Chalet vacation rentals in Windsor County

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Top-rated chalet rentals in Windsor County

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Guest favorite

Chalet in Killington

4.83 out of 5 average rating, 235 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 favorite

Chalet in Stockbridge

4.93 out of 5 average rating, 175 reviews

Killington ski house winter MTbike -new jacuzzi

Killington Ski Area with access to snowmobile and mountain biking trails. This is a 3 bedroom, 2 bath upper unit duplex. with outdoor 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 too Fantastic unit check our review

Guest favorite

Chalet in West Fairlee

4.92 out of 5 average rating, 526 reviews

Hillcrest Manor of Vermont

A tranquil retreat tucked in the countryside of Vermont that sleeps 20, 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

Superhost

Chalet in Stockbridge

4.85 out of 5 average rating, 137 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, 145 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!

Guest favorite

Chalet in Woodstock

4.98 out of 5 average rating, 101 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 favorite

Chalet in Killington

4.98 out of 5 average rating, 101 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 favorite

Chalet in Plymouth

4.96 out of 5 average rating, 101 reviews

Ledges Unit: Hot Tub, two miles 2 Skyeship Gondola

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 favorite

Chalet in Mendon

5 out of 5 average rating, 23 reviews

Unique Luxury-Minutes to Skiing-Hidden Speakeasy

Luxury Ski Chalet in a GREAT location ❄️10 MINUTES TO ALL THE ACTION IN KILLINGTON ❄️5 MINUTES TO THE BASE OF PICO ❄️15 MINUTES TO THE K1 OR SKYSHIP GONDOLAS IN KILLINGTON ❄️SECRET BOOKCASE DOOR HIDING A LARGE, WELL-EQUIPPED SPEAKEASY ❄️NO CLEANING FEE ❄️MASSIVE THEMED KIDS ROOM ❄️TWO MASTER BEDROOMS WITH PRIVATE BATHROOM ACCESS ❄️THOUGHTFUL AMENITIES FOR LARGE FAMILIES SEEKING LUXURY AND FUN ❄️EV CHARGER ❄️INCREDIBLY COMFORTABLE BEDS AND LINENS ❄️CONVENIENT BUT REMOTE

Guest favorite

Chalet in Killington

4.96 out of 5 average rating, 77 reviews

Modern and Idyllic Country Getaway Mendon

Beautiful mountain chalet built in 1953 and remodeled in 2016. Nestled at the end of a long driveway, off Route 4 at the base of Pico Mountain. 15 minutes to Killington Mountain and Rutland, 20 to Woodstock. House sits on 50 acres of woods with private hiking and cross-country skiing trails for guests to use. Huge open living room, opposite the den has windows on three sides, is filled with light and cush seating for lounging while bird and bear watching!

Guest favorite

Chalet in Royalton

4.93 out of 5 average rating, 149 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 favorite

Chalet in Stockbridge

4.95 out of 5 average rating, 110 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.