Enjoy a personalized, caring approach to property management that keeps your home charming and profitable.
Jessie’s Services
Jessie’s Services is a property management company specializing in short-term vacation rentals. We offer an all-in-one solution for homeowners, managing everything from guest communication and concierge services to cleaning and maintenance. Our goal is to provide a worry-free experience for property owners while delivering exceptional stays for renters.
Experience Effortless Hosting
Hassle-Free Management, Maximized Returns
We take care of every detail, from guest communication to property upkeep, so you can focus on what matters most- without the stress of managing a rental
Professional Listing & Dynamic Pricing
Guest Communication & Support
Housekeeping & Maintenance Coordination
Compliance & Financial Management
Discover Your Next Berkshire Getaway
Sleeps 12 | 5 Bedrooms | 7 beds | 4 Bathrooms
Hilltop Serenity
Outdoor Oasis
Expansive deck with seating, a fire pit, and stunning vistas.
Thoughtful Amenities
Fully equipped kitchen, cozy fireplaces, and high-speed Wi-Fi.
Prime Location
Short drive to Great Barrington, hiking trails, and local dining.
Sleeps 14 | 6 Bedrooms | 11 beds | 6.5 Bathrooms
Sunset Falls
Luxurious Mountain Retreat
Modern architecture, floor-to-ceiling windows, and breathtaking mountain views.
Spa & Wellness
Hot tub, steam room, radiant heated floors, and in-house massage services.
Entertainment & Recreation
Game room, gym, pool table, foosball, hiking trails, and concierge services.
Who we are
At Jessie’s Services, we blend exceptional hospitality with expert property management, led by our founder, Jessica Holcomb. With over 20 years of experience, Jessica’s “people-first” approach and relentless attention to detail ensure memorable guest experiences and outstanding results for property owners in Berkshire County. Learn more