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! (415 reviews)
Everything was great— the cleanliness, the plentiful breakfast, the character and coziness, and the proximity to Amici across the street (free dessert with your room key).
Reviewed on 13 Jan 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 ...
8.6/10 Excellent! (2,217 reviews)
Everything was great, the staff, the room, and the amenities. We will be coming back.
Reviewed on 25 Jan 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...
generally good
Reviewed on 19 Jan 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.
