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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

Managing a short-term rental from a distance is tough. We're here in the Berkshires every day — handling guest communications, coordinating cleanings, responding to issues, and making sure your property is always performing at its best.

Our local team handles every detail of your home with care and precision so nothing is left to chance. With hands-on oversight and deep knowledge and love of the Berkshires, we ensure your property is always guest-ready, immaculately maintained, and performing at its highest potential.

We're Your Boots on the Ground

What We Stand For

We manage every home the way we'd want our own managed.

Neighborhood Integrity

We manage every property with the neighborhood in mind — because good neighbors make great communities.

Transparent Messaging

You'll always know what's going on with your property. We communicate openly, honestly, and promptly — even when the news isn't perfect.

Local Ambassadors

Our guests don't just visit the Berkshires — they support it. We actively guide every stay toward authentic local experiences that give back to the community we call home.

Neighborhood Integrity

We manage every property with the neighborhood in mind — because good neighbors make great communities.

Transparent Messaging

You'll always know what's going on with your property. We communicate openly, honestly, and promptly — even when the news isn't perfect.

Local Ambassadors

Our guests don't just visit the Berkshires — they support it. We actively guide every stay toward authentic local experiences that give back to the community we call home.

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.

Get Started — Full Service Management, Personally Delivered

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

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

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

Let's See If We're a Good Fit

Frequently Asked Questions

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.

We work with homeowners who are committed to delivering an exceptional guest experience. If you own a property in the Berkshires — or are looking to invest in one — and you share our passion for quality, hospitality, and neighborhood integrity, we'd love to connect. Not sure if your property is a fit? Reach out and let's find out together.

We keep our pricing simple and transparent. We charge a percentage of your nightly rental rate — no hidden fees, no surprises. Our rate is determined based on the projected performance of your property, ensuring that our success is always tied directly to yours. Reach out to our team to learn more about your specific rate.

Your property is yours — and we want you to enjoy it. Unlike many management companies, we actively encourage our owners to use their homes for personal stays, holidays, and visits with friends and family. Thanks to our owner portal, blocking off dates is simple — log in anytime and reserve your stay with just a few clicks. Whether you're planning months ahead or making a last-minute decision, if the dates are available, they're yours.

The timeline really depends on where you are in the process. If your property is ready to go, we can move quickly — photography, cleaning, and listing setup can all be completed within a couple of weeks. Once we have everything we need on our end, we typically have a listing live within a week. The best way to get a realistic timeline is to reach out and tell us where you're at — we'll take it from there.

Think Your Home Belongs in Our Collection?

Schedule an Intro Call