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: 4,382 vacation rentals
  • Connecticut: 1,270 vacation rentals
  • New York: 16,281 vacation rentals
  • Catskill Mountains: 2,058 vacation rentals
  • New England: 36,111 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: 381 rentals
  • Lenox: 355 rentals
  • Pittsfield: 356 rentals
  • Great Barrington: 506 rentals
  • Stockbridge: 457 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): 689 vacation rentals
  • Pittsfield, MA (PSF-Pittsfield Municipal): 616 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: 679 rentals
  • Grafton Lakes State Park: 175 rentals
  • Hotchkiss-Fyler House Museum: 199 rentals
  • Jiminy Peak Mountain Resort: 415 rentals
  • Connecticut Valley Winery: 166 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.