Destination guide

Head to the captivating city of The Berkshires

Enjoy the area's entertainment, museums and opera with a rental holiday home in The Berkshires. Travellers to this scenic city praise the baseball games, hiking and skiing. A holiday 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? Travellers enjoy fun activities like hiking and skiing. Venture out of your cosy holiday rental and experience everything that makes The Berkshires a one-of-a-kind holiday spot. These are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • 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 40.68 inches and temperatures average -10°F.

Natural highlights

Exploring the natural features in The Berkshires

Whether you're an active traveller 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 centre:

  • 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)

Transport options to and around The Berkshires

Fly into Pittsfield, MA (PSF-Pittsfield Municipal), the closest airport, located 5.5 mi (8.9 km) from the city centre. If you're unable to find a flight that fits your schedule, you can also fly into Hudson, NY (HCC-Columbia County), which is 26.3 mi (42.4 km) away.

If you'd rather travel by train, make your way to Pittsfield Station or Pittsfield Intermodal Transportation Center to see more of the city.

Where to stay near The Berkshires?

Our 2019 accommodation listings offer a large selection of 992 holiday rentals near The Berkshires. From 580 Houses to 124 Cabins, find unique holiday homes for you to enjoy a memorable stay with your family and friends. The best place to stay near The Berkshires for a long holiday or a weekend break is on HomeAway.

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

There are many lovely places to stay for a long holiday or just a weekend break in The Berkshires. From HomeAway travellers, the popular destinations to visit are:

  • New York: 16,770 holiday rentals
  • Vermont: 4,326 holiday rentals
  • Wilmington: 436 holiday rentals
  • Great Barrington: 526 holiday rentals
  • New England: 36,986 holiday rentals

HomeAway offers you the possibility to discover many other popular destinations in The Berkshires! Please use our search bar to access the selection of holiday rentals available in other popular destinations.

What are the main cities to discover in The Berkshires?

Whether you are travelling solo or with family and friends, here are the cities in The Berkshires with the largest selection of holiday rentals for a perfect city break:

  • Wilmington: 436 holiday homes
  • Great Barrington: 526 holiday homes
  • Hudson: 386 holiday homes
  • Brattleboro: 683 holiday homes
  • Litchfield: 160 holiday homes

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

Can I find easy access holiday homes when travelling by plane to The Berkshires?

Yes of course. Our owners offer a large selection of holiday homes near to airports. Airports with a large selection of rentals in The Berkshires are:

  • Bradley International Airport (BDL): 90 holiday houses
  • Hudson, NY (HCC-Columbia County): 532 holiday houses
  • Barnes Municipal Airport (BAF): 121 holiday houses

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