Discover a selection of 1,000 vacation rentals in The Berkshires that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $135 per night, and houses and cabins are popular options for a stay in The Berkshires. Either way, you'll find a rental for everyone's needs.
AsyncDestinationUrgency
Top rated rentals — The Berkshires
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy
Destination guide

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

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)
Weather

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.

Natural features

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)
How to get there

Transportation 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 center. 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 vacation rentals are available around The Berkshires?

Our 2021 property listings offer a large selection of 811 vacation rentals around The Berkshires. From 595 house rentals to 98 cabin rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.