Photo by Photo courtesy of Berkshire Visitors Bureau

Plan, book, travel with confidence
Better together
Save up to NT$25,000 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 Romantic The Berkshires Hotels

Shaker Mill Inn

2 Oak Street West Stockbridge MA

25 min walk from Tanglewood Music Center

Stay at this B&B in West Stockbridge. Enjoy free parking and daily housekeeping. Popular attractions Tanglewood Music Center and National Shrine of the Divine ...

9.6/10 Exceptional! (462 reviews)

"The room we had was spacious, and there are nice outdoor sitting areas. Breakfast is placed in your refrigerator and in a basket the day before. If you are hoping for a charming Berkshire bed and breakfast with a cooked breakfast and interaction with your host, you will be disappointed. If you are ..."

Reviewed on 2026/6/22

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

35 min drive from Tanglewood Music Center

A garden and in-room fireplaces await at this romantic condo, which also offers a terrace and an outdoor pool.

8.8/10 Excellent! (2,414 reviews)

"Clean large room- some wear on the kitchen cabinets and the bathroom door stuck check in was a bit of a challenge. Otherwise good"

Reviewed on 2026/7/1

Holiday Inn & Suites Pittsfield-Berkshires by IHG

One West Street Pittsfield MA

16 min drive from Tanglewood Music Center

A garden and onsite dining await at this romantic hotel, which also offers a terrace and a bar.

8/10 Very Good! (1,000 reviews)

Couples like: onsite spa services, bar, winery tours

Travelers say...

"Honestly, this place should close for renovations. It's a mess. • 1 working elevator for a 12-floor hotel. The elevator is used by staff (and their equipment) and guests. Elevator wait times were 10+ minutes. Watched a delivery guy? guest? employee? get on the elevator with a large e-bike. Plus side ..."

Reviewed on 2026/6/30

See all 1,090 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.