Where to stay around The Berkshires?

Our 2018 property listings offer a large selection of 946 vacation rentals near The Berkshires. From 528 Houses to 142 Condos/Apartments, 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 HomeAway.

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 HomeAway travelers, the most popular destinations to visit are:

  • Vermont: 4,521 vacation rentals
  • Connecticut: 1,952 vacation rentals
  • New York: 20,862 vacation rentals
  • Catskill Mountains: 1,935 vacation rentals
  • Hudson Valley: 4,614 vacation rentals

And HomeAway 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:

  • Stratton: 787 rentals
  • Hudson: 365 rentals
  • Lenox: 356 rentals
  • Great Barrington: 501 rentals
  • Stockbridge: 544 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): 101 vacation rentals
  • Great Barrington, MA (GBR-Walter J. Koladza): 667 vacation rentals
  • Hudson, NY (HCC-Columbia County): 503 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?

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

  • Jiminy Peak Mountain Resort: 408 rentals
  • Ski Butternut: 554 rentals
  • Western Gateway Heritage State Park: 343 rentals
  • Connecticut Valley Winery: 184 rentals
  • Tanglewood Music Center: 615 rentals

But there are many other points of interest around The Berkshires listed on HomeAway 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)