The Berkshires, MA, USA

The Berkshires, MA, USA

We found 900 vacation rentals — enter your dates for availability

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Find the best place to stay — The Berkshires

Where to stay around The Berkshires, US?

Our 2018 property listings offer a large selection of 900 vacation rentals near The Berkshires. From 513 houses to 85 cottages, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near The Berkshires for a holiday or a weekend are on VRBO.

What are the most popular destinations to visit in The Berkshires?

There are many lovely places to stay for a holiday trip or just for a weekend in The Berkshires. From VRBO travelers, the top 5 most popular destinations to visit are:

  • Catskill Mountains: 2,015 vacation rentals
  • Vermont: 4,358 vacation rentals
  • Great Barrington: 497 vacation rentals
  • Lenox: 360 vacation rentals
  • New York: 15,963 vacation rentals

And VRBO offers you the chance to discover many other popular destinations in The Berkshires! Please use our search bar to access the selection of vacation rentals available in other popular destinations.

What are the main cities to discover in The Berkshires?

Whether you're traveling with family or friends, here are the cities with the largest selection of vacation rentals for a holiday trip or just for a weekend in The Berkshires:

  • Great Barrington: 497 rentals
  • Lenox: 360 rentals
  • Lee: 481 rentals
  • Stockbridge: 454 rentals
  • Wilmington: 409 rentals

For other cities, please use our search bar to access the selection of vacation rentals available.

Can I find easy-access vacation rentals when traveling by plane to The Berkshires?

Yes of course. Our owners offer a large selection of vacation rentals near airports. The airports with a large selection of vacation rentals in The Berkshires are:

  • Hudson, NY (HCC-Columbia County): 502 vacation rentals
  • Great Barrington, MA (GBR-Walter J. Koladza): 676 vacation rentals
  • Pittsfield, MA (PSF-Pittsfield Municipal): 614 vacation rentals

For other airports, please use our search bar to access the selection of vacation rentals available.

Near which points of interest can I spend my holidays in The Berkshires?

VRBO offers a large selection of rentals near lovely places in The Berkshires. From VRBO travelers, the top 5 most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Tanglewood Music Center: 683 rentals
  • Connecticut Valley Winery: 162 rentals
  • Jiminy Peak Mountain Resort: 417 rentals
  • 62 Center for Theater and Dance: 208 rentals
  • Look Memorial Park: 90 rentals

But there are many other points of interest around The Berkshires listed on VRBO where you can find your place to stay. Just write your wanted destination in our search bar and have a look at our selection.

The Captivating Area of The Berkshires Awaits Your Stay

Take a vacation to The Berkshires and enjoy the area's entertainment, opera and museums. Revered for its hiking, skiing and baseball, this city is both scenic and student-friendly. With a vacation rental, you get a home away from home—many rentals offer full kitchens and outdoor grills for some home cooking.

Attractions In and Around The Berkshires

First time in The Berkshires and looking for places to see? Don't miss cultural highlights like Bidwell House Museum, Jacob's Pillow and Animagic Museum of Animation. If some outdoor time is on the agenda, experience the natural beauty of Tolland State Forest, Tyringham Cobble and Umpachene Falls Park. Winter enthusiasts will find Otis Ridge, Ski Butternut and Catamount Ski Area in the city. Also while in town, you can visit Beartown State Forest, Goose Pond Reservation or Mahaiwe Performing Arts Center.