Some info has been automatically translated. Show original language

Chalet vacation rentals in Berkshire County

Find and book unique chalets on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Berkshire County chalet rentals

Family-friendly chalet rentals

Guest favorite
A spacious great room features high ceilings with wooden beams and large triangular windows. A wooden dining table is situated near the windows, while comfortable seating arrangements with neutral-toned upholstery are arranged around a central fireplace. Natural light fills the space, enhancing the open concept design.
Chalet in Richmond
4.97 out of 5 average rating, 93 reviews

Updated Berkshires Chalet Mins to Tanglewood/Lenox

GlennRating, 5 stars9 months ago
This was our 2nd stay at this property. If you love the Berkshires and all the activities available, this house and property are perfect. It is very well maintained and the great room is perfect for our large family. Nothing like the hot tub and sitting around a fire after a busy day of hiking and Tanglewood. Wendy is an excellent host, never a problem.
Top guest favorite
A chalet-style home is situated on a forested property, with a spacious deck extending from the front. Large windows reflect the surrounding greenery, showcasing a modern aesthetic against a backdrop of autumn foliage. Rock formations and scattered leaves cover the ground.
Chalet in Peru
4.92 out of 5 average rating, 287 reviews

Swiss Chalet Style Timberframe Home in Berkshires

WilliamRating, 5 stars1 month ago
I had a wonderful stay at Laura’s place. The home is not only beautiful but thoughtfully constructed. Its exposed wood frame feels so natural and adds to the calming atmosphere. The backyard was clean, maintained, and offered a serene space to relax. Laura’s instructions were clear and made finding and settling into the house easy. The bedrooms and bathrooms were incredibly cozy and well-kept. Every detail made the space feel warm and welcoming. It’s also a fantastic spot for groups. Our group of six friends fit very comfortably, with plenty of space to relax and unwind. I’d absolutely recommend this home to anyone looking for a peaceful, comfortable getaway.
Guest favorite
A modern kitchen is presented with sleek, dark cabinetry and stainless steel appliances. A large window provides natural light, while a geometric light fixture hangs overhead. The open design features a view into the living space, showcasing a blend of stone and wood elements.
Chalet in New Marlborough
4.92 out of 5 average rating, 53 reviews

Modern Secluded Ski Chalet | 40 Acres | Family

JustinRating, 5 stars9 months ago
Absolutely amazing stay! I have never stayed with such hospitable and genuinely nice hosts. In addition their home was filled with interesting gadgets and beautiful aesthetic, they’ve inspired to replace every toilet in my house! I hope I have the pleasure of staying here again! Thank you Jennifer and Evan!
A patio area overlooks the serene lake, featuring lounge chairs with striped cushions and a wooden dining table. A striped umbrella provides shade, while lush greenery and calm waters are visible in the background, enhancing the outdoor setting.
Chalet in Lee
4.83 out of 5 average rating, 65 reviews

Waterfront lakehouse in Berkshires

LorriRating, 5 stars9 months ago
The chalet was perfect for our relaxing 5 day vacation. We enjoyed swimming off the dock and taking the kayaks out on the lake. The space is wonderful and the view is amazing! We found it hard to get motivated to go out to dinner and lunch because we didn't want to miss one second of the wonderful view!
A cozy cottage is nestled among lush greenery, featuring a wooden exterior with large windows. A balcony extends from the upper floor, furnished with several chairs. The surrounding landscape includes tall trees and a vibrant mix of plants, creating a serene natural environment.
Chalet in Stephentown
5 out of 5 average rating, 13 reviews

Ski Cottage in the Berkshire hills

WendyRating, 5 stars34 months ago
A rustic, charming, and treehouse-like stay in the Berkshires. The house is not modern by any means but has a wonderful, well-loved, and lived-in feel. Elissa was an incredible host and very responsive. We really enjoyed exploring Jiminy peak, Cherry Plain State Park, rowing and swimming in the pond, exploring the Farmer's market in Troy, kayaking along the Hudson near Albany, and hiking to Kinderhook creek. Our family also enjoyed berry picking at Berry Patch Farms (and getting their CSA). I'm sure the trees here would be incredible in the fall. We were lucky enough to catch the Perseid meteor shower, Saturn, Jupiter, and the super moon while we were here. The Wifi was good enough for zoom calls but definitely would cut out whenever we used the microwave. All-in-all a lovely getaway and very close to hiking trails.
A spacious living area features large windows revealing a serene forest view. A circular coffee table, surrounded by curved sofas, centers around a unique fireplace. Natural wood elements complement the light-colored walls and flooring, creating a calming atmosphere.
Chalet in Canaan
4.56 out of 5 average rating, 68 reviews

