The Berkshires Romantic Holidays
Book a Hotel + Flight or Car together to unlock savings
Photo by Photo courtesy of Berkshire Visitors Bureau
- Plan, book, travel with confidence
- 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 National Shrine of the Divine ...
9.6/10 Exceptional! (462 reviews)
"The room we had was spacious, and there are nice outdoor sitting areas. Breakfast is placed in your refrigerator and in a basket the day before. If you are hoping for a charming Berkshire bed and breakfast with a cooked breakfast and interaction with your host, you will be disappointed. If you are ..."
Reviewed on 22 Jun 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! (2,414 reviews)
"Clean large room- some wear on the kitchen cabinets and the bathroom door stuck check in was a bit of a challenge. Otherwise good"
Reviewed on 1 Jul 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...
"Honestly, this place should close for renovations. It's a mess. • 1 working elevator for a 12-floor hotel. The elevator is used by staff (and their equipment) and guests. Elevator wait times were 10+ minutes. Watched a delivery guy? guest? employee? get on the elevator with a large e-bike. Plus side ..."
Reviewed on 30 Jun 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.
