotel & Breakfast Restaurant

    Albergo Allegria Hotel & Breakfast Restaurant

    43 State Route 296, Windham, NY
    The price is $125 per night from Apr 21 to Apr 22
    $125
    per night
    Apr 21 - Apr 22
    9.6/10 Exceptional! (230 reviews)
    The Thompson House

    The Thompson House

    19 Rt. 296, Windham, NY
    8.2/10 Very Good! (55 reviews)
    Antique Rose Inn Windham

    Antique Rose Inn Windham

    326 State Route 296, Windham, NY
    The price is $130 per night from Apr 22 to Apr 23
    $130
    per night
    Apr 22 - Apr 23
    9/10 Wonderful! (108 reviews)
    Georgian Garden Inn

    Georgian Garden Inn

    5159 state route 23, Windham, NY
    8.8/10 Excellent! (27 reviews)
    Beds on Clouds

    Beds on Clouds

    5320 Main Street, Windham, NY
    The price is $171 per night from Apr 22 to Apr 23
    $171
    per night
    Apr 22 - Apr 23
    7.4/10 Good! (64 reviews)

Hotel Options in Windham

    Hotel Vienna

    Hotel Vienna

    107 State Route 296, Windham, NY
    The price is $137 per night from May 12 to May 13
    $137
    per night
    May 12 - May 13
    9/10 Wonderful! (351 reviews)
    Winwood Inn & Condominiums

    Winwood Inn & Condominiums

    5220 NY-23, Windham, NY
    The price is $139 per night from Apr 21 to Apr 22
    $139
    per night
    Apr 21 - Apr 22
    8.4/10 Very Good! (270 reviews)
    Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter

    Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter

    Windham
    The price is $1,250 per night from Apr 21 to Apr 22
    $1,250
    per night
    Apr 21 - Apr 22
    10/10 Exceptional! (125 reviews)

Chalets

Book the best chalets in Windham
Take a break from reality and kick back in a Windham chalet on your next vacation. Stay right in the middle of all the action, but feel like you’re miles away. Be as active or as relaxed as you want. Your chalet is truly yours. No one can tell you what to do on your chalet stay—and it’s the best way to enjoy a getaway.

Get the most from your chalet stay
You’ll make incredible new memories at chalets in Windham. They look great in your photos, with sunning backdrops and cozy touches like fireplaces and exposed beam ceilings. Wake up to light streaming through your big picture window and admire your incredible view. Don’t just look at the great outdoors, though. Get out there and experience all that Windham has to offer.

Bring the whole group, because you’ll find plenty of space to spread out at Windham chalet houses. Whether you use all those bedrooms for the kids or for your crazy crew, you can settle in quickly thanks to chalets’ convenient amenities. Whip up a meal in no time in the kitchen or kitchenette, or whip out your phone to call for delivery. Cozy up to the fire, or fire up the blender for some drinks. When you’ve got a chalet, it’s going to be good day.

Windham Chalets essential information

Accommodation
32 Chalets
Lowest Price
$125
Highest Price
$1,250
Popular accommodation
Mountain Chalet with Breathtaking Panoramic Views, Romantic Luxury Chalet With Private Pool, Rustic Mountain view Cabin 5 mins to Ski Area!, HotTub and 200Mbps WiFi; work from home paradise, Wonderful Belleayre Cabin, Charming Log Chalet w/ huge deck, pool & bonus garage loft on 17 secluded acres , A-frame Chalet w/ OUTDOOR TV & HOT TUB; fire pit, pool table, playground & more!, Beautiful Chalet, mins to Hunter/Windham slopes, Never Lonesome Woodland Valley: Cozy 2bd Cottage!, Big Indian near Full Moon Resort Spillian Onteora Mountain House Ski Belleayre