The Berkshires chalet rentals

Definitely. There are 20 chalets around The Berkshires to choose from. Whether you’re heading to a renowned city like Great Barrington, Hancock or Lanesborough, our stays are where comfort meets your next great adventure.

Prices vary depending on the time of year, length of stay and property location, so enter your travel details to check out what’s available in The Berkshires. Whether you’d love a quaint wooden chalet with rustic appeal or a stylish, contemporary one with state-of-the-art features, Vrbo will help you find a retreat to fit your budget.

Think about traveling in May, when the mercury ranges from around 46ºF (8ºC) to 66ºF (19ºC). This is the most popular month to stay in a chalet in The Berkshires.

Use our convenient “Location” filter to find a chalet with the views you’d love to wake up to. Begin by entering the dates you want to book your chalet in The Berkshires, then narrow your options based on the type of area you’d prefer to stay in.

You sure can. If you’re on vacation in a leading city in The Berkshires like Monterey or Lenox, you can look forward to kicking back in a luxe chalet offering perks like large living spaces, top-notch kitchen appliances and a roaring fireplace. Like to unwind without lifting a finger? Browse chalets with wellness centers and other hotel-like perks.

When you simply want to spend your vacation having a blast, not stuck in the kitchen, choose a catered chalet in The Berkshires. The services of professional hosts and chefs are included, so you’ll have all your meals freshly prepared and served each day. All you need to do is unwind and let someone else do the cooking. Of course, the added services mean that these sorts of getaways typically cost a little more.

Venture out and experience all that The Berkshires has to offer from the comfort of your chalet. We recommend doing a little research on the things you’d like to do and see, so you can plan the perfect trip.

Vrbo takes the stress out of arranging your next chalet escape. We’ve got chalets that provide more than the basic hotel room — think private waterfront pads and mountain rental options. Plus, when you join our free One Key™ loyalty program, you’ll earn OneKeyCash™* on eligible bookings on Vrbo, Hotels.com and Expedia. Have a change of plans? Check out our cancellation policies to see if you’re eligible for a 100% refund. *OneKeyCash disclaimer - OneKeyCash is not redeemable for cash and can only be used on Hotels.com, Expedia and Vrbo.