Where to stay around Berkshire County?

Our 2019 accommodation listings offer a large selection of 666 holiday lettings near Berkshire County. From 377 Houses to 129 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 Berkshire County is on HomeAway.

What are the most popular destinations to visit in Berkshire County?

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

  • Great Barrington: 506 holiday homes
  • Pittsfield: 699 holiday homes
  • Stockbridge: 550 holiday homes
  • Lenox: 363 holiday homes
  • Tyringham: 494 holiday homes

HomeAway offers you the possibility to discover many other popular destinations in Berkshire County! 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 Berkshire County?

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

  • Great Barrington: 506 holiday lettings
  • Pittsfield: 699 holiday lettings
  • Stockbridge: 550 holiday lettings
  • Lenox: 363 holiday lettings
  • Tyringham: 494 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 Berkshire County?

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 Berkshire County are:

  • Great Barrington, MA (GBR-Walter J. Koladza): 674 self catering accommodations
  • Pittsfield, MA (PSF-Pittsfield Municipal): 657 self catering accommodations
  • Hudson, NY (HCC-Columbia County): 510 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 Berkshire County?

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

  • Tanglewood Music Center: 628 holiday rentals
  • Berkshire Theatre Festival: 746 holiday rentals
  • 62 Center for Theater and Dance: 243 holiday rentals
  • Ski Butternut: 562 holiday rentals
  • Cranwell Golf Club: 710 holiday rentals

But there are many other points of interest around Berkshire County 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.

Make a vacation rental in Berkshires, USA your home away from home

The Berkshires are a range of hills in Northwestern Massachusetts. Holidaymakers head for vacation rentals in the Berkshires to admire some lovely natural landscapes and take part if a host of outdoor activities, from walking to mountain biking and horseback riding. The region is also a key centre for the arts, with various important institutions located here.

Things to do in the Berkshires, USA

The region around Berkshires vacation accommodation is first and foremost a destination for outdoor activities. The world-famous Appalachian Trail runs through here, and there is also a huge network of other trails to explore taking walkers through expanses rich in natural beauty. A highlight is Mount Washington, a pretty town with easy access to the eponymous State Park. Nearby Bash Bish Falls, the highest waterfall in the state is found in this area.

In summer around Berkshire accommodation you could make the most of the region’s rivers, going on a fishing or rafting trip. On land you could head for one of the area’s many excellent golf courses. Great choices would be Berkshire Hills Country Club, Pontoosuc Lake, Wahconah, Bas Ridge, Skyline, Waubeeka, Taconic and Donnybrook.

Meanwhile in the winter, Berkshire vacation rentals are found in a good winter sport destination. Perhaps the most popular activity at this time of year is cross-country skiing, thanks to the numerous national parks, but there are also a number of resorts here, including Catamount, Bousquet and Jiminy Peak, which is the largest resort for ski and snowboard in the whole of New England.

Places to visit on holiday in Berkshires, USA

The City of Albany, in Upstate New York, is no more than an hour by car from Berkshires self-catering accommodation. It’s the capital of the state. And features New York’s Capitol with its elaborate architecture, as well as the Empire State Plaza, which is a venue for live music in the summer months. The New York State Museum is the largest of its kind in the country, and details the history of the state.

Weather in Berkshires, USA

On holiday at Berkshires vacation rentals you’ll be able to expect cold weather in winter, with temperatures slipping below freezing between November and March. There’s also quite a lot of snowfall on higher ground at this time of year. In summer there are warm conditions, from June to September.

Cheap flights to Berkshires, USA

If you head for Berkshires self-catering vacation accommodation from the UK, the most convenient way to get here would be to fly to Boston Logan International (BOS) from London Heathrow (LHR) with Delta, Virgin or British Airways, and then make the two hour drive across to Berkshire County.

Explore destinations around Berkshire County