Chalet holiday 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.

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Guest favourite

Chalet in Killington

4.84 out of 5 average rating, 251 reviews

Killington Chalet - Hot Tub, Sauna, Boot Dryer

The Killington Chalet is your ideal vacation rental in the Green Mountains. It's the Right side of a duplex, perfect for families, couples, and groups. Located just off Killington Rd, it offers a secluded retreat near slopes, restaurants, and outdoor activities. Enjoy skiing, boarding, mountain biking, and more. Features include hot tub, sauna, boot dryer, wood stove, fire pit, and a fully equipped kitchen. Fresh linens, towels, and toiletries provided. Book for a memorable stay in every season!

Guest favourite

Chalet in Mount Holly

4.97 out of 5 average rating, 152 reviews

Charming Summit View Chalet near Okemo and Lakes

Welcome to Mount Holly! Our chalet is a 3-level, 3-bedroom, 2-full bathroom home slightly northwest of Okemo. A bright, comfortable home with large deck & mountain views. 4 miles to skiing and lakes! 2 Queen beds & a bunk w/full & twin bed - sleeps 7 people max. Large laundry room with full size washer/dryer. Full kitchen. Sits on private, 1-acre wooded lot in quiet wooded neighborhood. Short drive to restaurants, hikes, lakes, cheese shop & local farm. Local helpers in the neighborhood.

Guest favourite

Chalet in Stockbridge

4.92 out of 5 average rating, 181 reviews

Killington ski house winter MTbike -new jacuzzi

Killington Ski Area with access to snowmobile mountain biking trails. This 3 bedroom, 2 bath upper unit duplex. with outdoor private Jacuzzi open year round with barbecue on very nice decks for those nicer days , snow mobile right from the house , on the tweed valley vast trails , in the summer mountain bike on the green mountain trail system right on our mountain keep us in mind for the summer event like the spartan race and the peak series Mt biking events Fantastic unit check our reviews

Superhost

Chalet in Stockbridge

4.84 out of 5 average rating, 159 reviews

Vermont Chalet

Killington Skiing, Pico Peak, Sugar Bush, Mad River are all within distance. Killington is 14 miles away. Fall folliage is fabulous; kitchen well equipped; very light and lovingly cared for. Spring and summer are just as wonderful. I am walking distance to the White River where there is canoeing, tubing and swimming. Within walking distance is the Gaysville Campgrounds. Here you'll find river access to a fabulous swimming hole in the White River as well as trails to explore or walk your dog.

Superhost

Chalet in Killington

4.9 out of 5 average rating, 162 reviews

Kingsbrook: Chalet w Sauna, Hot Tub, AC!

Located off East Mountain Road, on a secluded dead end street, just minutes from your choice of the Killington base lodges. There is access to a ski/hiking trail at the end of our street (1/2 mile from the house), and we're surrounded by hiking and biking trails. The house is great for large groups and families, as there are 2 separate living areas (kids like to hang out in the lower family room with large screen TV and games). Very strong and fast internet. Now with AC for summer getaways!

Top guest favourite

Chalet in Woodstock

4.98 out of 5 average rating, 105 reviews

Falcon House: VT Chalet w/Sauna, Bike to Village

Welcome to Falcon House! A modern VT chalet w/sauna at the edge of a 60 acre forest ∙ Outdoor Finnish sauna, shower, yoga platform & hiking trails ∙ 5 min to Woodstock village, 20 min to ski Killington ∙ Spotlessly clean, tastefully furnished, well stocked with thoughtful amenities ∙2 bedrooms, 2 full baths. Lofted king master has ensuite +Lower level den w/double futon ∙ Chefs kitchen, fireplace, 2 TVs & WiFi ∙ Brookside deck w/BBQ & dining ∙Follow Falcon House on Social @falcon_house_vt

Guest favourite

Chalet in Killington

5 out of 5 average rating, 126 reviews

Air Cond! Yard! 6BR, 12Bed, 3BA, Hot Tub, 5 stars!

2 Miles to resort! CEDARWALK at Killington, a luxury 6 BR, (12 beds) 3 BA home, with AC, Heart of Killington, three levels, 2 living rooms, great yard! 6/7 person HOT TUB on the deck with tons of privacy, Cathedral ceilings, huge Windows for great views, open living spaces! Perfect for entertaining. Renovated inside and out with upscale decor and comfortable beds. bluetooth SONOS sound. Certified with Vermont Fire Safety. Whole house water filtration. Cedarwalk Killington, killingtonLIFE

Guest favourite

Chalet in Killington

4.96 out of 5 average rating, 109 reviews

4BR/3BA ★ hot tub, sauna, billiards, A/C, & grill!

KILLINGTIME CABIN blends privacy with proximity!! Our 2,600 sq ft chalet is PERFECT for groups traveling with friends & family, with plenty of space for all. 4BR/3BA, large common areas, fieldstone fireplace, spacious kitchen, private deck, Weber grill, and finished walkout lower level with billiards, ski boot dryer, sauna, and hot tub for the ULTIMATE in après-ski luxury. Fast 200MB WiFi and 125+ channel cable TV. Bluetooth sound systems on both levels. Have a BLAST with your loved ones!!

Guest favourite

Chalet in Plymouth

4.95 out of 5 average rating, 118 reviews

Ledges Unit:1 mile to F&W Summer Camp w/ HOT TUB

The Ledges Unit at Killington’s Brookside Manor is a freshly renovated home away from home just 2 miles from Killington’s Skyeship Gondola. It is only 15 minutes from Killington’s main base area and 20 minutes to Okemo. The Ledges is a 2 story chalet in a 4 unit building. The 1st floor has a kitchen, living room with a large stone mantel and wood stove, dining room, and full bathroom. The 2nd floor has 4 bedrooms and bathroom. The other 3 listings at this location are rented separately.

Guest favourite

Chalet in Royalton

4.94 out of 5 average rating, 174 reviews

Scandinavian design Chalet w/ private hiking trail

* NEW* Starting mid-June, you can conveniently charge your electric vehicle during your stay This bright, well-designed Scandinavian-style chalet is the perfect cozy retreat. Nestled in the woods on a plot of 20+ acres, it offers scenic views and a private hiking trail leading to beautiful vistas, transforming into a winter wonderland for skiing adventures, a summer paradise for outdoor relaxation, and a vibrant canvas for leaf peeping during Vermont's stunning fall foliage season.

Guest favourite

Chalet in West Fairlee

4.92 out of 5 average rating, 545 reviews

Hillcrest Manor of Vermont

A tranquil retreat tucked in the countryside of Vermont, just 20 min from Dartmouth! Conveniently located minutes from LakeFairlee & LakeMorey. Rejuvenate yourself at this relaxing getaway surrounded by the pristine forests & wildlife of New England. Enjoy breathtaking mountainviews on a spacious deck with your loved ones on a large property with stunning rolling hills. 4 bedrooms, 2 full bathrooms, a basketball/tennis court, foosball, updated appliances, & fully stocked kitchen

Guest favourite

Chalet in Stockbridge

4.96 out of 5 average rating, 130 reviews

Gnome Home Mountain Ski Chalet w/Sauna Killington

Mountaintop Chalet perched in the heart of Green Mountains. Enjoy true mountain living all year long 25m to Killington, White River access minutes from home, abundance of hiking trails, and golf courses. Central to Killington, Rochester, & Woodstock. After your adventures, return to a welcoming & comfortable home with beautiful views from every room, multiple decks, new! fireplace, & sauna, and plenty of special touches to help you unwind and relax.