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! (465 reviews)

"The Shaker Mill Inn is located in West Stockbridge so it is away from the dense tourist traffic in Stockbridge, but is located with easy access to Tanglewood, Stockbridge, Norman Rockwell Museum, and I90 and the rural Berkshires. The garden was wonderful with many flowers in bloom—very pretty. The ..."

Reviewed on Jul 27, 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 aparthotel, which also offers a terrace and an outdoor pool.

8.8/10 Excellent! (2,490 reviews)

"Great place but sometimes have issues connecting with Expedia reservations it seems."

Reviewed on Aug 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.

7.8/10 Good! (1,006 reviews)

Couples like: onsite spa services, bar, winery tours

Travelers say...

"Three elevators with only one of them working, the entire time I was there. There are stairs which I used once from my 5th floor room, but then discovered the stairwell does not open on the 2nd floor and the second floor is where the restaurant, bar, gym and everything else you might want are located. ..."

Reviewed on Aug 1, 2026

See all 1,086 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.