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Chalet vacation rentals in Rutland County

Find and book unique chalets on Airbnb

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Popular amenities for Rutland County chalet rentals

Family-friendly chalet rentals

Guest favorite
A secluded chalet is surrounded by snow-covered trees, showcasing its wrap-around deck. The winter landscape features undisturbed snow blanketing the ground, while blue skies peek through scattered clouds above.
Chalet in Plymouth
4.75 out of 5 average rating, 215 reviews

5BR Chalet in Historic Town bet Killington & Okemo

PamalaRating, 5 stars2 months ago
We had an issue with our previous rental and needed to find a place to stay that is pet friendly and available. Rad and Carol responded quickly to our reservation request. The house was made available to us early in the day and hot tub prepped last minute for us to enjoy! The Chalet is beautiful and spacious, the location is private and relaxing. The wood stove kept us warm and cozy while we enjoyed watching light snow fall. We would definitely stay there again and bring our family with us!
Guest favorite
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

EmmaRating, 5 stars3 months ago
Wonderful stay - perfect location
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 stars2 months ago
Great place to stay for okemo mountain!! Very close to local restaurants and the mountain
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

AbbyRating, 5 stars5 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.
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 stars8 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 stars3 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 otherā€˜s company. It was the perfect spot for a ski getaway. We all agreed we would love to stay there again.
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
4.65 out of 5 average rating, 26 reviews

Eckley Point Lake House

JRating, 5 stars20 months ago
La maison correspondait au descriptif, endroit très calme au bord du lac, équipement complet, jeux, kayak à disposition, nous avons passé un agréable moment en famille. Merci Georgina de nous permis de partir plus tard. Bon souvenir!
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 stars3 months 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 stars3 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.
An open-concept living area features a modern wood-burning stove and large skylights, allowing natural light to fill the space. A dining table sits in the foreground, with a minimalist kitchen area visible through the glass doors, enhancing the airy feel of the chalet.
Chalet in Stockbridge
4.95 out of 5 average rating, 38 reviews

Private Mountain Sanctuary | 15 Min to Killington

CoreyRating, 5 stars1 week ago
One of the best locations in the northeast, period. The 360 degree mountain top view is unmatched. The home is beautiful and well connected via solar and starlink, so while we could unplug, it was also possible to reply to emails and get some work done. 11/10
Top guest favorite
A high chair with two levels is positioned in a cozy nursery. A soft, plush toy resembling a leopard sits on the top shelf. In the background, a wooden crib is visible, featuring a patterned mattress. Warm, natural light filters into the room.
Chalet in Killington
4.97 out of 5 average rating, 35 reviews

Classic Ski Chalet+ wood fireplace+chef’s kitchen

JillRating, 5 stars2 weeks ago
Second time staying here. Such a beautiful quaint and private location. The house is charming and has every amenity we needed for a long weekend. away. Leslie is a wonderful responsive host who is always very accommodating! Highly recommend 😊
Guest favorite
A broad view showcases a gently rolling mountain, highlighted by soft golden sunlight. Lush greenery and sparse trees are visible in the foreground, framing the landscape under a clear blue sky. The scene captures the tranquility of nature, inviting leisurely exploration.
Chalet in Mendon
5 out of 5 average rating, 26 reviews

Cozy Vermont Getaway minutes from Killington Mt.

StanleyRating, 5 stars4 months ago
Plenty of space for a ski trip for 12 people, would stay again!
The chalet's exterior showcases a large A-frame structure with expansive windows. Surrounded by vibrant autumn foliage, the natural wood finish complements the rustic design. A spacious outdoor deck is visible, enhancing the connection to the surrounding landscape.
Chalet in Killington
5 out of 5 average rating, 22 reviews

Killington Ski Chalet on Great Eastern Trail

SherryRating, 5 stars17 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!
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 stars3 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!
Top guest favorite
A bright sleeping area features a spacious bed with neutral bedding and two accent pillows. Large windows allow natural light to fill the room, showcasing views of surrounding trees. A modern aqua chair is positioned near the window, complementing the room's wooden beams and ceiling.
Chalet in Killington
4.98 out of 5 average rating, 80 reviews

Chateau Charmaine - Big Hot Tub - No Cleaning Fee

WillRating, 5 stars2 weeks ago
Of all the places I've stayed, this is the best one by far. This house is very unique, spacious and relaxing and exceeded all of our expectations. This house has a record player with cool records. Does anything more need to be said after that?!? Well, yes! There is a fire ring behind the house, the house is in a very peaceful setting and the hot tub is amazing, the furniture and beds are clean and comfortable, the kitchen had everything you could possibly ever want and . . . this is the most cozy house ever, with individual thermostats for each room and each bathroom too, plus a nice and blazing pellet stove in the living room which is super easy to use. Whoever designed and built this place was a true master of space. And the hosts were the most responsive and kind - hats off to hosts Jared & Corey for such a great place! We will be back someday.
Top guest favorite
Chalet in Killington
5 out of 5 average rating, 71 reviews

BearHaus Central AC, HUGE Hot Tub, Awesome FirePit

JenniferRating, 5 stars4 weeks ago
I’ve stayed at this home multiple times, and it’s always a pleasure. The neighborhood is quiet and peaceful, making it a perfect place to relax. The host is incredibly welcoming and makes the entire process smooth and stress-free. The house is always clean, well-maintained, and stocked with everything I need. I always look forward to staying here and would highly recommend it to anyone looking for a comfortable and reliable Airbnb.

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