Compare Windsor Chalets

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Featured Chalets in Windsor

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
$390 nightly
The price is $441 total per night
$441 total
Aug 20 - Aug 21
Total with taxes and fees
Guests staying at this chalet enjoy a hot tub, laundry facilities, and barbecue grills.
Ski On, Ski off Okemo Trailside Appartment, Sleeps 6/ $550per night,

Ski On, Ski off Okemo Trailside Appartment, Sleeps 6/ $550per night,

Ludlow VT
Guests of this chalet enjoy access to ski-in/ski-out access, laundry facilities, and barbecue grills.
Kitchen
Washer
Spacious 5-bedroom chalet with AC and WiFi in charming Chester

Spacious 5-bedroom chalet with AC and WiFi in charming Chester

Chester VT
Guests staying at this chalet enjoy a hot tub, laundry facilities, and barbecue grills.
Hot Tub
Kitchen
3-bedroom, 2-bath chalet, minutes from I-89 Dartmouth Medical Center

3-bedroom, 2-bath chalet, minutes from I-89 Dartmouth Medical Center

lebanon NH
Guests staying at this chalet have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
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 barbecue grills and a garden.
Kitchen
Washer
Gorgeous Ski Chalet with Game Room & Hot Tub on Okemo Mt. under 1 mile to base!

Gorgeous Ski Chalet with Game Room & Hot Tub on Okemo Mt. under 1 mile to base!

Ludlow VT
At this chalet, guests have access to a hot tub, an arcade/game room, and laundry facilities. Other amenities at this family-friendly chalet include barbecue grills and a garden.
Hot Tub
Kitchen
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo

"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo

Plymouth VT
Guests of this chalet enjoy a hot tub, an arcade/game room, and laundry facilities. Other amenities at this golf chalet include barbecue grills and a garden.
Woodbridge Inn · 6BR Historic Charm✦Riverfront✦Hot Tub✦Close to Ski

Woodbridge Inn · 6BR Historic Charm✦Riverfront✦Hot Tub✦Close to Ski

Woodstock VT
This chalet features a hot tub, an arcade/game room, and laundry facilities. Other amenities at this family-friendly chalet include a garden and barbecue grills.
Charming pet-friendly retreat in the Vermont woods

Charming pet-friendly retreat in the Vermont woods

Plymouth VT
Guests staying at this chalet have access to laundry facilities, barbecue grills, and a garden.
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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

    Fireside Inn & Suites West Lebanon

    Fireside Inn & Suites West Lebanon

    25 Airport Road West Lebanon NH
    $156 nightly
    The price is $169 total per night from Sep 13 to Sep 14
    $169 total
    Sep 13 - Sep 14
    Total with taxes and fees
    8.4/10 Very Good! (1,012 reviews)
    Align Inn Vermont

    Align Inn Vermont

    5817 Woodstock Rd Quechee VT
    $90 nightly
    The price is $99 total per night from Aug 25 to Aug 26
    $99 total
    Aug 25 - Aug 26
    Total with taxes and fees
    9.4/10 Exceptional! (1,290 reviews)
    Woodstock Inn & Resort

    Woodstock Inn & Resort

    Fourteen The Green Woodstock VT
    $449 nightly
    The price is $494 total per night from Sep 7 to Sep 8
    $494 total
    Sep 7 - Sep 8
    Total with taxes and fees
    9.4/10 Exceptional! (598 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
$99
Highest Price
$494
Popular accommodation
Fabulous 4-bedroom chalet in tranquil Killington getaway with gorgeous Hot tub, Ski On, Ski off Okemo Trailside Appartment, Sleeps 6/ $550per night,, Spacious 5-bedroom chalet with AC and WiFi in charming Chester, 3-bedroom, 2-bath chalet, minutes from I-89 Dartmouth Medical Center, Ski In/Out Luxury 8BR Okemo Chalet on Sachem Trail Sleeps 22 Adults, Gorgeous Ski Chalet with Game Room & Hot Tub on Okemo Mt. under 1 mile to base!, "The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo, Woodbridge Inn · 6BR Historic Charm✦Riverfront✦Hot Tub✦Close to Ski, Charming pet-friendly retreat in the Vermont woods