Photo by Photo courtesy of Berkshire Visitors Bureau
Search Chalets in The Berkshires
Change your mindBook hotels with free cancellation
Be pickySearch 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
Chalet in Guilford
Vikings Villages Resort - Double Bed RoomThe price is AU$553
includes taxes & fees
11 Dec - 12 Dec
Chalet in West Dover
8 Minutes to ski Mount Snow, Hot Tub, Game Room, Fire Pit, Dog friendly10.0 out of 10, Exceptional, (20)
"Had a delightful time here for the Holiday. Quiet place which held us all comfortably! Easy to get to the places we wanted to go to and was well maintained. Communication with the hosts was fantastic."
Jeannine A.
The price is AU$919
includes taxes & fees
15 Dec - 16 Dec
Chalet in East Dover
Mountain Chalet mins from Mt Snow Skiing/hiking9.8 out of 10, Exceptional, (9)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
Roy-michael G.
The price is AU$606
includes taxes & fees
11 Dec - 12 Dec
9.8 out of 10, Exceptional, (22)
"Decently-sized rooms, great lighting, plenty of space for families with kids to relax, enjoy the outdoor space, easy drive to Stratton and Wilmington. "
SZU YIN C.
The price is AU$645
includes taxes & fees
5 Jan - 6 Jan 2026
Chalet in Dover
A Charming Chalet with Hot Tub 1 Mile to Mt. Snow10.0 out of 10, Exceptional, (14)
"Place was super clean. My wife’s favorite video game pac man was down stairs which gave us all a chance to compete against each other and was a blast. We would love to go back A on this property "
Rich H.
The price is AU$1,083
includes taxes & fees
15 Dec - 16 Dec
Chalet in Dover
NEW Private Chalet - 4 mins to Mt Snow10.0 out of 10, Exceptional, (2)
"Mary and Adam were absolutely lovely hosts! From the initial booking to check-in and throughout our stay, they were incredibly responsive. The house was fantastic—completely updated, with a fully equipped kitchen, spacious bedrooms, and a beautiful living area with a cozy fireplace.Our only regret is that we couldn’t stay longer. Thank you, Mary and Adam, for a wonderful stay!"
Patricia N.
The price is AU$1,014
includes taxes & fees
11 Dec - 12 Dec
Chalet in Charlemont
Joia Verde Chalet—Sleeps 8, Berkshire east ski haven on 127 secluded acresThe price is AU$1,173
includes taxes & fees
11 Dec - 12 Dec
10.0 out of 10, Exceptional, (4)
"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. "
Chris I.
The price is AU$983
includes taxes & fees
7 Jan - 8 Jan 2026
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.
Top The Berkshires Hotel Reviews
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
10/10 Excellent
Find out more about The Berkshires
The Berkshires Chalets information
Number of reviews | 75 |
|---|---|
Accommodation | 2 Chalets |
Lowest Price | AU$553 |
Highest Price | AU$1,502 |
Explore a world of travel with Expedia
- B&B in Alford
- Cheap Hotels in Alford
- Alford Hotels
- Villas in Alford
- Beach Hotels in Becket
- Cheap Hotels in Becket
- Hotels with Parking in Becket
- Cheap Hotels in Blandford
- Luxury Hotels in Blandford
- Ski Hotels in Blandford
- Blandford Hotels
- B&B in Chester
- Chester Hotels
- Guest Houses in Granville
- Holiday Homes in Granville
- Cheap Hotels in Granville
- Granville Hotels
- Motels in Granville
- Great Barrington Hotels
- Motels in Great Barrington
- Huntington Hotels
- Castles in Lee
- Lgbt Welcoming Hotels in Lee
- Lee Hotels
- Cottages in Lenox
- Boutique Hotels in Lenox
- Cheap Hotels in Lenox
- Lenox Hotels
- Inns in Lenox
- Caravan Parks in Mill River
- B&B in Monterey
- Condominium Resort in Monterey
- Cheap Hotels in Monterey
- Family Hotels in Monterey
- Monterey Hotels
- Resort in Monterey
- Mount Washington Hotels
- Hotels near National Shrine of the Divine Mercy
- Caravan Parks in New Marlborough
- Farmstay in New Marlborough
- Beach Hotels in New Marlborough
- Luxury Hotels in New Marlborough
- Spa Hotels in New Marlborough
- Winery Hotels in New Marlborough
- New Marlborough Hotels
- Lodges in New Marlborough
- Motels in New Marlborough
- Apartments in Otis
- Caravan Parks in Otis
- Holiday Homes in Otis
- Otis Hotels
- Lodges in Otis
- Hotels near Otis Ridge
- B&B in Russell
- Holiday Homes in Russell
- Family Hotels in Russell
- Russell Hotels
- Inns in Russell
- B&B in Sheffield
- Caravan Parks in Sheffield
- Historic Hotels in Sheffield
- Spa Hotels in Sheffield
- Sheffield Hotels
- Motels in Sheffield
- Sherwood Forest Hotels
- Hotels with Parking in South Egremont
- South Egremont Hotels
- Southfield Hotels
- Historic Hotels in Stockbridge
- Stockbridge Hotels
- Hotels near Tanglewood Music Center
- Hotels near The Mount
- Luxury Hotels in Tolland
- Tolland Hotels
- Tyringham Hotels
- Lodges in Tyringham
- B&B in Washington
- Washington Hotels
- West Stockbridge Hotels