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, 249 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, 151 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

4.86 out of 5 average rating, 154 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 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 Mendon

4.96 out of 5 average rating, 26 reviews

Pico/ Killington chalet, minutes to the mountain

Welcome to our boutique style mountain chalet nestled in tall birch trees. Our fully equipped modern home is 10 mins to Pico and 15 minutes to the Killington access road. Whether you’re in VT to shred the Beast of the East or leaf peep the Green Mountains our home offers a cozy retreat for some time to relax between adventures. Close to breweries, orchards, hiking on the Appalachian Trail/Long Trail, and the convenience of Rutland. AND… We’re walking distance to pancakes and putt-putt =).

Guest favourite

Chalet in Fairlee

4.91 out of 5 average rating, 530 reviews

The Green Mountain Chalet

The atmosphere is rejuvenating in this spacious and unique Chalet with beautiful pastoral views! Stylishly built with gorgeous, exposed post and beam cathedral ceilings and decor with a unique style to host you a peaceful getaway. The kitchen has recently been updated with stylish subway tiles & quartz countertops! Min to Lake Fairlee & Lake Morey. If you’re inclined to hike, the Rivendell Trail System and Bald Top Mt. are just down the road. 25min drive Dartmouth College.

Guest favourite

Chalet in Royalton

4.93 out of 5 average rating, 169 reviews

Scandinavian design Chalet w/ private hiking trail

* NEW FROM 8 of NOVEMBER '24: a Goodland Wood Burning Hot tub*. 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 Stockbridge

4.96 out of 5 average rating, 126 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.

Guest favourite

Chalet in Killington

4.87 out of 5 average rating, 248 reviews

Large Chalet; Sauna, Hot Tub; Walk to Trail

Short walk (200 yds) to Homestretch ski trail at Killington ski mountain. Trail is weather dependent, from late Dec to mid-March. If the nearby trail is not open, it will not be available. Close to hiking/biking trails, golf, nightlife, rivers and lakes. Large open living space and lots of sleeping space makes our home comfortable for large groups. Driveway holds up to 5 cars. Enjoy relaxing in the hot tub, sauna or spending time by the fire.