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 features

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)
How to get there

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.

How many holiday rentals are available around Berkshires?

Our 2020 accommodation listings offer a large selection of 823 holiday lettings around Berkshires. From 94 cabins to 476 houses, find unique self catering accommodation for you to enjoy a memorable stay with your family and friends for a long holiday or a weekend break.

What are the most popular destinations to visit in Berkshires?

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

  • New England: 29,854 holiday homes
  • New York: 17,292 holiday homes
  • Vermont: 3,708 holiday homes
  • Albany: 190 holiday homes
  • Hudson Valley: 3,934 holiday homes offers you the possibility to discover many other popular destinations in Berkshires! Please use our search bar to access the selection of self catering accommodations available in other popular destinations.

What are the main cities to discover in Berkshires?

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

  • Albany: 190 holiday lettings
  • Northampton: 80 holiday lettings
  • Pittsfield: 557 holiday lettings
  • Cheshire: 168 holiday lettings
  • Wilmington: 374 holiday lettings

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 Berkshires?

Yes of course. Our owners offer a large selection of self catering accommodations near to airports. Airports with a large selection of self catering accommodations in Berkshires are:

  • Great Barrington, MA (GBR-Walter J. Koladza): 544 self catering accommodations
  • Barnes Municipal Airport (BAF): 109 self catering accommodations
  • Bradley International Airport (BDL): 94 self catering accommodations

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

What are the most popular points of interest and landmarks to stay near in Berkshires? offers a large selection of holiday lettings near great places to visit in Berkshires. From travellers, the top popular points of interest to stay for a holiday trip or just for a weekend are:

  • Jiminy Peak Mountain Resort: 319 holiday rentals
  • Mark Twain House Museum: 139 holiday rentals
  • Norfolk Historical Museum: 295 holiday rentals
  • West Cornwall Covered Bridge: 259 holiday rentals
  • New York State Executive Mansion: 159 holiday rentals

But there are many other points of interest around Berkshires listed on where you can find your place to stay. Just write your wanted destination in our search bar and have a look at our selection of holiday accommodations.