Pittsfield villa rentals

A number of factors will determine the price of a villa rental in Pittsfield, such as property size and how long and when you’re traveling. All you have to do is key in your travel dates and preferences to find a villa that meets your budget and style.

The best time to visit Pittsfield depends on factors like activities that you want to do and your preferred season. With average temperatures of between 59ºF (15ºC) and 80ºF (27ºC), July is a popular month to get a villa rental in this corner of The Berkshires. Want to really experience the culture and vibe of this destination? Check for any local festivals or events and organize your villa rental around them.

Toss in views of historic areas on top of your fantastic villa rental and you’ve got yourself the recipe for a truly unforgettable Pittsfield trip. Some of our highly sought-after villas in this destination boast these types of outlooks. Browse for others by using our “Location” filter.

Book an upscale villa rental in Pittsfield and vacation like a celebrity. These stays often include plush furnishings and technology features like whole-home surround sound systems. Look for villas with a swimming pool and hot tub, or with a secluded patio perfect for sunbathing. With plenty of room to spread out, they’re perfect for vacations with the whole family, reunions or group trips.

With attractions like Tanglewood Music Center, Jiminy Peak Mountain Resort and National Shrine of the Divine Mercy, you’ll have no trouble discovering fun things for your whole crew to do together during your Pittsfield break. You’ll also need a cozy place to retreat to in between your sightseeing adventures. That’s where we come in. We have a range of villa rentals here will all the essentials for an enjoyable and comfortable getaway.

No sharing your space, no awkward experiences with strangers. When you stay in a Vrbo villa rental, you’ll get the whole place to yourself. And with our free rewards program, One Key™, you can collect OneKeyCash™* on eligible bookings on Vrbo, Expedia and Hotels.com. Need to alter or cancel your plans? Our flexible cancellation policies mean you’re able to book your villa with peace of mind. *OneKeyCash disclaimer - OneKeyCash is not redeemable for cash and can only be used on Vrbo, Expedia and Hotels.com.