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Chalet holiday rentals in Rutland County

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Top-rated chalet rentals in Rutland County

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

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Guest favourite
A private hot tub is illuminated with soft blue lights, creating a relaxing atmosphere. The hot tub features multiple jets and is surrounded by wooden walls and a partially covered area, ensuring privacy. Warm ambient lighting enhances the tranquil setting, inviting relaxation.
Chalet in Killington
4.84 out of 5 average rating, 252 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!

Top guest favourite
Chalet in Wells
4.9 out of 5 average rating, 152 reviews

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.

Top guest favourite
Chalet in Mendon
5 out of 5 average rating, 67 reviews

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

Superhost
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
4.9 out of 5 average rating, 189 reviews

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

Guest favourite
Chalet in Killington
4.99 out of 5 average rating, 100 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!

Guest favourite
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.
Chalet in Killington
4.96 out of 5 average rating, 113 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!

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.
Chalet in Killington
4.9 out of 5 average rating, 165 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 favourite
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
4.95 out of 5 average rating, 119 reviews

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.

Guest favourite
A cozy chalet is nestled among tall trees, with a fire pit surrounded by seating. The exterior showcases a mix of wood and green materials, and a balcony extends from the upper level. Sunlight filters through the leaves, creating a serene outdoor setting.
Chalet in Mendon
4.96 out of 5 average rating, 27 reviews

Pico/ Killington chalet, minutes to the mountain

Welcome to our boutique style mountain chalet nestled in tall birch trees. Our fully equipped modern home is 10 mins to Pico and 15 minutes to the Killington access road. Whether you’re in VT to shred the Beast of the East or leaf peep the Green Mountains our home offers a cozy retreat for some time to relax between adventures. Close to breweries, orchards, hiking on the Appalachian Trail/Long Trail, and the convenience of Rutland. AND… We’re walking distance to pancakes and putt-putt =).

Top guest favourite
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
4.98 out of 5 average rating, 107 reviews

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, 45 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!

Guest favourite
Chalet in Killington
4.98 out of 5 average rating, 85 reviews

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

Popular amenities for chalet rentals in Rutland County

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

Family-friendly chalet rentals

A modern kitchen showcases white cabinetry and stainless steel appliances, including a microwave and oven. A spacious island with a marble countertop offers extra prep space. Natural light pours in through the windows, illuminating the clean lines and neutral tones of the room.
Chalet in Killington
4.8 out of 5 average rating, 5 reviews

Newly Renovated Killington Chalet

A cozy chalet is nestled in a snowy landscape, surrounded by tall trees. The building features a sloped roof covered in snow and a front deck with white railings, providing a welcoming entrance. A flat driveway leads up to the entrance, enhancing accessibility.
Chalet in Plymouth
4.8 out of 5 average rating, 41 reviews

Chalet Schlosser

The exterior of the house showcases a modern design with gray siding and a red metal roof. A spacious wooden deck wraps around the front, providing ample outdoor seating space. Tall windows allow for natural light, and natural surroundings create a picturesque backdrop.
Chalet in Pittsfield
4.95 out of 5 average rating, 56 reviews

Luxury Heart of VT Green Mountains

Guest favourite
A snow-covered exterior of a two-story chalet is visible, featuring warm-toned wood siding and a spacious deck. Multiple windows allow natural light, while the surrounding snowy landscape creates a serene atmosphere. The entrance is indicated by a covered area leading to the interior.
Chalet in Mendon
5 out of 5 average rating, 26 reviews

Cozy Vermont Getaway minutes from Killington Mt.

A cozy dining area features a custom-made wooden table surrounded by built-in seating. The table is set with placemats and is positioned under warm lighting, enhancing the inviting space. A framed artwork of a tree hangs on the wall, adding a decorative touch.
Chalet in Ludlow
4.81 out of 5 average rating, 16 reviews

A-Frame Chalet Getaway on Okemo Mountain

A charming chalet-style house is nestled among tall trees, showcasing a spacious deck with multiple large windows. A hammock hangs between trees, and a decorative flag adds a festive touch to the outdoor area. The lush green lawn slopes gently down to the water.
Chalet in Castleton
4.67 out of 5 average rating, 27 reviews

Eckley Point Lake House

The chalet exterior is illuminated at night, showcasing a modern design with large windows. Snow blankets the pathway leading to the entrance, highlighting the warmth of the interior lights. Decorative snowflakes are displayed in the windows, adding a festive touch.
Chalet in Pittsfield Killington
4.67 out of 5 average rating, 12 reviews

Killington Mid-Century - Ski Chalet

A spacious living area features large windows, allowing natural light to fill the space. A dark leather sofa is positioned on warm wooden flooring, complemented by a soft, draped blanket. The open layout leads towards a partially visible kitchen area in the background.
Chalet in Plymouth
4.83 out of 5 average rating, 29 reviews

Hawk House

Luxury chalet rentals

Guest favourite
Chalet in Killington
4.97 out of 5 average rating, 38 reviews

Large family ski home 5bd fireplace chefs kitchen

Guest favourite
A three-level chalet is shown, featuring a wooden exterior and a spacious front deck with chairs. Large windows provide natural light, while surrounding trees create a natural backdrop. A gravel path leads to the entrance, and a grassy area is visible in the foreground.
Chalet in Plymouth
4.96 out of 5 average rating, 74 reviews

OZ- 6BR Ski Chalet Between Killington & Okemo

Superhost
A spacious chalet-style home is set against a backdrop of autumn foliage. Large windows catch natural light, emphasizing the architectural features. The gray exterior is complemented by stone accents, and a gravel driveway leads up to the entrance, surrounded by trees.
Chalet in Killington
4.83 out of 5 average rating, 77 reviews

West Park Chalet at Killington: Great For Groups!

Superhost
A spacious green ski house is shown, featuring large windows and a steeply pitched roof. The wrap-around deck, surrounded by snow-covered ground and tall trees, provides outdoor space for relaxation. The house integrates with its natural surroundings, showcasing a cozy mountain retreat.
Chalet in Mount Holly
4.93 out of 5 average rating, 67 reviews

Okemo Hot Tub Fireplace Billiard

Top guest favourite
Chalet in Killington
4.98 out of 5 average rating, 82 reviews

Vintage 70s A frame - Big Hot Tub - 7 min from K1

Guest favourite
A living area is showcased with a fieldstone fireplace surrounded by large greenhouse windows, allowing natural light to flood the space. Two cozy leather chairs and a wooden coffee table are positioned on a colorful area rug, creating a warm and inviting environment.
Chalet in Plymouth
4.97 out of 5 average rating, 33 reviews

Spacious chalet, perfect for 2 families

Superhost
The spacious living area features high post and beam ceilings adorned with natural wood accents. A stone fireplace serves as a focal point, while comfortable seating arrangements invite relaxation. Large windows allow natural light to brighten the space, and a staircase leads to a lofted area.
Chalet in Killington
5 out of 5 average rating, 5 reviews

Viewmont Chalet - Beautiful post and beam house wi

Top guest favourite
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.
Chalet in Killington
5 out of 5 average rating, 40 reviews

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

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