Chalet vacation rentals in Rutland County

Find and book unique chalets on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Rutland County chalet rentals

Family-friendly chalet rentals

Superhost
The exterior of Hideaway Chalet is covered in a thick layer of snow, surrounded by tall trees. The structure features two levels with wooden balconies. In the foreground, a hot tub is visible, partially buried in snow, emphasizing the winter setting.
Chalet in Killington
4.73 out of 5 average rating, 11 reviews

Luxury of large space by ski slopes, deck HOT TUB

SandaRating, 5 stars49 months ago
Our stay at Hideaway was relaxing and exactly how we expected it. The cabin is within a short driving distance from the ski areas and grocery stores, and very comfortable for a family with two children. The host was easy to reach and responded quickly to communication. Overall, a wonderful vacation.
Top guest favorite
Chalet in Pittsfield
5 out of 5 average rating, 54 reviews

Mountain Bliss: Spacious Retreat Near Killington

WilliamRating, 5 stars1 month ago
This place is a lovely spot that exceeded expectations for me and my friends! The host was super communicative throughout the whole process, from right after booking through checkout. It’s an amazing place and I would definitely stay here again.
Guest favorite
A rustic ski chalet is nestled among snow-covered trees, with a sloping driveway leading to the entrance. The building showcases a wooden deck and vibrant blue exterior, surrounded by a serene winter landscape.
Chalet in Ludlow
4.82 out of 5 average rating, 76 reviews

Mountain Chalet + HOT TUB

ChristopherRating, 5 stars1 month ago
Great place to stay for okemo mountain!! Very close to local restaurants and the mountain
Superhost
The exterior of a large chalet is showcased, featuring a steeply pitched roof and expansive windows. A wraparound deck provides access to the outdoors, surrounded by lush greenery. The structure exhibits a dark wood finish that contrasts with the clear blue sky.
Chalet in Granville
4.81 out of 5 average rating, 89 reviews

Hilltop Chalet on 20 rolling acres

PaulRating, 5 stars6 months ago
My wife and I thoroughly enjoyed our stay at John's Chalet. The house was exactly as described beautiful inside and out. We loved seeing all the wildlife around the home every day. The home is very private and close to many outdoor activities especially hiking. We would certainly consider this home again on our next trip to Vermont. Sincerely Paul & Rebecca
A brown chalet-style home is situated among lush green trees, presenting a welcoming entrance with a red deck and steps. The front door is framed by two large windows, and a small potted plant adds a touch of color near the entrance.
Chalet in Ludlow
4.76 out of 5 average rating, 128 reviews

Charming Lakefront House

EricaRating, 5 stars2 months ago
This home was just what we were looking for. It is charming and spacious, rustic in all of the right ways, with a gorgeous view of the lake, and so close to Okemo. The master bedroom was huge, and we really enjoyed the large communal space with the wood-burning stove. Some of us were cooking while others were playing games, while others were relaxing by the fire, so that we could all easily enjoy each other‘s company. It was the perfect spot for a ski getaway. We all agreed we would love to stay there again.
A rustic A-frame chalet is showcased, featuring large glass windows that allow natural light to fill the interior. The exterior is constructed of natural wood, complementing the snowy landscape. A front deck is visible, extending from the main entrance, while stairs lead down to the snowy ground.
Chalet in Killington
5 out of 5 average rating, 22 reviews

Killington Ski Chalet on Great Eastern Trail

SherryRating, 5 stars15 months ago
This house is amazing! Our family Killington trip was enhanced by staying at this beautiful chalet. The pictures online do not do this property justice as it is much more beautiful in person! The kitchen is very well stocked with everything you need, the house was clean and immaculate with enough linens for everyone. Virginia was responsive to any questions and very welcoming. We had a snowstorm, and the plow came promptly to plow the driveway. There is an echo from the loft in the main floor, and it is much quieter on the lower level. There was ample wood for the fireplace. We would love to come again next year!
Guest favorite
A spacious lawn area is visible in front of the chalet, featuring lounge chairs arranged along the grassy expanse. The chalet's deck overlooks the yard, with steps leading down from the outdoor seating area. Surrounding trees provide a natural backdrop.
Chalet in Hubbardton
4.94 out of 5 average rating, 96 reviews

Chalet on Pristine Beebe Lake

ConnieRating, 5 stars7 months ago
This property was the most peaceful stay I have ever had. So quiet and relaxing. It was the perfect getaway while we were in town for a wedding. The stay had everything we needed to make dinners for the family and a wonderful porch overlooking Lake Beebe. Thanks for sharing your space with my family and me. Side note: Dylan was very successful fishing in this lake and the boats made it easy to explore the lake.
Guest favorite
A serene ranch-style home is nestled amid a snowy landscape, featuring a combination of dark and light wood siding. The roof is dusted with snow, and the front porch is furnished with rocking chairs. Surrounding trees create a peaceful, wintry setting.
Chalet in Mount Holly
4.92 out of 5 average rating, 60 reviews

3 bedroom mountain getaway

DefneRating, 5 stars1 month ago
My friends and I had a great stay at Daniel’s place! It was very clean with plenty of space to accommodate all of us. We were skiing at Okemo, which was a quick 15 minute drive. Would definitely recommend staying here!

