Photo by Photo courtesy of Berkshire Visitors Bureau

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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 Jun 22, 2026

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 Jul 1, 2026

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 Jun 30, 2026

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.