Compare Vacation Rentals & Rent By Owner Homes in The Berkshires, Massachusetts, USA
About The Berkshires Vacation Rentals
With more than 1624 The Berkshires 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 The Berkshires.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner The Berkshires, 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 The Berkshires. Places to stay near The Berkshires are 1052.35 ft² on average, with prices averaging CA $616 a night.
RentByOwner makes it easy and safe to find and compare vacation rentals in The Berkshires 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 The Berkshires, MA
Frequently Asked Questions About The Berkshires?
What are the top vacation rentals in The Berkshires?
- Swiss Chalet Style Timber frame Home In Berkshires With All Modern Conveniences
- “Elterwater”-Swan lake. Your own lakefront oasis, a true Berkshire getaway
- 4Br/3bath Lakefront/Ski House in Berkshires. Hi speed wifi
- Unique Condo, Quiet Neighborhood, Walk to Town.
- Huge Luxe Williamstown Updated Victorian, All Ensuite Baths, Walk to Spring St!
- Location! Location! Berkshire Glamour (and comfort) Meets Town And Country
- Devonfield Inn B&B
- A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything
- An Elegant Time Capsule in Downtown Lenox
- Cozy Monterey Family Chalet, Minutes From Lake & 10 Minutes From Butternut!
How many Rentbyowner vacation rentals are available in The Berkshires?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 1624 in the The Berkshires 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 The Berkshires.
Nearby Neighborhood (1)
| Neighborhood | Property Count |
|---|---|
| Sherwood Forest Vacation Rentals in Massachusetts | 69 |
