The Berkshires Romantic Holidays
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Photo by Photo courtesy of Berkshire Visitors Bureau
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Shaker Mill Inn
2 Oak Street, West Stockbridge, MA
Stay at this B&B in West Stockbridge. Enjoy free breakfast, free parking, and daily housekeeping. Popular attractions Tanglewood Music Center and Ebenezer II ...
9.6/10 Exceptional! (392 reviews)
"Very casual and easy check in and out; lovely and substantial breakfast"
Reviewed on 11 Aug 2025
Vacation Village in the Berkshires
276 Brodie Mountain Rd, Williamstown, MA
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...
8.6/10 Excellent! (1,946 reviews)
"Very nice"
Reviewed on 15 Aug 2025
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street, Pittsfield, MA
Stay at this 3-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
7.8/10 Good! (860 reviews)
Couples like: on-site spa services, bar, winery tours
Travellers say...
"This is my "go to" when I'm in Pittsfield. It's central, convenient, clean and comfortable."
Reviewed on 17 Aug 2025
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.