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 breakfast, free parking, and daily housekeeping. Popular attractions Tanglewood Music Center and National Shrine ...

9.6/10 Exceptional! (449 reviews)

Loved all of it! We had the garden room and it had everything you needed. Was clean and comfy, breakfast supplied in your room along with coffee, microwave, toaster oven, refrigerator and private deck - we will definitely be back.

Reviewed on 2026/4/30

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! (2,343 reviews)

Great place, nice staff, large rooms, very nice and clean place.

Reviewed on 2026/5/1

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...

Staff was nice. Room was clean. Parking lot was under construction. Had to park offsite. Wasn't a total inconvenience. One elevator was broken and the wait time was long each time we were trying to use.

Reviewed on 2026/4/19

See all 1,124 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.