Property management
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.
Rather talk? Call Jaryn at (413) 429-9558- Homes we care for
- 18
- Average guest rating
- 4.88★
- In-house cleaning team
- Local
Homes we care for
Average guest rating
In-house cleaning team
Who we are
We're your boots on the ground
We're a Berkshires-born vacation rental company built on the belief that this place deserves great hosts. We take care of the homes we manage like they're our own, look out for the neighborhoods they sit in, and treat every guest like we'd treat a friend coming up for the weekend.
What we stand for: we manage every home the way we'd want our own managed.
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.
What we handle
Full-service management, personally delivered
A complete suite of management services, delivered with the personal touch that only a boutique, locally rooted company can provide.
Curated professional photography
Photography that sells the experience, not just the space.
White-glove listing build-out
Your listing built, optimized and ready to book.
Proper pricing
Revenue management tailored to your property and your goals.
Owner reporting
Monthly owner statements, delivered with full transparency.
Listing turnover
Professional turnovers handled by our own in-house cleaning team.
Guest supply restocks
Curated amenity restocks managed monthly on your behalf.
How it works
From first call to first booking
Start with a conversation
We get to know you, your property and your goals.
Onboarding, step by step
We walk you through setup so everything is right from day one.
Photos, cleaning & listing
Photography, cleaning and listing setup within a couple of weeks.
Go live
Once we have everything we need, your listing is typically live within a week.
From our homeowners
“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.”
Luca N.
Homeowner
“They have outstanding communications and follow-ups. No issue or question has ever been dropped. Jaryn and the whole bunch of great people behind the scenes help make this whole relationship work.”
Brent S. · Homeowner
“Berkshire Vacation Rental has been an outstanding partner in managing my cottage in Stockbridge. Jaryn Pierson is a true professional—attentive, thoughtful, and consistently responsive. My recommendation is unhesitating.”
Marc S. · Homeowner
“Jaryn and his team at Berkshire vacation rentals are professional, extremely responsive and run a very sophisticated property management and property rental program. Well Done.”
Gary S. · Homeowner
“From the very beginning, Jaryn has gone above and beyond to ensure our Airbnb consistently meets and exceeds guest expectations—offering thoughtful advice on everything from practical essentials to subtle aesthetic touches.”
Marloes L. · Homeowner
Owner FAQ
Questions from homeowners
Prefer to talk it through? Reach Jaryn Pierson and the team directly.
We start with a conversation — getting to know you, your property, and your goals. From there we'll walk you through our onboarding process step by step, making sure everything is set up right from day one. Short-term rental management can be complex, but that's exactly why we're here.
Let's see if we're a good fit.
No commitment. Tell us about your home and we'll be in touch.