Find the best place to stay — The Berkshires

Where to stay around The Berkshires, US?

Our 2018 property listings offer a large selection of 931 vacation rentals near The Berkshires. From 537 houses to 86 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 most popular destinations to visit are:

  • Vermont: 4,233 vacation rentals
  • Connecticut: 1,253 vacation rentals
  • Catskill Mountains: 1,940 vacation rentals
  • New York: 16,546 vacation rentals
  • Hudson Valley: 3,695 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
  • Hudson: 372 rentals
  • Lenox: 354 rentals
  • Wilmington: 407 rentals
  • Stockbridge: 449 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:

  • Bradley International Airport (BDL): 72 vacation rentals
  • Hudson, NY (HCC-Columbia County): 513 vacation rentals
  • Great Barrington, MA (GBR-Walter J. Koladza): 671 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 most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Jiminy Peak: 433 rentals
  • Catamount Ski Area: 692 rentals
  • Talcott Mountain Science Center: 76 rentals
  • Connecticut Valley Winery: 166 rentals
  • Tanglewood Music Center: 702 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.

Head to the captivating city of The Berkshires

Enjoy the area's entertainment, museums and opera and make a vacation rental your home during your stay in The Berkshires. Travelers to this scenic city praise the baseball games, hiking and skiing. A vacation rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in The Berkshires

Are you hoping to discover attractions to see in the city? Travelers enjoy fun activities like hiking and skiing. Venture out of your cozy vacation rental and experience everything that makes The Berkshires a one-of-a-kind vacation spot. These are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Wood's Pond (2.7 mi / 4.3 km)
  • Kennedy Park (3.5 mi / 5.6 km)
  • Pleasant Valley Wilderness Sanctuary (4.7 mi / 7.5 km)
  • Bousquet Ski Area (4.7 mi / 7.5 km)
  • Greenock Country Club (5.5 mi / 8.9 km)
  • Bas Ridge Golf Course (6.4 mi / 10.3 km)

Seasonal weather in The Berkshires

The Berkshires is well known for its skiing. To make the most of the cold weather activities, you might consider visiting in February, March, December or January, when snowfall averages 16.01 inches and temperatures average 14°F.

Exploring the natural features in The Berkshires

Whether you're an active traveler or just want to take in the scenery, The Berkshires is a great place to spend some time outside. Here are some of the area’s noteworthy natural features, all within 30 miles (48.2 km) of the city center:

  • Wood's Pond (2.7 mi / 4.3 km)
  • October Mountain State Forest (3.4 mi / 5.4 km)
  • Kennedy Park (3.5 mi / 5.6 km)
  • Canoe Meadows Wildlife Sanctuary (4.2 mi / 6.8 km)
  • Goose Pond Reservation (6.4 mi / 10.3 km)
  • Berkshire Botanical Garden (8.3 mi / 13.3 km)