Enjoy a personalized, caring approach to property management that keeps your home charming and profitable.

Experience Effortless Hosting

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.

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

Sleeps 12 | 4 Bedrooms | 7 Beds | 4 Bathrooms

Discover Hilltop Hideaway

Your Home Away from Home in the Berkshires

Nestled atop a serene hillside in Southfield, MA on 100 acres, Hilltop Hideaway offers breathtaking views, modern amenities, and the perfect blend of comfort and style. This charming guest house is ideal for family vacations, romantic getaways, or relaxing escapes with friends.

Enjoy an outdoor oasis with a spacious deck, fire pit, and hot tub. Inside, find a fully equipped kitchen, a cozy gas fireplace, and fast Wi-Fi. Just 25 minutes from Great Barrington, scenic hikes, and local dining, this retreat offers comfort and convenience in a prime location.

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