Search Chalets in The Berkshires from CA $483

  • 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

Check prices for these dates

In two weeks
Jul 10 - Jul 12
In two months
Aug 21 - Aug 23
In three months
Sep 18 - Sep 20
In four months
Oct 16 - Oct 18

Our top choices for The Berkshires chalets

Exterior

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

4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Dover
9.6 out of 10, Exceptional, (27 reviews)
"Very clean - kitchen well stocked with utensils for cooking - great proximity to Mount Snow."
United States
Brian S.
The price is CA $151
CA $622 total
includes taxes & fees
Jun 24 - Jun 25
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Exterior

Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
10.0 out of 10, Exceptional, (11 reviews)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is CA $99
CA $537 total
includes taxes & fees
Jun 23 - Jun 24
Chalet Mount Snow/Stratton Skiing/hiking
Exterior

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

Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!
Dover
10.0 out of 10, Exceptional, (7 reviews)
"Perfect spot for a family ski vacation! Thanks you for behind a great host!"
United States
Andrew B.
The price is CA $778
CA $1,417 total
includes taxes & fees
Jun 23 - Jun 24
Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!
Exterior

Private Luxurious Chalet with heated Pool,Hot Tub, Game Rooms. Pet-Friendly!

Private Luxurious Chalet with heated Pool,Hot Tub, Game Rooms. Pet-Friendly!
Cropseyville
10.0 out of 10, Exceptional, (3 reviews)
"Wonderful home and property. Stayed for a family wedding weekend. The home, hot tub and pool were a perfect way to relax before and after the ceremony."
United States
Patrick H.
The price is CA $2,829
CA $4,661 total
includes taxes & fees
Jun 29 - Jun 30
Private Luxurious Chalet with heated Pool,Hot Tub, Game Rooms. Pet-Friendly!
Exterior

NEW Private Chalet - 4 mins to Mt Snow

NEW Private Chalet - 4 mins to Mt Snow
Dover
10.0 out of 10, Exceptional, (3 reviews)
"Great place close enough to everything you need but set off the road for quiet evenings. Clean, spacious open floor plan great accommodation that checks all the needs for a ski getaway. "
United States
Mark C.
The price is CA $347
CA $942 total
includes taxes & fees
Jun 23 - Jun 24
NEW Private Chalet - 4 mins to Mt Snow
Terrace/patio

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

Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike MTB Rafting
Charlemont
10.0 out of 10, Exceptional, (2 reviews)
"Our stay at the chalet was exactly what we hoped it would be! The space is in a beautiful location that is perfect for dogs. The host was very helpful and responsive and check in was a breeze. We'll be back for sure!"
United States
Georgia P.
The price is CA $510
CA $1,911 total
includes taxes & fees
Jun 23 - Jun 24
Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike MTB Rafting
Exterior

Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
The price is CA $389
CA $483 total
includes taxes & fees
Jun 23 - Jun 24
Vikings Villages Resort - Double Bed Room
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top The Berkshires Hotel Reviews

The Red Lion Inn

The Red Lion Inn

8/10 Good
"I did not stay in the main building but had a room in a separate building on the same block. I quite liked my room away from the inn. It was roomy, quiet, across the street from a church, easy walk to the cafe, and there was a bunny 🐰 eating grass outside each night. I think I will request such a room away from the hubbub when I return. The food at the Red Lion's Inn's 'Widow's' tavern was delicious. Just know the buildings are indeed OLD so if you are seeking great water pressure or modern vibe, this is not your place. Love the history of this place!"
Tina 5-night trip
Posted less than an hour ago
The Red Lion Inn

Find out more about The Berkshires

The Berkshires Chalets information

Number of reviews
53
Accommodation
2 Chalets
Lowest Price
CA $483
Highest Price
CA $4,661

Explore a world of travel with Expedia