Chalet vacation rentals in Windsor County

Find and book unique chalets on Airbnb

Top-rated chalet rentals in Windsor County

Guests agree: these chalets are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

Chalet in Killington

5.0 out of 5 average rating, 117 reviews

Luxury, AC, 6 BR, 12 Beds, 3 Bath, Hot Tub, Yard

CEDARWALK at Killington, a luxury 6 BR, (12 beds) 3 BA home, with AC, for up to 14 people. 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

Nov 5 – 12

R19,459 ZAR per night

Superhost

Chalet in Stockbridge

4.93 out of 5 average rating, 168 reviews

Killington spring ski - 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

Oct 7 – 14

R5,885 ZAR per night

Guest favorite

Chalet in West Fairlee

4.9 out of 5 average rating, 506 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

Nov 18 – 25

R12,145 ZAR per night

Superhost

Chalet in Plymouth

4.72 out of 5 average rating, 185 reviews

5BR Chalet in Historic Town bet Killington & Okemo

5 bedroom secluded Chalet on a 5 acres of hilly forest land with a Hot tub (with a separate service fee). Located in Historical Plymouth Vermont between Killington & Okemo 20 min. in either direction (10 min. to Killington Skyship Gondola). 5 min. to Snowmobile tours, 9 min. to Long Trial Brewery, 2 min. to Plymouth Artesian Cheese factory & Calvin Coolidge Homestead Historic site. Also lots of lakes in the area with swimming, boating, and fishing. Canoe available at no cost (please inquire).

May 22 – 29

R2,588 ZAR per night

Superhost

Chalet in Stockbridge

4.85 out of 5 average rating, 115 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.

Oct 22 – 29

R2,946 ZAR per night

Guest favorite

Chalet in Killington

4.82 out of 5 average rating, 234 reviews

Killington Chalet - Hot Tub, Sauna, Boot Dryer

Our home is located on a quiet secluded road, just off Killington road, it's close to everything in Killington, the slopes, restaurants, bars & shops. It's the right side of a duplex with a large open living space that fosters great social interaction. We have 2-full-sized refrigerators, 24 PAIR SKI BOOT & GLOVE DRYER (Yes, dry gloves and boots every day), a private hot tub, sauna, wood stove, fire pit, 4 USB ports in every bedroom for charging, fresh linens & towels, a beautiful front yard

Feb 20 – 27

R15,721 ZAR per night

Guest favorite

Chalet in Killington

4.92 out of 5 average rating, 135 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!

Aug 2 – 9

R7,268 ZAR per night

Guest favorite

Chalet in Woodstock

4.98 out of 5 average rating, 95 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

Jan 7 – 14

R6,316 ZAR per night

Guest favorite

Chalet in Killington

4.99 out of 5 average rating, 90 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!!

May 28 – Jun 4

R4,970 ZAR per night

Guest favorite

Chalet in Killington

4.9 out of 5 average rating, 159 reviews

Close to Mountain and walk to restaurants!

Killington Mtn is 1.4 miles away, so the Sports Park is an easy drive. The area offers skiing, snowboarding, tubing, hiking, biking, kayaking, ATVing, PLUS two excellent golf courses nearby. Restaurants and shops are walking distance. The house is casual and comfortable, located on a quiet dirt road with nice views of the valley from the upstairs and deck. There is a HOT TUB and SAUNA and linens included. We also have full weeks available upon request at a substantial discount.

Jul 1 – 8

R4,361 ZAR per night

Guest favorite

Chalet in Killington

4.95 out of 5 average rating, 121 reviews

Treehouse Lodge in heart of Killington

Enjoy vacation in the Treehouse lodge with a true northeast mountain house experience. Located off the access road of one of Vermonts most active mountains, experience three seasons of prime New England fall foliage, Vermont's best snow trails, and summer events and hiking. This sleek, uniquely designed lodge offers a comfortable living room, spacious bedrooms, clean bathrooms, and fully stocked kitchen allowing guests to feel at home away from home.

May 15 – 22

R6,772 ZAR per night

Guest favorite

Chalet in Stockbridge

4.95 out of 5 average rating, 85 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.

May 22 – 29

R5,406 ZAR per night