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 Ebenezer II Gifts and Antiques ...

9.6/10 Exceptional! (461 reviews)

"Really clean, comfortable, and quiet. The pastries and fruit they provided were delicious too !"

Reviewed on 2026/6/9

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! (2,396 reviews)

"I enjoy staying here . The front desk staff was very friendly . I like the hours of outdoor and indoor pool . My only complaints is the rooms are very very outdated and had to go to front desk every day because keys didnt work ."

Reviewed on 2026/6/15

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! (1,010 reviews)

Couples like: onsite spa services, bar, winery tours

Travelers say...

"There is a lot of construction going on outside which resulted in no parking. You have to park at the bank lot next door. This in itself was tollerable, however, the check-in/unloading, and check-out/loading was a nightmare with no parking near the entry way. There was room for cars but the manager ..."

Reviewed on 2026/6/15

See all 1,082 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.