Chalet vacation rentals in Berkshire County

An expansive deck is surrounded by lush greenery, featuring outdoor seating and a dining area. Warm café lights hang overhead, creating a cozy atmosphere. A person is seen grilling at a gas grill, while another enjoys a meal at a table, capturing a serene outdoor experience.

4.95 out of 5 average rating, 411 reviews

Mid-Century Glass Octagon in the Berkshires

AishwaryaRating, 5 stars3 weeks ago

Katherine's home is absolutely stunning. It is very thoughtfully put together and has the most welcoming vibe. We were there for the weekend and it was one of the most peaceful getaways that allowed us to connect with ourselves and our creativity. I would recommend this Airbnb to everyone. We will definitely be booking this stay again :)

4.96 out of 5 average rating, 69 reviews

A spacious living area features a warm wooden ceiling with exposed beams. A light-colored sectional sofa is arranged with decorative pillows, accompanied by a glass coffee table. A stone fireplace adds a rustic element, complemented by green plants placed around the room.

Chalet in Averill Park

A Hidden Sparrow

JohnRating, 5 stars1 week ago

What a gorgeous home. Quality inside and outside. One of the most peaceful places, pure bliss and beauty everywhere. This home celebrates that spectacular view and provides a space to relax and rejuvenate. So tastefully decorated, every detail was considered with special extras here and there. The beds were exceptionally comfortable. The sofas were pleasantly cozy. The kitchen and pantry were well appointed. The overall space was shining with cleanliness. We were a group of 5, we all felt comfortable, loved our private bedrooms and the cozy space for family gatherings. The convivial atmosphere left us excited to plan our next gathering. Joshua and Hugo were communicative and accommodating, they even let us check in early! Thank you for the use of your home. We had an amazing weekend.

Superhost

A spacious living area features high ceilings and large windows that allow natural light to fill the room. A wood stove stands against a stone wall, and various seating options are provided, complemented by layered rugs. Bookshelves are visible in the background, adding a cozy touch.

Chalet in Lenox

4.82 out of 5 average rating, 22 reviews

Peaceful Chalet in the Woods: Walk to Lenox

DanielaRating, 5 stars2 months ago

Simeon and Anna's place is beautiful! They made me feel right at home. My stay was amazingly peaceful which is exactly what I was looking for. the chalet is centrally located so everything is easy to get to. I recommend this place to anyone sifting through Airbnb listings, you will not be disappointed. beautiful place beautiful setting, and very convenient! I will be back! Thank you, Simeon and Anna, for sharing such an awesome place.

A cozy loft area features a plush armchair positioned near large triangular windows. Natural light floods the space, highlighting the warm wood paneling of the sloped ceiling. A small table with a book is nearby, creating a perfect spot for relaxation.

4.9 out of 5 average rating, 63 reviews

Kayaks, Sauna & Family: Relax & Play

MegRating, 5 stars1 month ago

Clemence's place is gorgeous and comfortable! Perfect stay for our group of friends catching up for the weekend. Super clean, the kitchen is extremely well stocked - much better than shows in the photos or is listed in the description. Private spot with plenty of space. Had a lovely walk in a nearby state park, too.

5 out of 5 average rating, 12 reviews

Chalet in Canaan

SRC-Hudson Valley/Berkshires Cultural Corridor

CariRating, 5 stars4 months ago

If you're thinking about booking Kristen's Chalet - do not hesitate! Book it - you won't be disappointed. The house has ample room to spread out with your family. We enjoyed our Christmas dinner at the dining table and afterwards, we were able to watch a movie together. The location was perfect for us to go out every day and explore - Red Lion Inn, The Mount and several other towns. We had to make plans to stay in so we could enjoy the beautiful Chalet for an evening. We can not wait to return and enjoy this beautiful home. ♡

A serene wooded area is depicted, featuring tall trees with sunlight filtering through the branches. A calm stream reflects the surrounding greenery and sky, creating a peaceful natural setting within the 120-acre property.

Chalet in Stephentown

5 out of 5 average rating, 13 reviews

Ski Cottage in the Berkshire hills

WendyRating, 5 stars32 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.

Chalet in New Marlborough

4.92 out of 5 average rating, 53 reviews

Modern Secluded Ski Chalet | 40 Acres | Family

JustinRating, 5 stars7 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!

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Apartments

Convenient locations with everyday essentials

Houses

A space thats all yours, with room for everyone

Popular amenities for Berkshire County chalet rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly chalet rentals

4.97 out of 5 average rating, 93 reviews

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

Updated Berkshires Chalet Mins to Tanglewood/Lenox

GlennRating, 5 stars8 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.

4.92 out of 5 average rating, 284 reviews

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

Swiss Chalet Style Timberframe Home in Berkshires

LauraRating, 5 stars1 month ago

This is my favorite rental. It is so cozy and open at the same time. There is plenty of space for everyone with two twin beds, a king bed in the loft, a fold out sofa and a queen bedroom downstairs for my daughter. The woods are beautiful and the house is in a quiet location. At the same time, it is not too far from the Allendale shopping area in Pittsfield, small stores in Hinsdale, as well as Williamsburg and Northampton. The house is very warm even in the winter, comes with everything you need to cook, and has laundry. The bedrooms are comfortable and bathrooms are nice. The TV and WIFI streaming work great. There is an extra long table which we use for games and a deck overlooking the backyard. Overall, it is a great place to stay for families.

Chalet in New Marlborough

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.

4.92 out of 5 average rating, 53 reviews

Modern Secluded Ski Chalet | 40 Acres | Family

JustinRating, 5 stars7 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 stars8 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 stars32 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.

Two adjoining spaces are shown, revealing a serene bedroom with a spacious bed and a cozy seating area featuring an accent chair. Natural light filters through large windows, highlighting the light-colored walls and wooden flooring. A decorative plant adds a touch of greenery.

Chalet in Canaan

4.67 out of 5 average rating, 66 reviews

R3Bliss - Estate with Hot Tub, Tennis Court & Pool

RobinRating, 5 stars2 months ago

Great stay. Bathrooms r small and outdated but the fireplace and hot tub and property outweigh the cons.

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.

4.95 out of 5 average rating, 411 reviews

Mid-Century Glass Octagon in the Berkshires

AishwaryaRating, 5 stars3 weeks ago

Katherine's home is absolutely stunning. It is very thoughtfully put together and has the most welcoming vibe. We were there for the weekend and it was one of the most peaceful getaways that allowed us to connect with ourselves and our creativity. I would recommend this Airbnb to everyone. We will definitely be booking this stay again :)

4.98 out of 5 average rating, 83 reviews

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

Cozy French Country chalet

NoamRating, 5 stars2 months ago

Always so great. Thanks so much. A wonderful house and a wonderful host.

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Luxury chalet rentals

4.97 out of 5 average rating, 93 reviews

An open concept great room features high cathedral ceilings and large windows allowing natural light to fill the space. A dining table is positioned near the kitchen, with seating for several. Comfortable seating surrounds a media area, creating a welcoming atmosphere for relaxation.

Chalet in Richmond

Updated Berkshires Chalet Mins to Tanglewood/Lenox

GlennRating, 5 stars8 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.

4.9 out of 5 average rating, 63 reviews

Kayaks, Sauna & Family: Relax & Play

MegRating, 5 stars1 month ago

Clemence's place is gorgeous and comfortable! Perfect stay for our group of friends catching up for the weekend. Super clean, the kitchen is extremely well stocked - much better than shows in the photos or is listed in the description. Private spot with plenty of space. Had a lovely walk in a nearby state park, too.