Berkshire Vacation Rental Co.

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.

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.

Let's See If We're a Good Fit

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Full Service Management, Personally Delivered

We offer 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

What Our Current Clients are Saying . . .

Jaryn, Donna and all the BVR team have been excellent at setting up and managing our rental property in the Berkshire of Massachusetts. 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. Their fees are reasonable and all expenses are fully justified and transparent. We sincerely appreciate their work and fully recommend them.

Luca N

I've been working with Berkshire Vacation Rental for the past year and they are demonstrating they are the best short term rental management business in The Berkshires. 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

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. He cares deeply about both his clients and their guests, and his attention to detail shows in every interaction. Working with him has given me complete confidence in the care of my property. My recommendation is unhesitating.

Marc S

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

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. He is reliable, communicative, and surrounded by an impressive network of local partners, all of which has been invaluable in maintaining our home in excellent shape throughout the seasons.

Marloes L

Frequently Asked Questions