Chalet holiday rentals in Windsor County

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!

4.93 out of 5 average rating, 187 reviews

Chalet in Stockbridge

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

4.96 out of 5 average rating, 110 reviews

Prime Killington Proximity | Ski, Sauna, & Soak!

Awarded Airbnb’s "Most Loved Homes!" Escape to our warm chalet, just 5 minutes from the slopes in Killington's most desirable neighborhood. Ski, hike, bike, or golf by day–then unwind in our private sauna, soak in the outdoor hot tub, or curl up by the wood-burning fireplace in front of the TV. Comfy beds, full kitchen, fast WiFi, and billiards & darts in the game room. Close to great restaurants, breweries, nightlife, golf, and breathtaking fall foliage. Your perfect mountain getaway awaits!

5 out of 5 average rating, 65 reviews

Chalet in Mendon

Luxury-Secret Speakeasy-Hot Tub-Killington Area

Luxury Ski Chalet in a GREAT location 🏂 5 MINUTES to PICO ⛷️ 15 MINUTES to the K1 OR SKYSHIP GONDOLAS in KILLINGTON ❄️ 10 MINUTES to the action in KILLINGTON 🛀🏼 BRAND NEW HOT TUB and SOAK SHACK 🥃 SECRET BOOKCASE DOOR Hiding a large, well-equipped SPEAKEASY 🌲 Massive themed KIDS ROOM 🌱 2 MASTER BEDROOMS 🎱 THOUGHTFUL AMENITIES for large families seeking luxury and fun 🔋EV CHARGER 🛌 INCREDIBLY COMFORTABLE beds and linens 🚗 CONVENIENT YET REMOTE 🔥 SKI BOOT DRYER 🫧 Laundry

Superhost

Chalet in Stockbridge

4.84 out of 5 average rating, 169 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

4.9 out of 5 average rating, 164 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!

4.98 out of 5 average rating, 109 reviews

Chalet in Woodstock

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

5 out of 5 average rating, 129 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

4.95 out of 5 average rating, 118 reviews

Chalet in Plymouth

Ski, mountain bike, leaf peep. Let’s go!

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.

4.91 out of 5 average rating, 536 reviews

Chalet in Fairlee

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.

4.97 out of 5 average rating, 88 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!