Compare Windsor Chalets

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Featured Windsor 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.

Hotel Options in Windsor

    Life House Berkshires

    Life House Berkshires

    194 Pittsfield Rd, Lenox, MA
    The price is $115 per night from May 4 to May 5
    $115
    includes taxes & fees
    $103 per night
    May 4 - May 5
    9/10 Wonderful! (574 reviews)
    Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

    Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

    190 Meadow Street, South Lee, MA
    The price is $134 per night from May 14 to May 15
    $134
    includes taxes & fees
    $120 per night
    May 14 - May 15
    9/10 Wonderful! (627 reviews)
    The Yankee, Trademark Collection by Wyndham

    The Yankee, Trademark Collection by Wyndham

    461 Pittsfield Rd, Lenox, MA
    The price is $120 per night from May 4 to May 5
    $120
    includes taxes & fees
    $107 per night
    May 4 - May 5
    9/10 Wonderful! (1,001 reviews)

Chalets

Book the best chalets in Windsor
Take a break from reality and kick back in a Windsor 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 Windsor. 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 Windsor has to offer.

Bring the whole group, because you’ll find plenty of space to spread out at Windsor 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.

Windsor Chalets essential information

Accommodation
4 Chalets
Lowest Price
$115
Highest Price
$134
Popular accommodation
Sunny Chalet Nestled in the Woods of Ashfield, Little Longbow Lakefront Chalet, SRC-Hudson Valley/Berkshires Cultural Corridor, Secluded Mountain Chalet