Compare Windsor Chalets

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Featured Chalets in Windsor

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

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

Woodstock VT
Guests staying at this chalet have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Modern 7Bd/3Ba Mountain Chalet w/ Hot tub, 3 minutes from Okemo

Modern 7Bd/3Ba Mountain Chalet w/ Hot tub, 3 minutes from Okemo

Ludlow VT
At this chalet, guests have access to features like an arcade/game room and laundry facilities.
Dryer
Outdoor Space
Cozy chalet minutes from Okemo Mtn & VAST

Cozy chalet minutes from Okemo Mtn & VAST

Mount Holly VT
At this chalet, guests have access to features like laundry facilities. This smoke-free chalet also has barbecue grills.
Kitchen
Washer
BearVaria AC, Hot Tub, Fire Pit Grill, FrisbeeGolf

BearVaria AC, Hot Tub, Fire Pit Grill, FrisbeeGolf

Killington VT
$487 nightly
The price is $551 total per night
$551 total
May 25 - May 26
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.
Hot Tub
Kitchen
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.
Hot Tub
Kitchen
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.
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 a garden and barbecue grills.
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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
    $143 nightly
    The price is $155 total per night from May 31 to Jun 1
    $155 total
    May 31 - Jun 1
    Total with taxes and fees
    8.2/10 Very Good! (1,001 reviews)
    Killington Mountain Lodge, Tapestry Collection by Hilton

    Killington Mountain Lodge, Tapestry Collection by Hilton

    2617 Killington Rd Killington VT
    $130 nightly
    The price is $143 total per night from May 25 to May 26
    $143 total
    May 25 - May 26
    Total with taxes and fees
    7.4/10 Good! (1,000 reviews)
    Align Inn Vermont

    Align Inn Vermont

    5817 Woodstock Rd Quechee VT
    $119 nightly
    The price is $131 total per night from May 24 to May 25
    $131 total
    May 24 - May 25
    Total with taxes and fees
    9.4/10 Exceptional! (1,191 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
$551
Popular accommodation
Ski On, Ski off Okemo Trailside Appartment, Sleeps 6/ $550per night,, The Whimsical Chalet is a lovely cape on acres. Private setting less than 10 minutes to skiing., Woodbridge Inn · 6BR Historic Charm✦Riverfront✦Hot Tub✦Close to Ski, Modern 7Bd/3Ba Mountain Chalet w/ Hot tub, 3 minutes from Okemo, Cozy chalet minutes from Okemo Mtn & VAST, BearVaria AC, Hot Tub, Fire Pit Grill, FrisbeeGolf, Killington Chalet - Great Space and Location!, 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!