Berkshire County cottage rentals

Pick from 82 cottage rentals in Berkshire County. Take the family on a memorable adventure to Great Barrington or visit other cities like Hancock and Lanesborough. Wherever you plan to go, our cottages present the chance to switch off the phone and enjoy a rejuvenating retreat without unwanted distractions.

Prices vary depending on the time of year, length of stay and exact property location, so enter your travel details to browse what’s available. Whatever your style or budget, Vrbo has cottage rentals in Berkshire County for every kind of guest.

Many guests love to experience the coziness, charm and privacy of a Berkshire County cottage rental in May. If you want to visit this captivating destination then, give yourself a head start by booking as far in advance as possible. This can help you lock in the perfect cottage in your preferred surroundings. You may also come across options featuring early bird discounts.

Use our convenient “Location” filter to find a cottage rental with the views you dream of waking up to. Begin by entering the dates you want to book your cottage in Berkshire County, then narrow your search based on the sort of area you’d rather stay in.

Stunning views of sparkling water, the wonder of nature and outdoor activities are a few of the things to enjoy in one of Vrbo’s lakeside cottage rentals. Use our handy “Location” filter and check the “Lake” box to find out if there are any cozy stays in Berkshire County by the water.

While you’ll find plenty ofs awesome things to do in Berkshire County, it comes down to the kind of adventure you’re looking for. Once you’ve locked in your cottage rental, make a list of attractions or activities you’re interested in and prioritize them based on your preferences, travel companions and trip length.

No sharing your space, no awkward encounters with strangers. When you stay in a Vrbo cottage rental, you’ll get the whole place to yourself. Need to cancel or change your itinerary? Our flexible cancellation policies let you book your cottage with total peace of mind. Plus, thanks to our One Key™ loyalty program, you’ll be able to earn and use OneKeyCash™* on all eligible bookings on Vrbo, Hotels.com and Expedia. *OneKeyCash disclaimer - OneKeyCash is not redeemable for cash and can only be used on Vrbo, Expedia and Hotels.com.