R3Bliss - Estate with Hot Tub, Tennis Court & Pool

RobinRating, 5 stars4 months ago
Great stay. Bathrooms r small and outdated but the fireplace and hot tub and property outweigh the cons.
Guest favorite
A striking octagonal home is illuminated at dusk, showcasing wrap-around glass windows that blend with the surrounding woodland. The exterior features natural stone accents, and a warm glow from a light at the entrance creates a welcoming ambiance amidst a snowy landscape.
Chalet in Otis
4.94 out of 5 average rating, 418 reviews

Mid-Century Glass Octagon in the Berkshires

ChelseaRating, 5 stars3 weeks ago
If you’re looking for a secluded area away from all the noise, this is the place! Katherine’s home was very peaceful and quiet. It was clean and I have no complaints at all. The WiFi was fast and my favorite part about this place is the projector. A great spot to watch movies! Katherine was a very responsive host and we felt right at home. I definitely recommend booking!
Top guest favorite
A cozy living room features two light-colored sofas adorned with decorative pillows. A wooden coffee table sits at the center, complemented by a woven area rug. A tall bookshelf filled with baskets is visible in the background, alongside a small side table and wall art.
Chalet in Monterey
4.98 out of 5 average rating, 84 reviews

Cozy French Country chalet

JacobRating, 5 stars1 week ago
This place is great. Cozy, tucked away, peaceful, beautiful surroundings. Valerie is easy to communicate and quick to respond. The instructions were clear.

Luxury chalet rentals

Guest favorite
A spacious great room features high ceilings with wooden beams and large triangular windows. A wooden dining table is situated near the windows, while comfortable seating arrangements with neutral-toned upholstery are arranged around a central fireplace. Natural light fills the space, enhancing the open concept design.
Chalet in Richmond
4.97 out of 5 average rating, 93 reviews

Updated Berkshires Chalet Mins to Tanglewood/Lenox

GlennRating, 5 stars9 months ago
This was our 2nd stay at this property. If you love the Berkshires and all the activities available, this house and property are perfect. It is very well maintained and the great room is perfect for our large family. Nothing like the hot tub and sitting around a fire after a busy day of hiking and Tanglewood. Wendy is an excellent host, never a problem.
Guest favorite
Chalet in Otis
4.91 out of 5 average rating, 65 reviews

Kayaks, Sauna & Family: Relax & Play

CarlaRating, 5 stars1 month ago
Lovely stay in western MA. Well furnished home with all the comforts of home. Loved the screened in eating porch and spent a good amount of time sitting around the large table. We had a lot of fun using the amenities like the sauna. Since it was a but early in the season we didn't get out on the lake but enjoyed the view and relaxing in nature.
Guest favorite
A modern mountain home is seen blanketed in fresh snow, featuring a distinctive blue roof. The spacious deck extends around the exterior, providing ample outdoor space. Tall trees frame the background, enhancing the feeling of seclusion amidst the winter landscape.
Chalet in New Marlborough
4.92 out of 5 average rating, 53 reviews

Modern Secluded Ski Chalet | 40 Acres | Family

JustinRating, 5 stars9 months ago
Absolutely amazing stay! I have never stayed with such hospitable and genuinely nice hosts. In addition their home was filled with interesting gadgets and beautiful aesthetic, they’ve inspired to replace every toilet in my house! I hope I have the pleasure of staying here again! Thank you Jennifer and Evan!
A spacious living area is centered around a unique circular fireplace, with large windows providing views of the lush surroundings. A comfortable curved sofa in light fabric is complemented by a natural wood coffee table, creating an inviting space for relaxation and gathering.
Chalet in Canaan
4.56 out of 5 average rating, 68 reviews

R3Bliss - Estate with Hot Tub, Tennis Court & Pool

RobinRating, 5 stars4 months ago
Great stay. Bathrooms r small and outdated but the fireplace and hot tub and property outweigh the cons.
A wrap-around deck is seen featuring a spacious outdoor seating area with plush couches and a coffee table. An umbrella offers shade over a dining area with chairs. Surrounding greenery enhances the tranquil atmosphere, with colorful planters visible along the edge.
Chalet in Monterey

New Listing - Fully Renovated Lake/Ski Chalet

SuzannaRating, 5 stars3 months ago
This is a great house in a nice location. It’s comfortable, warm, well stocked kitchen, the jacuzzi was a nice touch have. Garry was a good host who was responsive and easy to work with.

Destinations to explore