Photo by Caitlin Reese
We found 793 vacation rentals — enter your dates for availability
Discover a selection of 1,000 vacation rentals in The Berkshires, US 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 $90 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.
DynamicDestinationRefinements
AsyncDestinationUrgency
Find the best place to stay — The Berkshires
ReviewsLoader
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy
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, US?
Our 2021 property listings offer a large selection of 793 vacation rentals around The Berkshires. From 575 house rentals to 86 cabin rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.