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Chalet vacation rentals in Windsor County

Find and book unique chalets on Airbnb

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Popular amenities for Windsor County chalet rentals

Family-friendly chalet rentals

Superhost
An aerial view of the living area and dining space showcases an open layout. A black dining table, surrounded by red chairs, sits against a wall. Adjacent, a sectional sofa with neutral tones faces a coffee table, with light streaming through large windows.
Chalet in Plymouth
4.75 out of 5 average rating, 215 reviews

5BR Chalet in Historic Town bet Killington & Okemo

PamalaRating, 5 stars4 weeks 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!
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.
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
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!
The exterior of the house features a wooden façade and large windows, set against a bright blue sky. A spacious deck with a railing is visible in front, surrounded by snow-covered ground and sliding stairs leading to the entrance.
Chalet in Peru
4.84 out of 5 average rating, 44 reviews

Vermont Mt. House, near Bromley and Hapgood Beach

EdwardRating, 5 stars3 months ago
Great location. Beautiful views. Host was extremely responsive. Great fire place and living room.
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!
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

BenRating, 5 stars39 months ago
Great cabin - very spacious and close to the hill. Amenities (pool table, hot tub) were also nice.

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.
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.
Top guest favorite
An outdoor deck showcases a fire table with vibrant flames, surrounded by a dining set and scenic mountain views. Wooden seating areas provide a relaxing space, while the lush greenery and autumn foliage enhance the tranquil setting.
Chalet in Killington
4.99 out of 5 average rating, 69 reviews

Overlook | AC | Hot Tub | Fire Pit | Views | 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!
Top guest favorite
Chalet in Killington
5 out of 5 average rating, 69 reviews

BearHaus- Central AC, HUGE Hot Tub, FirePit

WhitneyRating, 5 stars3 weeks ago
Very family friendly ski rental. Thank you!
Superhost
A hot tub is situated on a wooden deck, featuring steps for easy access. It is surrounded by a verdant forest, providing a natural setting for relaxation. The cover is partially opened, revealing the bubbling water inside.
Chalet in Mount Holly
4.91 out of 5 average rating, 32 reviews

Cozy Chalet near Okemo Jacuzzi/Sauna

KellyRating, 5 stars2 months ago
My family and I had a great week at Gabriella's place in Mt. Holly. It is a 5 min drive from Jackson Gore Base at Okemo, which made for very easy skiing (and parking!). Gabriella was responsive and friendly when we checked in. We happened to be there during a snowstorm and the drive was plowed by midmorning the next day. It was also very cold, and despite the somewhat quirky heating, we were able to stay warm while at the house. My husband and daughter enjoyed the foosball in the basement (not heated, but does have plug in heater). Hot tub was great. Only thing guests might want to note is that there are limited pots and cooking supplies so it was challenging to make meals. Also, the dishes provided are melamine/not microwave safe so we bought paper plates for when we wanted to reheat food. The home is, however, well stocked with glasses, coffee cups, baking dishes, and pans. Beds were comfy. Heated mats on front steps were very helpful. All in all, a great stay and would rent again!
Guest favorite
A sunlit entryway features a combination of windows and a door, providing views of the outside. Comfortable seating is available with multiple cushioned chairs arranged around a glass-top table. Wooden accents and a rustic ceiling enhance the inviting atmosphere of this space.
Chalet in Killington
5 out of 5 average rating, 19 reviews

5 min Ski| 1 min Nightlife| Hot Tub| Arcade| Fires

MitchellRating, 5 stars1 week ago
Awesome place and location! Andrew was very responsive and the house was very clean. Just a quick shuttle ride to the downtown area and only minutes from the mountain. I will definitely be staying again

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