The Berkshires cottage rentals

Definitely. There are 92 cottage rentals around The Berkshires to pick from. Whether you’re heading to a top city like Great Barrington, Hancock or Lanesborough, our cozy cottages promise a peaceful escape amid gorgeous natural surroundings.

One of the only things better than spending your vacation in a comfortable cottage rental in The Berkshires is getting it for an amazing price. Be on the lookout for any accommodations that offer discounts to guests who book a week. Some properties offer even bigger discounts for month-long stays. You can also make use of Vrbo’s price filter to search for cottages within your budget range.

It depends on what you plan to see and if you’d like to visit in peak, shoulder or low season. May is when most people book a cottage rental in The Berkshires. Average temperatures at this time range between 46ºF (8ºC) and 66ºF (19ºC).

Vrbo makes it easy to find the stunning views you’re looking for in your accommodations. Use the “Location” filter to narrow down the kind of area you prefer to be in, and the views you like to immerse yourself in, while searching cottage rentals in The Berkshires.

For a refreshing escape, it’s tough to beat our lakeside cottage rentals. Use our “Location” filter and then click on “Lake” to see if you can find any comfy properties that’ll put you close to the water in The Berkshires. Spend your days being adventurous or just enjoy watching awesome sunrises and sunsets glittering off the lake.

While you’ll find many exciting things to do in The Berkshires, it comes down to the type of adventure you’re seeking. Once you’ve booked your cottage rental, make a list of activities and attractions that interest you and prioritize them based on your preferences and available time.

No sharing your space, no awkward encounters with strangers. When you book a Vrbo cottage rental, you’ll get the whole place for your use only. Need to cancel or alter your travel itinerary? Our flexible cancellation policies mean you can book your cottage with complete peace of mind. Plus, thanks to our One Key™ rewards program, you’ll be able to earn and redeem 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.