Call us free on 0800 270 0069 We are open today between 9am and 5:30pm

Home/USA Holidays/USA Destinations/Massachusetts/The Berkshires

The Berkshires

This historic region offers a wealth of memorable events and activities framed by breathtaking natural beauty. The Berkshires feature year-round culture, recreation, and adventure in quaint towns like Stockbridge, Lenox, and Williamstown, while North Adams has the fabulous Museum of Contemporary Art.

Berkshires Church

Old Farm in the Berkshires

Rural scene in the berkshires

Williamstown in Fall

Berkshires Farms

There is no shortage of places to stay , shop, and dine. Great ziplines and canopy tours are here; for all-day fun, visit Look Park with a zoo, lake, water spray park, 18 holes of miniature golf and six tennis courts. In winter, family-friendly skiing and other snow sports are just a short walk uphill.

The Berkshires Experiences

We have put together some of the best day trips available from The Berkshires-from ziplining to expansive outdoor areas and more.These are all available on our USA holidays including The Berkshires. Contact our experts to add them on to your holiday.

The Berkshires Experiences

The Berkshires Experiences

The Berkshires Holidays

Below is a small selection of The Berkshires holidays we offer. If you would like us to create a USA holiday including The Berkshires just for you, give us a call.

Best of New England Fly Drive

  • Boston
  • Portland Maine
  • Bar Harbor
  • White Mountains
  • Killington
  • The Berkshires
  • Mystic
  • Yarmouth MA
  • Visit beautiful maritime towns
  • See the beautiful mountains of New Hampshire & Vermont
  • Experience historic Boston

14 Nights from £3430pp

more details

Hotels in The Berkshires

Below are a few of the hotels we feature as part of our Berkshire holidays. If a hotel you are interested in is not listed, please call us.

Orchards Hotel

View Orchards Hotel

We go above and beyond to make your holiday perfect


Tailor Made for You

  • We tailor make every holiday made around you.
  • Tell us what you'd like to see, what type of accommodation you prefer and how you'd like to travel.
  • We'll plan your perfect holiday, helping you to get the most from your time and budget.


Expert Advice

  • We don't just know travel, we love it!
  • Our Travel Experts have travelled throughout the World. They'll answer your questions with facts not guesses.
  • You'll have a dedicated Travel Expert to look after each stage of your booking.


100% Protected

  • Part of the Stewart Travel group, We've been helping people explore the World for more than 30 years.
  • Every trip is 100% ATOL protected.
  • We're only ever a phone call away.
Make an enquiry