Search Results - Vacation Rentals

Great Barrington, Massachusetts Vacation Rentals

5 listings found
About Great Barrington, Massachusetts

“You can get anything you want at Alice’s Restaurant”.  If you are a child of the Greatest Generation, the Boomers as we are called, you recognize this lyric written by Arlo Guthrie back on Thanksgiving Day, 1965. It’s called the “Alice’s Restaurant Massacree” and Mr. Guthrie relates in an 18 minute soliloquy about his run in with the law over illegal trash dumping. This incident occurred in Great Barrington Massachusetts and started a career for Mr. Guthrie that has been long and entertaining.

As you might imagine, Alice’s Restaurant isn’t around anymore. But, as the song says, “Alice didn’t live in a restaurant. She lived in the church nearby the restaurant…” And the old Trinity Church, where Alice once lived and where the saga began has become home to The Guthrie Center and The Guthrie Foundation.  Today Great Barrington is a popular tourist destination because this song is part of a past filled with memories of a tumultuous and yet wonderful time.

Many towns have some sort of “claim to fame” and Mr. Guthrie has given Great Barrington one. However, there is much more to offer in this quaint town and the surrounding areas.  In 2012, Smithsonian magazine ranked Great Barrington #1 in its list of "The 20 Best Small Towns in America", and once you visit, it’s obvious why you would choose this place to vacation.

Great Barrington is a vibrant small town with a permanent population of around 2,200 but it also has many second homes that are owned by Bostonians and New Yorkers. Because it has become a vacation destination, Great Barrington is home to over 55 restaurants ranging from drive ins to fine dining.

The Appalachian Trail passes nearby as it winds through the scenic network of mountains, streams, lakes and forests. In addition vacationers can experience the eclectic retail shops, exquisite art galleries as well as antique stores filled with keepsakes; all located in the downtown area. By the way, most of these shops are locally owned which guarantees personal attention from the merchants.  If you enjoy world-class performing arts, the recently renovated Mahaiwe Theater has become a center for year-round music and cultural events.

Great Barrington needs to be on your bucket list of places to go on vacation. There’s is plenty to do whether you enjoy strenuous activity or leisurely strolls. Come see us and experience the ultimate vacation destination.

LEARN MORESHOW LESS
Rate & Availability Disclaimer
Base rates (EXCLUDING any applicable taxes, fees, and promotions) are displayed as provided by rental managers and are not guaranteed. Rates are based on the start date or arrival date selected in the search and may vary on subsequent days. Properties marked ‘Available’ or ‘Booked’ are done so based on information provided by the rental manager and are not guaranteed. For completed details (including minimum stay length, full availability information, approved arrival days and other booking rules for the property) select ‘Book Now” (on available properties) or ‘Check Availability’ (booked properties) to be directed to the rental manager’s website or click “Contact” to send them a specific request.