
Chalet vacation rentals in Windsor County
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Top-rated chalet rentals in Windsor County
Guests agree: these chalets are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Windsor County chalet rentals
Family-friendly chalet rentals

Newly Renovated Killington Chalet

Charming Family Ski Chalet 5 min from Okemo/JG

Cozy 4bd After Chalet - Ski Vermont

Tranquil Brookside Retreat w/Hot Tub

Cheerful 4-bedroom Chalet near popular Ski slopes

Charming Lakefront House

Charming chalet 5 min Bromley 20 min Stratton

Hawk House
Luxury chalet rentals

5BR Chalet in Historic Town bet Killington & Okemo

Private Mountain Sanctuary | 15 Min to Killington

Secret Speakeasy-Hot Tub-15 Mins to Killington

Mountain Chalet + HOT TUB

Okemo Mountain-Newly Renovated w AC, hottub, WiFi

BENT TREE Vermont, Mtn Chalet 25 min to Killington

Vintage 70s A frame - Big Hot Tub - 7 min from K1

PRIME location w/HOT TUB! Gut Renovated 6 BR Home!
Destinations to explore
- Rentals with lake access Windsor County
- Condo rentals Windsor County
- Waterfront rentals Windsor County
- Rentals with breakfast Windsor County
- Guesthouse rentals Windsor County
- House rentals Windsor County
- Private suite rentals Windsor County
- Villa rentals Windsor County
- Pet-friendly rentals Windsor County
- Rentals with outdoor seating Windsor County
- Rentals with an accessible height toilet Windsor County
- Rentals with a fireplace Windsor County
- Rentals with a kayak Windsor County
- Fitness-friendly rentals Windsor County
- Cabin rentals Windsor County
- Rentals with a patio Windsor County
- Farmstay rentals Windsor County
- Hotel rentals Windsor County
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- Bed and breakfasts Windsor County
- Rentals with pools Windsor County
- Rentals with an accessible height bed Windsor County
- Ski-in/ski-out rentals Windsor County
- Tiny house rentals Windsor County
- Rentals with an EV charger Windsor County
- Apartment rentals Windsor County
- Rentals with a hot tub Windsor County
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- Rentals with a washer and dryer Windsor County
- Rentals with a sauna Windsor County
- Chalet rentals Vermont
- Chalet rentals United States
- Stratton Mountain
- Okemo Mountain Resort
- Monadnock State Park
- Pats Peak Ski Area
- Magic Mountain Ski Resort
- Fort Ticonderoga
- Tenney Mountain Resort
- Stratton Mountain Resort
- Ragged Mountain Resort
- Mount Snow Ski Resort
- Dartmouth Skiway
- Pico Mountain Ski Resort
- Dorset Field Club
- Hooper Golf Course
- Hildene, The Lincoln Family Home
- Crotched Mountain Ski and Ride
- Lucky Bugger Vineyard & Winery
- Autumn Mountain Winery
- Ekwanok Country Club
- Fox Run Golf Club
- Whaleback Mountain
- Montshire Museum of Science
- Northeast Slopes Ski Tow
- Brattleboro Ski Hill
- Things to do Windsor County
- Food and drink Windsor County
- Things to do Vermont
- Food and drink Vermont
- Nature and outdoors Vermont
- Things to do United States
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