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Chalet vacation rentals in Rutland County

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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
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

TimRating, 5 stars24 months ago
Guys weekend went smooth with no real hiccups. View and boat lift were great! Hopefully booking again next spring! šŸŽ£ā›³ļøšŸ˜Ž
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!
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 stars9 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.

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.
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 😊
An indoor hot tub is set in a spacious room, surrounded by large windows offering views of the outdoors. The tub is filled with water, and three individuals are enjoying a relaxing soak, creating a serene atmosphere.
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.
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!
Guest favorite
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, 26 reviews

Pico/ Killington chalet, minutes to the mountain

MelissaRating, 5 stars4 months ago
The home was the perfect getaway for a weekend of snowboarding. Enough space for everyone to have their own area but also cozy enough to be all together, perfect mix of both. Absolutely would recommend to anyone looking to be close to the mountain and all the other amenities the Killington/Pico area has to offer.
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 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.
Guest favorite
An open kitchen and dining area is highlighted by a high, wooden ceiling. The kitchen features rich cabinetry and modern appliances. A round pendant light hangs above a large dining table with orange chairs, complemented by additional seating along the wall. Large windows provide natural light and views of the outdoors.
Chalet in Pittsfield
4.86 out of 5 average rating, 37 reviews

The Sklarzhaus

StevenRating, 5 stars3 months ago
We really enjoyed staying at Fiona’s place for our ski trip to Killington. The house was warm and inviting when we arrived. The beds were comfortable and clean. The kitchen and living room gave us plenty of space for us to stretch out.

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