Photo by Photo courtesy of Berkshire Visitors Bureau

Plan, book, travel with confidence

Better together

Save up to ₩234,741 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 breakfast, free parking, and daily housekeeping. Popular attractions Tanglewood Music Center and Ebenezer II ...

9.6/10 Exceptional! (402 reviews)

Brief stay. Was decent. Didnt get to see much more than the room itself

Reviewed on Oct 28, 2025

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.

8.6/10 Excellent! (2,106 reviews)

Good location; reasonable price; very clean and quiet - would definitely return

Reviewed on Oct 27, 2025

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.

7.8/10 Good! (928 reviews)

Couples like: onsite spa services, bar, winery tours

Travelers say...

Everything is clean

Reviewed on Oct 27, 2025

See all 1,104 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.