Compare Windsor Chalets

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Featured Chalets in Windsor

The Whimsical Chalet is a lovely cape on acres. Private setting less than 10 minutes to skiing.

The Whimsical Chalet is a lovely cape on acres. Private setting less than 10 minutes to skiing.

Mount Holly VT
At this chalet, guests have access to features like laundry facilities.
Kitchen
Washer
Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails

Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails

Ludlow VT
At this chalet, guests have access to an arcade/game room, laundry facilities, and a garden. This family-friendly chalet also has barbecue grills.
Fabulous 4-bedroom chalet in tranquil Killington getaway with gorgeous Hot tub

Fabulous 4-bedroom chalet in tranquil Killington getaway with gorgeous Hot tub

Killington VT
$430 nightly
The price is $485 total per night
$485 total
Mar 15 - Mar 16
Total with taxes and fees
Guests staying at this chalet enjoy a hot tub, laundry facilities, and barbecue grills.
Hot Tub
Kitchen
Bigelow Chalet at Killington: 8BR/4.5 BA Pet Friendly Home w/ Hot Tub, Fireplace.

Bigelow Chalet at Killington: 8BR/4.5 BA Pet Friendly Home w/ Hot Tub, Fireplace.

Killington VT
This chalet features a hot tub, an arcade/game room, and laundry facilities. This smoke-free chalet also has barbecue grills.
Black Dog Lodge - Ski Chalet centered between Okemo and Killington Mt.

Black Dog Lodge - Ski Chalet centered between Okemo and Killington Mt.

Plymouth VT
Guests staying at this chalet have access to laundry facilities, a garden, and barbecue grills.
Ski In/Out Luxury 8BR Okemo Chalet on Sachem Trail Sleeps 22 Adults

Ski In/Out Luxury 8BR Okemo Chalet on Sachem Trail Sleeps 22 Adults

ludlow VT
This chalet offers ski-in/ski-out access, an arcade/game room, and laundry facilities. Other amenities at this ski chalet include a garden and barbecue grills.
BearHaus-Fireplace, HUGE indoor Hot Tub, Sleeps 14

BearHaus-Fireplace, HUGE indoor Hot Tub, Sleeps 14

Killington VT
$900 nightly
The price is $1,017 total per night
$1,017 total
Mar 17 - Mar 18
Total with taxes and fees
Guests staying at this chalet enjoy a hot tub, laundry facilities, and barbecue grills. This family-friendly chalet also has a garden.
Killington Chalet - Great Space and Location!

Killington Chalet - Great Space and Location!

Killington VT
Guests staying at this chalet enjoy a hot tub, laundry facilities, and barbecue grills. This smoke-free chalet also has a garden.
The Whimsical Chalet

The Whimsical Chalet

2.5 out of 5
1579 Healdville Rd. Mount Holly VT
This chalet features a gym and laundry facilities. If you drive, take advantage of free parking.
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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

    White River Inn and Suites

    White River Inn and Suites

    91 Ballardvale Drive White River Junction VT
    $121 nightly
    The price is $133 total per night from Mar 22 to Mar 23
    $133 total
    Mar 22 - Mar 23
    Total with taxes and fees
    7/10 Good! (1,006 reviews)
    Align Inn Vermont

    Align Inn Vermont

    5817 Woodstock Rd Quechee VT
    $119 nightly
    The price is $131 total per night from Mar 11 to Mar 12
    $131 total
    Mar 11 - Mar 12
    Total with taxes and fees
    9.4/10 Exceptional! (1,142 reviews)
    Fireside Inn & Suites West Lebanon

    Fireside Inn & Suites West Lebanon

    25 Airport Road West Lebanon NH
    $144 nightly
    The price is $157 total per night from Mar 17 to Mar 18
    $157 total
    Mar 17 - Mar 18
    Total with taxes and fees
    8.2/10 Very Good! (1,011 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
46 Chalets
Lowest Price
$131
Highest Price
$1,017
Popular accommodation
The Whimsical Chalet is a lovely cape on acres. Private setting less than 10 minutes to skiing., Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails, Fabulous 4-bedroom chalet in tranquil Killington getaway with gorgeous Hot tub, Bigelow Chalet at Killington: 8BR/4.5 BA Pet Friendly Home w/ Hot Tub, Fireplace., Black Dog Lodge - Ski Chalet centered between Okemo and Killington Mt. , Ski In/Out Luxury 8BR Okemo Chalet on Sachem Trail Sleeps 22 Adults, BearHaus-Fireplace, HUGE indoor Hot Tub, Sleeps 14, Killington Chalet - Great Space and Location!, The Whimsical Chalet