The Berkshires, Massachusetts
Your Berkshires escape, booked direct.
18 lakefront cabins, ski chalets and homes near Tanglewood, cared for by a local team. Book with us and skip the platform fees.
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Handpicked homes
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Berkshires towns
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Booking fees, ever
“Jaryn was a great, responsive host and we really appreciated the apple cider donuts!”
Meet the founder
Boutique management, rooted in the Berkshires
Jaryn Pierson · Owner / Founder
Berkshire Vacation Rental Co. was built from firsthand experience. While getting our own short-term rentals off the ground, we quickly realized how challenging it was to navigate listings, local markets, and the endless details that come with hosting — without any guidance or support.
That experience became our foundation. Today our local team cares for homes from Lenox to Monterey, and when you book direct, you're booking with us, not a platform.
Rooted in hospitality
We manage every home the way we'd want to arrive at one — warm, ready, and full of the little things that make a place feel like yours.
We've got you covered
Questions before you arrive? Need something during your stay? Our team is located right here in the Berkshires.
Fully stocked homes
Every property is cleaned, stocked, and prepared so your only job is to enjoy the Berkshires.
No booking fees
Book directly with us and skip the platform service fee.
Guest favorites
Homes our guests keep coming back to
Professionally cleaned and inspected before every arrival, and stocked with linens, towels and at least a morning's worth of coffee.
Guest reviews
Stays guests write home about
From 1,684 guest reviews across our homes
For homeowners
Does your property belong in our collection?
The Berkshires are our backyard, and we're excited to share it. We work with homeowners in alignment with our commitment to exceptional experiences.
Be good neighbors.
We manage homes the way we'd want one managed next door to us — quietly, respectfully, and with the whole street in mind.
Tell it straight.
Good news or bad, you'll always hear it from us first — clearly and on time.
Host like a local.
We don't just point guests to the Berkshires, we share the place we love — the trails, the tables, the spots that make a trip worth remembering.
“We live in Europe and they have taken up the challenge of working with us, handling the whole process and keeping us informed all along. The results have shown: since we went live, we have had hardly any empty weekends and the holiday season was fully booked.”
Ready when you are
Your Berkshires getaway starts here.
Choose your home, pick your dates and book directly with our local team, with no booking fees.