The Berkshires, MA, USA

The Berkshires, MA, USA

We found 905 vacation rentals — enter your dates for availability

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Find the best place to stay — The Berkshires

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:

  • Vermont: 4,378 vacation rentals
  • Connecticut: 1,265 vacation rentals
  • New York: 16,234 vacation rentals
  • Catskill Mountains: 2,041 vacation rentals
  • New England: 36,070 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:

  • Hudson: 383 rentals
  • Pittsfield: 358 rentals
  • Stockbridge: 460 rentals
  • Lenox: 359 rentals
  • Northampton: 52 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): 512 vacation rentals
  • Great Barrington, MA (GBR-Walter J. Koladza): 690 vacation rentals
  • Pittsfield, MA (PSF-Pittsfield Municipal): 615 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
  • Grafton Lakes State Park: 176 rentals
  • Hotchkiss-Fyler House Museum: 200 rentals
  • Jiminy Peak Mountain Resort: 416 rentals
  • Mount Snow Golf Course: 763 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.