Search Chalets in The Berkshires
- Plan, book, stay with confidence
Be picky
Search almost a million properties worldwide
Change your mind
Book hotels with free cancellation
Check prices for these dates
Next weekend
In two weeks
In one month
In two months
Compare 3 Chalets in The Berkshires with updated reviews, rates, and availability.

Berkshires Hilltop Retreat w Magic View! 15 mins to Ski Butternut.
Berkshires Hilltop Retreat w Magic View! 15 mins to Ski Butternut.
9.8 out of 10, Exceptional, (23)

Little Longbow Lakefront Chalet
Little Longbow Lakefront Chalet
9.2 out of 10, Wonderful, (10)
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
Other property types in The Berkshires

Vacation Village in the Berkshires
Vacation Village in the Berkshires
8.6 out of 10, Excellent, (1792)
The price is SAR 484
SAR 572 total
includes taxes & fees
25 Mar - 26 Mar

Jiminy Peak Mountain Resort
Jiminy Peak Mountain Resort
8.2 out of 10, Very Good, (925)
The price is SAR 559
SAR 613 total
includes taxes & fees
1 Apr - 2 Apr

The Ponds at Foxhollow
The Ponds at Foxhollow
8.6 out of 10, Excellent, (120)
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.
Recent reviews of The Berkshires hotels
Recent reviews of The Berkshires hotels

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
5/5 Excellent
"Lovely receptionist"
A verified traveler stayed at Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Posted 2 days ago
Explore a world of travel with Expedia
Explore a world of travel with Expedia
More Accommodation Types in The Berkshires
- Vacation Homes in The Berkshires
- Apartments in The Berkshires
- Cottages in The Berkshires
- Condo Rentals in The Berkshires
- Resorts in The Berkshires
- Motels in The Berkshires
- B&B in The Berkshires
- Cabin Rentals in The Berkshires
- Farmstay in The Berkshires
- Inns in The Berkshires
- Guest Houses in The Berkshires
- Aparthotels in The Berkshires
- Villas in The Berkshires
- Condo Resorts in The Berkshires
- Lodges in The Berkshires
- Hotels