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 $139 per night from May 22 to May 23
    $139
    includes taxes & fees
    $129 per night
    May 22 - May 23
    9.2/10 Wonderful! (555 reviews)
    Winwood Inn & Condominiums

    Winwood Inn & Condominiums

    5220 NY-23, Windham, NY
    The price is $150 per night from May 4 to May 5
    $150
    includes taxes & fees
    $139 per night
    May 4 - May 5
    8.6/10 Excellent! (321 reviews)
    Albergo Allegria Hotel & Breakfast Restaurant

    Albergo Allegria Hotel & Breakfast Restaurant

    43 State Route 296, Windham, NY
    The price is $173 per night from May 4 to May 5
    $173
    includes taxes & fees
    $160 per night
    May 4 - May 5
    9.6/10 Exceptional! (258 reviews)
    Antique Rose Inn Windham

    Antique Rose Inn Windham

    326 State Route 296, Windham, NY
    9/10 Wonderful! (118 reviews)
    Georgian Garden Inn

    Georgian Garden Inn

    5159 state route 23, Windham, NY
    9/10 Wonderful! (28 reviews)
    Beds on Clouds

    Beds on Clouds

    5320 Main Street, Windham, NY
    The price is $222 per night from May 3 to May 4
    $222
    includes taxes & fees
    $206 per night
    May 3 - May 4
    7.4/10 Good! (67 reviews)

Hotel Options in Windham

    Hotel Vienna

    Hotel Vienna

    107 State Route 296, Windham, NY
    The price is $139 per night from May 22 to May 23
    $139
    includes taxes & fees
    $129 per night
    May 22 - May 23
    9.2/10 Wonderful! (555 reviews)
    Eastwind Windham

    Eastwind Windham

    5088 NY-23, Windham, NY
    The price is $214 per night from May 3 to May 4
    $214
    includes taxes & fees
    $199 per night
    May 3 - May 4
    9.2/10 Wonderful! (52 reviews)
    Wylder Hotel Windham

    Wylder Hotel Windham

    19 New York 296, Windham, NY
    The price is $230 per night from May 4 to May 5
    $230
    includes taxes & fees
    $213 per night
    May 4 - May 5
    8.2/10 Very Good! (54 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
54 Chalets
Lowest Price
$139
Highest Price
$230
Popular accommodation
1 Mile From Ski Slope and Festivals - 125 Nightly Fee, Stunning Catskills Cabin Getaway, facing BelleAyre, Mountain Chalet with Breathtaking Panoramic Views, Lakefront on the quiet side of main lake!, Chalet w/Covered HOT TUB & OUTDOOR TV; fire pit, pool table, trail & playground!, Beautiful Windham Chalet 2 minutes to Town and the Mountain, Rustic Mountain view Cabin 5 mins to Ski Area!, HotTub and 200Mbps WiFi; work from home paradise, Wonderful Belleayre Cabin, Beautiful Chalet, mins to Hunter/Windham slopes