The Berkshires Chalets from CA $123

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Find vacation rentals that suit your style

Check prices for these dates

Next weekend

In two weeks

In one month

In two months

Our top choices for The Berkshires chalets

A wooden building with a thatched roof and a wooden deck leading to it.

1. Vikings Villages Resort - Double Bed Room

Guilford

CA $449 total

includes taxes & fees

Nov 8 - Nov 9

A view of a forested area with a bench in the foreground.

2. Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike MTB Rafting

Charlemont

Georgia P.

CA $1,757 total

includes taxes & fees

Nov 16 - Nov 17

A wooden house with a porch lit by string lights, surrounded by snow.

3. Chalet Mount Snow/Stratton Skiing/hiking

East Dover

Chelsea G.

CA $533 total

includes taxes & fees

Nov 8 - Nov 9

A large, single-story house with a symmetrical roof and a central chimney, surrounded by a well-maintained lawn and dense forest with autumn foliage.

4. Sleeps 16 Chalet: Pool, Hot Tub, Game Rooms. Pet-Friendly.

Cropseyville

Patrick H.

CA $2,440 total

includes taxes & fees

Dec 2 - Dec 3

A two-story wooden house with a stone retaining wall, a covered porch, and a small shed.

5. 4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

Dover

Brian S.

CA $690 total

includes taxes & fees

Nov 30 - Dec 1

A hot tub on a wooden deck with a view of autumn trees.

6. Chalet 1mi to Mount Snow with cinema and hot tub

Dover

Liz E.

CA $1,059 total

includes taxes & fees

Nov 10 - Nov 11

7. NEW Private Chalet - 4 mins to Mt Snow

Dover

Mark C.

CA $905 total

includes taxes & fees

Nov 8 - Nov 9

A two-story house with a large deck and a covered porch, surrounded by trees and a grassy yard.

8. Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!

Dover

Andrew B.

CA $730 total

includes taxes & fees

Nov 9 - Nov 10

View all properties

Learn more about The Berkshires

Tucked in western Massachusetts, this region blends culture and nature with world-class museums and lush hiking trails. Catch a summer concert at Tanglewood, explore Norman Rockwell's art in Stockbridge, or ski the slopes at Jiminy Peak in nearby Hancock.

See all hotels in The Berkshires

A large white building with multiple chimneys, surrounded by lush gardens with various flowers.

Top reviews in The Berkshires

A large, two-story white building with a symmetrical facade, columns, and a central entrance.

Granville House

Housatonic

10/10 Excellent

Rebecca

A large, two-story house with a well-maintained lawn and a fence.

Devonfield Inn B&B

Lee

10/10 Excellent

We stayed at the Devonfield Inn in mid-October during peak foliage season. The hotel is a wonderful historic home built in 1800 with much of its historic character preserved. Our hosts were so welcoming and made us feel at home. The room was very comfortable and breakfast was fantastic. In the morning, we got a special surprise to see a bear on the patio drinking from the fountain and robbing the bird feeder. Overall we highly recommend the Devonfield. We will definitely go back.

Lise