Search Chalets in The Berkshires

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for The Berkshires chalets

Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
The price is AED 826
AED 1,020 total
includes taxes & fees
24 Mar - 25 Mar
Vikings Villages Resort - Double Bed Room

Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
9.8 out of 10, Exceptional, (10 reviews)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is AED 461
AED 1,615 total
includes taxes & fees
14 Apr - 15 Apr
Chalet Mount Snow/Stratton Skiing/hiking

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

Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike
Charlemont
10.0 out of 10, Exceptional, (1 review)
The price is AED 1,469
AED 3,282 total
includes taxes & fees
24 Mar - 25 Mar
Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike

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 AED 901
AED 2,400 total
includes taxes & fees
31 Mar - 1 Apr
NEW Private Chalet - 4 mins to Mt Snow

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)
"We had a great time at the Chalet. Great accommodations Jennifer made sure we had everything we needed She went above and beyond to accommodate our group. "
United States
Chris I.
The price is AED 2,020
AED 3,628 total
includes taxes & fees
9 Apr - 10 Apr
Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!

Private cabin: 7 mins to slopes, wood fireplace

Private cabin: 7 mins to slopes, wood fireplace
Dover
9.8 out of 10, Exceptional, (7 reviews)
"The host - Excellent communication and very accommodating!"
United States
Erika O.
The price is AED 514
AED 1,876 total
includes taxes & fees
20 Apr - 21 Apr
Private cabin: 7 mins to slopes, wood fireplace

Hot Tub, Theater & Game Rooms, Fire Pit, 1 mile to Mount Snow, nearby Moover bus

Hot Tub, Theater & Game Rooms, Fire Pit, 1 mile to Mount Snow, nearby Moover bus
Dover
10.0 out of 10, Exceptional, (12 reviews)
"Doug was very communicative and the home was beautiful!"
United States
Kate M.
The price is AED 638
AED 2,933 total
includes taxes & fees
24 Mar - 25 Mar
Hot Tub, Theater & Game Rooms, Fire Pit, 1 mile to Mount Snow, nearby Moover bus

A Charming Chalet with Hot Tub 1 Mile to Mt. Snow

A Charming Chalet with Hot Tub 1 Mile to Mt. Snow
Dover
10.0 out of 10, Exceptional, (17 reviews)
"This place was absolutely amazing! The pictures didn’t do this place justice. The ambience of the deck at night was magical. "
United States
Kaymari T.
The price is AED 1,098
AED 2,615 total
includes taxes & fees
6 Apr - 7 Apr
A Charming Chalet with Hot Tub 1 Mile to Mt. Snow

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
9.8 out of 10, Exceptional, (25 reviews)
"Decently-sized rooms, great lighting, plenty of space for families with kids to relax, enjoy the outdoor space, easy drive to Stratton and Wilmington. "
United States
SZU YIN C.
The price is AED 386
AED 1,602 total
includes taxes & fees
24 Mar - 25 Mar
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

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.
Private Luxurious Chalet with heated Pool,Hot Tub, Game Rooms. Pet-Friendly!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top The Berkshires Hotel Reviews