Where to stay around The Berkshires?

Our 2018 accommodation listings offer a large selection of 891 holiday lettings near The Berkshires. From 525 houses to 89 cottages, 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: 16,263 holiday homes
  • Cornwall: 173 holiday homes
  • Vermont: 3,953 holiday homes
  • Connecticut: 1,260 holiday homes
  • New England: 33,734 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
  • Great Barrington: 496 holiday lettings
  • Hudson: 373 holiday lettings
  • Stockbridge: 444 holiday lettings
  • Norfolk: 156 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): 509 self catering accommodations
  • Great Barrington, MA (GBR-Walter J. Koladza): 666 self catering accommodations
  • Pittsfield, MA (PSF-Pittsfield Municipal): 595 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: 195 holiday rentals
  • West Cornwall Covered Bridge: 274 holiday rentals
  • Maple Corner Farm Cross Country Ski Area: 225 holiday rentals
  • Lost Acres Vineyard: 105 holiday rentals
  • Hancock Shaker Village: 587 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.

The captivating area of The Berkshires awaits your stay

Take a holiday to The Berkshires and enjoy the area's entertainment, opera and museums. Revered for its hiking, skiing and baseball, this city is both scenic and university. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Attractions in and around The Berkshires

First time in The Berkshires and looking for places to see? Don't miss cultural highlights such as Bidwell House Museum, Jacob's Pillow and Animagic Museum of Animation. If some outdoor time is on the agenda, experience the natural beauty of Tolland State Forest, Tyringham Cobble and Umpachene Falls Park. Winter enthusiasts will find Otis Ridge, Ski Butternut and Catamount Ski Area in the city. Also while in town, you can visit Beartown State Forest, Goose Pond Reservation or Mahaiwe Performing Arts Center.