Where to stay around The Berkshires?

Our 2018 accommodation listings offer a large selection of 924 holiday lettings near The Berkshires. From 536 Houses to 134 Flats, find unique self catering accommodation for you to enjoy a memorable holiday or a weekend with your family and friends. The best place to stay near The Berkshires 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: 15,997 holiday homes
  • Cornwall: 173 holiday homes
  • Vermont: 4,040 holiday homes
  • Connecticut: 1,214 holiday homes
  • New England: 32,992 holiday homes

HomeAway offers you the possibility to discover many other popular destinations in The 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 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 lettings for a perfect city break:

  • Cornwall: 173 holiday lettings
  • Hudson: 363 holiday lettings
  • Great Barrington: 498 holiday lettings
  • Stockbridge: 540 holiday lettings
  • Norfolk: 158 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 The 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 The Berkshires are:

  • Hudson, NY (HCC-Columbia County): 504 self catering accommodations
  • Great Barrington, MA (GBR-Walter J. Koladza): 669 self catering accommodations
  • Pittsfield, MA (PSF-Pittsfield Municipal): 635 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 The Berkshires?

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

  • 62 Center for Theater and Dance: 233 holiday rentals
  • West Cornwall Covered Bridge: 268 holiday rentals
  • Maple Corner Farm Cross Country Ski Area: 237 holiday rentals
  • Lost Acres Vineyard: 107 holiday rentals
  • Hancock Shaker Village: 628 holiday 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 of holiday accommodations.

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.

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)