Luxury chalet rentals

The chalet is displayed amid a snowy landscape, showcasing a sloped roof covered in white snow. A wooden balcony with a railing is visible, along with a stairway leading to the entrance. Snow drifts surround the property, surrounded by trees in a winter setting.
Chalet in Plymouth
4.8 out of 5 average rating, 41 reviews

Chalet Schlosser

JeremyRating, 5 stars2 months ago
Chalet Schlosser was perfect for our short vacation week excursion. Plenty of beds for a couple families, super cozy, and everything worked as advertised, including the fireplace which kept us warm and helped dry our gear. Really convenient to Killington lodges, easy drive to town, driveway was plowed and cleaned during a storm while we were there without needing to ask about it. The "chalet" was the cherry on top of a great weekend.
Top guest favorite
A spacious living area is characterized by high wooden ceilings and exposed beams. A stone fireplace serves as a focal point, with comfortable seating arranged around it. Natural light filters in through large windows, illuminating the wood-paneled walls.
Chalet in Killington
4.97 out of 5 average rating, 34 reviews

Classic Ski Chalet+ wood fireplace+chef’s kitchen

ChristopherRating, 5 stars1 month ago
We had a great weekend here. It was comfortable with the 8 of us in this house. It was cozy with the fireplace, we utilized the grill and the ping pong table. The location was great for our skiing weekend! Very close to Killington and Pico.
The exterior of the house is nestled among trees, showcasing a rustic design with a red metal roof. A wraparound porch features wooden supports, and the driveway leads to a garage beneath the porch. Natural landscaping complements the serene mountain surroundings.
Chalet in Pittsfield
4.95 out of 5 average rating, 56 reviews

Luxury Heart of VT Green Mountains

AbbyRating, 5 stars3 months ago
Fantastic place for a ski trip to Killington. Large and comfortable with plenty of room for 3 adults and 3 teens. We enjoyed the fireplace and hot tub. Communication was great. It was an easy drive to Killington. One of the best places we’ve stayed. We’d definitely stay there again.
Guest favorite
A wooden deck features two cushioned seating chairs and decorative pillows. Surrounding trees provide a natural backdrop, with leaves scattered on the ground. The setting conveys a peaceful outdoor space, ideal for enjoying tranquil moments in nature.
Chalet in Mendon
5 out of 5 average rating, 26 reviews

Cozy Vermont Getaway minutes from Killington Mt.

StanleyRating, 5 stars3 months ago
Plenty of space for a ski trip for 12 people, would stay again!
Guest favorite
Chalet in Killington
4.87 out of 5 average rating, 67 reviews

Secluded 4BR cabin w/ HOT TUB- Walk to Access Rd!

CarolineRating, 5 stars1 month ago
Place was great, couple of minute drive to the mountain, nightlife was right around the corner and the accommodation had a ton of space.
A bright dining area is depicted with a round table surrounded by yellow chairs. Natural light enters through multiple windows, highlighting the wooden beams and rustic decor. A spiral staircase leads to an upper level, and a red door adds a pop of color to the inviting space.
Chalet in Ludlow
4.85 out of 5 average rating, 82 reviews

Okemo Mountain-Newly Renovated w AC, hottub, WiFi

KarenRating, 5 stars2 months ago
Brent’s house was beautiful and exactly as pictured. We loved the decor and it matched the mountain house feel. It was perfect for our family of 5 and we loved the board games in the living room. Very easy access to okemo to ski and to town. Recommend 4 wheel drive if you are coming in the winter as the roads and drive away could be a challenge without that! We hope to visit again next year!
Top guest favorite
Chalet in Killington
4.99 out of 5 average rating, 69 reviews

The Overlook - AC | Hot Tub | Fire Pit | Games

AndrewRating, 5 stars1 month ago
Beautiful home right down the street from Killington. The views are what makes this place special... The house is equipped with more than what's needed. There are so many towels and throw blankets. If this house is available, you won't regret it!
Top guest favorite
A wooden deck is featured, showcasing a pair of woven chairs and a small table. The natural surroundings are visible through large windows and greenery creates a serene backdrop. The structure exudes a rustic charm, inviting relaxation in the fresh air.
Chalet in Stockbridge
4.94 out of 5 average rating, 48 reviews

BENT TREE Vermont, Mtn Chalet 25 min to Killington

PaulRating, 5 stars2 months ago
Beautiful location and very easy access to Killington Ski Resort! We had >1 foot of snow and the steep driveway was plowed well before departure. Very clear communication and instructions made for a very relaxing time. Thank you for sharing your home!

Destinations to explore

  1. Airbnb
  2. United States
  3. Vermont
  4. Rutland County
  5. Chalet rentals