The Berkshires Romantic Vacations

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Top Romantic The Berkshires Hotels

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 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! (461 reviews)
"Really clean, comfortable, and quiet. The pastries and fruit they provided were delicious too !"

Reviewed on 2026/6/9

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
A garden and in-room fireplaces await at this romantic condo, which also offers a terrace and an outdoor pool.
8.8/10 Excellent! (2,396 reviews)
"I enjoy staying here . The front desk staff was very friendly . I like the hours of outdoor and indoor pool . My only complaints is the rooms are very very outdated and had to go to front desk every day because keys didnt work ."

Reviewed on 2026/6/15

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
A garden and onsite dining await at this romantic hotel, which also offers a terrace and a bar.
8/10 Very Good! (1,010 reviews)

Couples like: onsite spa services, bar, winery tours

Travelers say...
"There is a lot of construction going on outside which resulted in no parking. You have to park at the bank lot next door. This in itself was tollerable, however, the check-in/unloading, and check-out/loading was a nightmare with no parking near the entry way. There was room for cars but the manager ..."

Reviewed on 2026/6/15

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.