The Berkshires Romantic Holidays
Book a Hotel + Flight or Car together to unlock savings
Photo by Photo courtesy of Berkshire Visitors Bureau
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- Better togetherSave up to HK$7,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
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Shaker Mill Inn
2 Oak Street West Stockbridge MA
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! (455 reviews)
Wonderful place to stay!
Reviewed on 17 May 2026
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness centre and a 24-hour front desk. Our guests praise the helpful staff in their ...
8.8/10 Excellent! (2,361 reviews)
Room was dated and needed a refresh but was clean
Reviewed on 17 May 2026
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
Stay at this business-friendly hotel in Pittsfield. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
8/10 Very Good! (1,000 reviews)
Couples like: on-site spa services, bar, winery tours
Travellers 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 19 Apr 2026
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.
