Photo by Photo courtesy of Berkshire Visitors Bureau

Plan, book, travel with confidence
Better together
Save up to AU$2,500 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 Fishing The Berkshires Hotels

Harbour House Inn

725 North State Road Cheshire MA

37 min drive from Tanglewood Music Center

Stay at this B&B in Cheshire. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Adams Theater and Mount Greylock State Reservation Visitor ...

9.4/10 Exceptional! (55 reviews)

"No detail to my comfort was missed! The innkeeper had fresh baked goodies every afternoon and hot breakfast made from scratch. The historic property is beautiful and convenient to so many art galleries, sweet towns, trails and Tanglewood. Highly Recommended!!"

Reviewed on 4 July 2026

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

26 Glendale Road, RR 183 Stockbridge MA

12 min drive from Tanglewood Music Center

Stay at this luxury B&B in Stockbridge. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions National Shrine of the Divine Mercy and Tanglewood ...

9.2/10 Wonderful! (112 reviews)

"Our stay at The Inn was wonderful. Diane and staff could not have been more welcoming or helpful with great suggestions. Shopping and picnic supplies were spot on! Breakfast was delicious and more than plentiful. The pool was not available at this time, but what a beautiful setting. We’ll stay here ..."

Reviewed on 30 June 2026

1896 House Country Inn & Motels

910 Cold Spring Road Williamstown MA

57 min drive from Tanglewood Music Center

Stay at this hotel in Williamstown. Enjoy free parking, a business centre and a garden. Popular attractions Sheep Hill and Bullock Ledge Wildlife Management ...

6.6/10 (451 reviews)

"They canceled my stay due to alleged electrical issues. Saw a full lot n there the next morning. My stay would have been $260 for two nights. I was referred to two places about 15 miles v away. One was $650 and the other over $800. I remain suspicious of the situation."

Reviewed on 28 June 2026

See all 1,093 properties in The Berkshires

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.