
Chalet holiday rentals in Berkshire County
Find and book unique chalets on Airbnb
Top-rated chalet rentals in Berkshire County
Guests agree: these chalets are highly rated for location, cleanliness and more.
0 of 0 items showing
1 of 3 pages
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for chalet rentals in Berkshire County
Family-friendly chalet rentals
Guest favourite

Chalet in Richmond
4.97 out of 5 average rating, 93 reviewsUpdated 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 favourite

Chalet in Peru
4.92 out of 5 average rating, 287 reviewsSwiss Chalet Style Timberframe Home in Berkshires
WilliamRating, 5 stars3 weeks 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 favourite

Chalet in New Marlborough
4.92 out of 5 average rating, 53 reviewsModern 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!

Chalet in Lee
4.83 out of 5 average rating, 65 reviewsWaterfront 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!

Chalet in Stephentown
5 out of 5 average rating, 13 reviewsSki 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.
Guest favourite

Chalet in Otis
4.94 out of 5 average rating, 417 reviewsMid-Century Glass Octagon in the Berkshires
ChelseaRating, 5 stars2 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 favourite

Chalet in Monterey
4.98 out of 5 average rating, 84 reviewsCozy French Country chalet
JacobRating, 5 stars5 days 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 favourite

Chalet in Richmond
4.97 out of 5 average rating, 93 reviewsUpdated 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 favourite

Chalet in Otis
4.91 out of 5 average rating, 65 reviewsKayaks, 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 favourite

Chalet in New Marlborough
4.92 out of 5 average rating, 53 reviewsModern 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!

Chalet in Hillsdale
5 out of 5 average rating, 3 reviewsCatamount Family Retreat - Walk to the Slopes
AlexandraRating, 5 stars3 weeks ago
Great house, perfect for our family. We stayed in the summer and it rained the whole time, but we still enjoyed it. The road is not very safe to walk on so definitely need a car to get around, but the restaurant right across the street at Little Cat was great. Overall really good place to stay, will be back

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
- House rentals Berkshire County
- Rentals with lake access Berkshire County
- Rentals with pools Berkshire County
- Private suite rentals Berkshire County
- Rentals with a patio Berkshire County
- Waterfront rentals Berkshire County
- Family-friendly rentals Berkshire County
- Cottage rentals Berkshire County
- Beachfront rentals Berkshire County
- Rentals with a sauna Berkshire County
- Rentals with breakfast Berkshire County
- Pet-friendly rentals Berkshire County
- Fitness-friendly rentals Berkshire County
- Rentals with a firepit Berkshire County
- Rentals with a fireplace Berkshire County
- Family-friendly rentals Berkshire County
- Rentals with a washing machine and dryer Berkshire County
- Bed and breakfasts Berkshire County
- Farm stay rentals Berkshire County
- Guest house rentals Berkshire County
- Rentals with an EV charger Berkshire County
- Ski-in/ski-out rentals Berkshire County
- Apartment rentals Berkshire County
- Rentals with outdoor seating Berkshire County
- Cabin rentals Berkshire County
- Rentals with a hot tub Berkshire County
- Flat rentals Berkshire County
- Rentals with a kayak Berkshire County
- Rentals with beach access Berkshire County
- Chalet rentals Massachusetts
- Chalet rentals United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Six Flags New England
- John Boyd Thacher State Park
- Albany Center Gallery
- Bushnell Park
- Jiminy Peak Mountain Resort
- Taconic State Park
- Berkshire East Mountain Resort
- Catamount Mountain Ski Resort
- Zoom Flume
- Kent Falls State Park
- Bash Bish Falls State Park
- Mount Greylock Ski Club
- Mount Snow Ski Resort
- Norman Rockwell Museum
- Beartown State Forest
- Mohawk Mountain Ski Area
- Hartford Golf Club
- Bright Nights at Forest Park
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Opus 40
- Naumkeag
- Brignole Vineyards
- Bousquet Mountain Ski Area