The Berkshires Romantic Vacations 2026

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 ...

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! (2,544 reviews)

"Place was clean and well equipped, pool and amenities were great too !"

Reviewed on 2026/8/17

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! (1,010 reviews)

Couples like: onsite spa services, bar, winery tours

Travelers say...

"Problems with elevators. Rooms were clean but in disrepair. Parking is abysmal due to exterior construction. Staff were good but working under tough conditions. Very overpriced for what we got"

Reviewed on 2026/8/16

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.