Find the best place to stay — The Berkshires

Where to stay around The Berkshires?

Our 2018 property listings offer a large selection of 896 vacation rentals near The Berkshires. From 519 houses to 87 cottages, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near The Berkshires for a holiday or a weekend are on HomeAway.

What are the most popular destinations to visit in The Berkshires?

There are many lovely places to stay for a holiday trip or just for a weekend in The Berkshires. From HomeAway travelers, the most popular destinations to visit are:

  • Vermont: 4,273 vacation rentals
  • Connecticut: 1,331 vacation rentals
  • New York: 16,875 vacation rentals
  • Catskill Mountains: 2,098 vacation rentals
  • Hudson Valley: 3,785 vacation rentals

And HomeAway offers you the chance to discover many other popular destinations in The Berkshires! Please use our search bar to access the selection of vacation rentals available in other popular destinations.

What are the main cities to discover in The Berkshires?

Whether you're traveling with family or friends, here are the cities with the largest selection of vacation rentals for a holiday trip or just for a weekend in The Berkshires:

  • Stratton: 783 rentals
  • Hudson: 379 rentals
  • Lenox: 356 rentals
  • Great Barrington: 503 rentals
  • Stockbridge: 451 rentals

For other cities, please use our search bar to access the selection of vacation rentals available.

Can I find easy-access vacation rentals when traveling by plane to The Berkshires?

Yes of course. Our owners offer a large selection of vacation rentals near airports. The airports with a large selection of vacation rentals in The Berkshires are:

  • Bradley International Airport (BDL): 72 vacation rentals
  • Columbia County Airport (HCC): 512 vacation rentals
  • Great Barrington, MA (GBR-Walter J. Koladza): 679 vacation rentals

For other airports, please use our search bar to access the selection of vacation rentals available.

Near which points of interest can I spend my holidays in The Berkshires?

HomeAway offers a large selection of rentals near lovely places in The Berkshires. From HomeAway travelers, the most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Jiminy Peak Mountain Resort: 405 rentals
  • Ski Butternut: 670 rentals
  • Western Gateway Heritage State Park: 300 rentals
  • Connecticut Valley Winery: 166 rentals
  • Tanglewood Music Center: 675 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.

The Captivating Area of The Berkshires Awaits Your Stay

Take a vacation 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 student-friendly. With a vacation 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 like 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.