The Berkshires Romantic Holidays

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Shaker Mill Inn
Shaker Mill Inn
2.5 out of 5
2 Oak Street, West Stockbridge, MA
  • 25 min walk from Tanglewood Music Center
Stay at this property in West Stockbridge. Enjoy free breakfast, free parking, and daily housekeeping. Popular attractions Tanglewood Music Center and Ebenezer ...
9.6/10 Exceptional! (385 reviews)
"Very cute and clean room. After driving all day we were so happy to see all muffins, scones, yogurt, cereal, oatmeal, strawberries, milk, OJ, hot chocolate and coffee already in the room for breakfast the next day. We had a great stay, thank you!"

Reviewed on 2 Jul 2025

Shaker Mill Inn
Vacation Village in the Berkshires
Vacation Village in the Berkshires
3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
  • 35 min drive from Tanglewood Music Center
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! (1,856 reviews)
"This is more like renting a small condo, though I booked it as a "hotel room". Lots of families, plenty for them to do on premises, barbeque pits, activities, multiple pools and water features for the kids. It is a massive development at the foot of a ski resort in rural Western Massachusetts. The ..."

Reviewed on 6 Jul 2025

Vacation Village in the Berkshires
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHG
3 out of 5
One West Street, Pittsfield, MA
  • 16 min drive from Tanglewood Music Center
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! (816 reviews)

Couples like: on-site spa services, bar, winery tours

Travellers say...
"Clean but needs renovations"

Reviewed on 8 Jul 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG
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.