The Berkshires Romantic Holidays
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Photo by Photo courtesy of Berkshire Visitors Bureau
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- Better togetherSave up to RM 324 when you book a flight and hotel together*
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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 Ebenezer II Gifts and Antiques and Hotchkiss ...
9.6/10 Exceptional! (408 reviews)
Super friendly & the room is adorable! Simple check in. The room was spotlessly clean. We had a great stay. Thank you!
Reviewed on 11 Dec 2025
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 ...
8.6/10 Excellent! (2,170 reviews)
Awesome for ski
Reviewed on 14 Dec 2025
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! (984 reviews)
Couples like: on-site spa services, bar, winery tours
Travellers say...
Clean and comfortable
Reviewed on 7 Dec 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.
