Compare Vacation Rentals & Rent By Owner Homes in Pittsfield, Massachusetts, USA
About Pittsfield Vacation Rentals
With more than 104 Pittsfield vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an RBO property in Pittsfield.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Pittsfield, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (RBOs), and other popular Airbnb-style properties in Pittsfield. Places to stay near Pittsfield are 1168.68 ft² on average, with prices averaging US $378 a night.
RentByOwner makes it easy and safe to find and compare vacation rentals in Pittsfield with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Other Places to Stay in Pittsfield, MA
Pittsfield Vacation Rental Frequently Asked Questions
What are the top vacation rentals in Pittsfield?
- A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything
- Berkshire Lake Beauty-Modern Amenities On The Lake
- Tranquil Lake House Getaway on Onota Lake
- Lake Front Home in Heart of the Berkshires Near Jiminy Peak
- Lakeside Home With Pool-Completely Renovated
- Renovated Pittsfield Colonial by Evergreen Home
- Escape to your cozy retreat near Pontoosuc Lake and Jiminy Peak
- Country Living just minutes from Everything!
- A Private 1940s Elegant Estate, renovated to Modern-Day Luxury - Tanglewood
- Hancock Village Inn at Jiminy Peak
How many Rentbyowner vacation rentals are available in Pittsfield?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 104 in the Pittsfield area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Pittsfield.
