
The Berkshires Holidays
Photo by Photo courtesy of Berkshire Visitors Bureau
- Plan, book, travel with confidence
Better together
Save up to €185 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Top hotels in The Berkshires

Vacation Village in the Berkshires
276 Brodie Mountain Rd, Williamstown, MA
Fully refundableReserve now, pay when you stay
The price is €111 per night from 7 Sept to 8 Sept
€111
7 Sept - 8 Sept
includes taxes & fees
8.6/10 Excellent! (1,963 reviews)
"If your hiking Mt Greylock this is a fantastic location. We arrived late and left early so we didn't get to use anything on the property but it did look at nice place for families to stay it. We did sit by the outdoor fire pit for a while which was cool."
Reviewed on 21 Aug 2025

Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (590 reviews)
"Flexible dates, reasonable price, old but clean"
Reviewed on 24 Aug 2025

Quality Inn
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
Fully refundableReserve now, pay when you stay
The price is €88 per night from 7 Sept to 8 Sept
€88
7 Sept - 8 Sept
includes taxes & fees
8.2/10 Very Good! (1,002 reviews)
"Great location and close enough to walk to shops and restaurants."
Reviewed on 22 Aug 2025
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.
Popular places to visit

Tanglewood Music Center
You can make plans for a show at Tanglewood Music Center during your stay in Lenox. While you're in the area, stroll along the lakeside.
National Shrine of the Divine Mercy
Learn about the local history of Stockbridge when you spend time at National Shrine of the Divine Mercy. While you're in the area, stroll along the lakeside.
Naumkeag Museum
You can spend time studying the exhibits at Naumkeag Museum in Stockbridge. While you're in the area, stroll along the lakeside.
Frequently asked questions
More trip options
Expedia's Latest Trends
Hotels
Flights
Activities
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.