Chalet holiday rentals in Windsor County

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!

15 Mins to Killington-Secret Speakeasy-Hot Tub

Luxury Ski Chalet in a GREAT location 🏂 5 MINUTES to PICO ⛷️ 15 MINUTES to KILLINGTON base 🛀🏼 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 💰 Cleaning Fee Reimbursement for stays >6 nights. Please see below! 🔋EV CHARGER 🛌 INCREDIBLY COMFORTABLE beds and linens 🐕 PET FRIENDLY 🚗 CONVENIENT YET REMOTE 🔥 SKI BOOT DRYER

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

BearVaria! Hot Tub, Deck, FirePit, Frisbee Golf

Welcome to Bear-varia! A Bavarian themed chalet in the heart of Killington. Close to everything with a great location off the access road by the market. Perfect for friends and families with plenty of space to spread out. Inside there's a fireplace, TV with Roku and fast internet. Also, an area for gaming with a second TV with Nintendo, a PacMan arcade game and plenty of board games to make memories and connect. Outside, there is a large yard and outdoor dining, fire pit and frisbee golf!

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!

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.

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!

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

Ledges Unit: Skyeship Gondola 2 miles 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.

The Overlook - Views | Hot Tub | Fire Pits | Games

Escape to stunning mountain views at The Overlook. Just 5 min from Killington Resort, restaurants, and shops. Enjoy the peacefulness of this private cozy mountain chalet after a long day of adventure and unwind in the hot tub, game room, or by the fireplace. Convenient Level 2 EV charger compatible with all EVs at the chalet. 🏔️ Mountain View 🌄 Large decks and balcony 🏖️ Hot tub ⚽️ Game room 🍗 Propane grill 🍳 Fully stocked kitchen 🪵 Fire pit 🔥 Fire table ⚡️Level 2 EV Charger

Hillcrest Manor of Vermont

40% weekly discount 60% monthly discount 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.

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.