Compare Windsor Chalets

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Featured Chalets in Windsor

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
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, barbecue grills, and a garden.
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.
Kitchen
Washer
Cozy Creekside Chalet centrally located near 4 ski resorts

Cozy Creekside Chalet centrally located near 4 ski resorts

Weston VT
Guests staying at this chalet have access to laundry facilities, a garden, and barbecue grills.
South View Chalet!

South View Chalet!

Killington VT
Guests staying at this chalet enjoy a gym, a sauna, and a hot tub. Other amenities at this family-friendly chalet include an arcade/game room, laundry facilities, and barbecue grills.
Mountain View Chalet Fabulous views from the hot tub with large entertaining area just off Killington Road

Mountain View Chalet Fabulous views from the hot tub with large entertaining area just off Killington Road

Killington VT
At this chalet, guests have access to features like laundry facilities.
Kitchen
Washer
Newly Renovated Rustic style home w/luxury bathrooms & mountain views, Sereni

Newly Renovated Rustic style home w/luxury bathrooms & mountain views, Sereni

Mount Holly VT
At this chalet, guests have access to features like laundry facilities. This smoke-free chalet also has barbecue grills.
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.
Cozy 4bd - Ski Okemo, Killington, Magic & Bromley

Cozy 4bd - Ski Okemo, Killington, Magic & Bromley

Chester VT
Guests staying at this chalet have access to 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

    Killington Mountain Lodge, Tapestry Collection by Hilton

    Killington Mountain Lodge, Tapestry Collection by Hilton

    2617 Killington Rd Killington VT
    $173 nightly
    The price is $191 total per night from Mar 1 to Mar 2
    $191 total
    Mar 1 - Mar 2
    Total with taxes and fees
    7.2/10 Good! (1,003 reviews)
    Align Inn Vermont

    Align Inn Vermont

    5817 Woodstock Rd Quechee VT
    $120 nightly
    The price is $132 total per night from Feb 5 to Feb 6
    $132 total
    Feb 5 - Feb 6
    Total with taxes and fees
    9.4/10 Exceptional! (1,098 reviews)
    Pointe at Castle Hill Resort

    Pointe at Castle Hill Resort

    2940 State Route 103 Cavendish VT
    $142 nightly
    The price is $154 total per night from Mar 1 to Mar 2
    $154 total
    Mar 1 - Mar 2
    Total with taxes and fees
    8.8/10 Excellent! (967 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
$132
Highest Price
$191
Popular accommodation
Killington Chalet - Great Space and Location!, Black Dog Lodge - Ski Chalet centered between Okemo and Killington Mt. , Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails, Cozy Creekside Chalet centrally located near 4 ski resorts, South View Chalet!, Mountain View Chalet Fabulous views from the hot tub with large entertaining area just off Killington Road, Newly Renovated Rustic style home w/luxury bathrooms & mountain views, Sereni, Gorgeous Ski Chalet with Game Room & Hot Tub on Okemo Mt. under 1 mile to base!, Cozy 4bd - Ski Okemo, Killington, Magic & Bromley