Chalet vacation rentals in Rutland County

A spacious living area features vaulted wooden ceilings with exposed beams, allowing natural light to fill the room. Comfortable couches are arranged around a central coffee table, with a large television set against the wall. Light-colored curtains frame the windows, enhancing the inviting ambiance.

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!

4.9 out of 5 average rating, 148 reviews

A custom-built chalet is nestled among lush greenery, showcasing a unique A-frame design. The exterior features stone columns and wooden balcony railings. An American flag can be seen hanging, adding a touch of character to the inviting setting.

Chalet in Wells

Views! Entire Chalet, FAST Wi-Fi, All 18 Acres

Base rate includes six guests. We welcome events reunions, weddings. Scenic view, nearby lake, golf, hiking! Your private Authentic Chalet is 3600 sq ft on 18 acres. Sleeps 13 (3 bedrooms and full bathrooms, 1 King, 2 Queen, 3 Twin, 2 Queen sleeper-sofas). Summer HVAC, Artisan fireplace, oven, Induction cooktop, air fryer stocked kitchen, ROKU HDTV, fast Wi-Fi, FirePit Patio. Linens/bath towels, soaps-supplied. Optional: A private separate 350 sq ft studio/office. 5-star by work-from-homers.

4.93 out of 5 average rating, 187 reviews

The exterior of the upper unit duplex is surrounded by snow, showcasing a wooden deck with a railing and steps leading to the entrance. A prominent stone chimney rises from the roof, and large windows provide a view of the surrounding forest.

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

A well-lit living room features a spacious sectional sofa facing a fieldstone fireplace. A wooden coffee table sits centrally, and a Samsung flat-screen TV is mounted above the fireplace. Large windows provide natural light and views of the surrounding greenery, enhancing the serene setting.

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, 64 reviews

An aerial view captures the chalet nestled among lush greenery, with mountains rising gently in the background. The warm hues of sunset fill the sky, while string lights illuminate the exterior, creating an inviting atmosphere amidst the natural landscape.

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

A spacious wooden deck is featured, equipped with a large patio table and six chairs. A hot tub is positioned nearby, surrounded by trees. Large sliding doors offer access to the interior, allowing natural light to fill the space.

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!

The entrance of the home is warmly adorned with string lights, creating a welcoming glow. A sturdy wooden front door is flanked by large glass windows, while a sloped pathway leads up to the entryway. Stone steps provide access to the porch, surrounded by natural foliage.

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

A two-story chalet features a striking facade with dark wood framing and cream-colored walls. Snow covers the roof and ground, enhancing the winter ambiance. Yellow window shutters and stacked firewood are visible in front, providing a cozy, rustic touch to the scenic setting.

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.

A spacious living area features a large, grey sectional sofa accompanied by a wooden coffee table. Natural light streams in through the windows, and the warm wooden floors create a cozy environment. The open layout leads seamlessly to a fully equipped kitchen in the background.

5 out of 5 average rating, 30 reviews

5 min Ski Bike Golf| Nightlife| Hot Tub| Arcade

Nestled in the heart of Killington, our 4 BR/2 BA cozy retreat for anyone seeking a peaceful getaway! Gourmet kitchen, perfect for preparing meals together. Open-concept living w/ ample room for quality time. Bedrooms thoughtfully designed to ensure a restful night and flexible sleeping arrangements. Unwind after a day on the mountains with our rain showers & heated floors or outdoors in our relaxing Hot Tub oasis. Dry your gear with our heated gear dryer. Make memories and book today!

4.98 out of 5 average rating, 103 reviews

The chalet is set against a backdrop of mountains and trees. The property features a large green lawn, and two dogs are seen resting on the grass in the foreground. The warm exterior of the home, complete with a deck, can be seen in the background.

Chalet in Wells

Chalet on a Hill w/ Mountain & Lake View, Hot Tub

A beautiful chalet situated between mountains and Lake St Catherine. Whether on the deck or inside the house, you can enjoy the tranquil and serene view of the mountains and the lakes. At over 3000 sq ft, the house offers multiple gathering areas, including separate living room(s), a sociable kitchen, a pool table, and a bar. A perfect home for a retreat. Located less than 10 mins from Lake St Catherine Park and country club and many hiking and mt-biking options for the active guests.

Superhost

An aerial view captures the modern chalet nestled amidst vibrant autumn foliage. The surrounding landscape reveals rolling hills and expansive mountain views under a soft, cloudy sky, highlighting the property's secluded location.

Chalet in Stockbridge

4.93 out of 5 average rating, 44 reviews

Private Mountain Sanctuary | 15 Min to Killington

*Winter Stays* Must have 4WD vehicle with snow tires or snow chains. We want you to make it safely up the mountain for those breathtaking views! This is not just a house. Welcome to your one-of-a-kind off-grid nature adventure! Wow: - Designer modern chalet on 150+ private acres - Off-grid privacy, while 15 minutes to Killington. 5 min to world class mountain bike trails. - 360 degree panoramic view - VAST trail, walking trails - Hike, Bike, Ski, Snowshoe, Stargaze, Views Views Views!