Escape from New York

5 vacation rentals in the Berkshires that are still available this summer

By Austin Havens-Bowen  |
July 22, 2022 - 9:30AM

This Stockbridge three bedroom has availability in August for $559 a night. 


If you’re looking for a place to take a last-minute summer vacation and aren’t a fan of the beach, check out the Berkshires—the mountainous Massachusetts region known for its history, quaint towns, and year-round outdoor activities. 

To enjoy the great outdoors in the summer, you can hike the area’s many trails like Basin Pond in Becket and Alford Springs in Great Barrington; enjoy the waterfalls at Umpachene Falls Park; take a swim at Pontoosuc Lake or Lenox Town Beach; and visit High Lawn Farm in Lee. There’s also lots for outdoorsy types to do at Balance Rock State Park.

For a bit of culture, you can check out museums like Norman Rockwell Museum, Berkshire Museum, and Clark Art Institute or catch a performance at Tanglewood or The Colonial Theater. Great Barrington and Stockbridge also have popular downtown areas where you can shop and dine at independently-owned spots.

To help with your last-minute vacation, here are five rentals with availability this summer in the Berkshires. (And remember to pay attention to pet policies, rules about large gatherings, check-in times, and extra cleaning fees.)  

Pittsfield one bedroom

This one bedroom, one bath is available in August for $275 a night. The historic schoolhouse sleeps up to four people and pets are allowed. It has a loft, ceiling fans, pond, deck, fire pit, grill, hammock, and a washer/dryer. Berkshire County Historical Society and Colonial Theater are nearby. 

Sheffield three bedroom 

This three bedroom, two and a half bath is available in July and August for $326 a night. The house sleeps up to 10 people and pets are not allowed. It has a movie room, covered porch, patio, large yard, and central air with Nest controls. Umpachene Falls Park is nearby. 

Great Barrington three bedroom  

This three bedroom, one bath is available in mid-August for $555 a night. It sleeps up to eight people and pets are welcome with a $100 fee for pets below 25 pounds and $200 for bigger pets. The house features mountain views, a decorative fireplace, patio, deck, fire pit, central heat, window air conditioning, a grill, and washer/dryer. Tanglewood is nearby. 

Stockbridge three bedroom

This three bedroom, one and a half bath is available at the end of August for $559 a night. It sleeps six and up to three pets are allowed with a fee. The house has a fireplace, 114 acres of land and hiking trails, a grill, deck, central air, and parking for four cars. The Norman Rockwell Museum is nearby. 

Lenox two bedroom 

This two bedroom, two bath is available in August for $877 a night. The house sleeps six people and pets are not allowed. It has oversized windows, central air and heat, a smart TV, and a washer/dryer. Lenox Library and Shakespeare & Company are nearby. 



Austin Havens-Bowen

Staff Writer

Staff writer Austin Havens-Bowen covers the rental market and answers renters' questions in a column called Realty Bites. He previously reported on local news for the Queens Ledger and The Hunts Point Express in the Bronx. He graduated from Hunter College with a BA in media studies. He rents a one-bedroom apartment in Astoria with his boyfriend and their two cats.

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