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Boutique Vacation Stays & Stress-Free Rental Management in Virginia

Proudly Serving Richmond, Charlottesville, Harrisonburg, & the Shenandoah Valley

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Where Comfort Meets Care

At Pathway Properties, we offer curated vacation rentals in Virginia and boutique short-term rental management for homeowners. Whether you’re booking a scenic escape or looking for expert Airbnb hosting, we make every step simple and stress-free.

Featured Expertly-Curated Properties

Escape to the mountains, sip wine by the fire, and unwind in a handpicked stay.

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  • ★★★★★

    "I stayed here for my 30th birthday with 14 friends and it was incredible! Everyone had a comfortable and beautiful bed. The hot tub was wonderful there were so many gorgeous places to gather as a group which was so helpful. We had an amazing time, the views were gorgeous and the house manager Holly was SO helpful. Thank you so much for this amazing stay!"

    — Becky, Love Afton Cabin

  • ★★★★★

    "Holly was a fantastic host, and the home was comfortable, clean, and perfectly situated. The home had wonderful amenities (especially for parents of a toddler) and was very close to a number of wineries and breweries. A great stay and highly recommend!"

    — Krystal, Time to Wine Down

  • ★★★★★

    "Great location! Loved the fire pit area on the property! Plenty of space for a family and kid friendly! Plenty of books and an air hockey table! Everything was neat and clean and holly was extremely responsive and friendly! Overall, a great find!"

    — Kayla, Time to Wine Down

  • ★★★★★

    "This house was so inviting, comfortable, and perfect for our group. Everything was exactly as described, the beds were comfortable, and the hot tub was wonderful. The host was amazing to work with and very quick to respond to any questions." 

    - Lynn, Wintergreen Ridge Retreat

  • ★★★★★

    "Our experience was terrific! Holly was super responsive and absolutely proactive in getting the hottub repaired during our stay. The house was awesome and very well-stocked with basic supplies and cooking utensils. We would love to come back to this location and I hope that Holly is the one that we deal with again!

    — Brandon, Adventure Awaits 

  • ★★★★★

    "We came to the area for my bachelorette. The AirBnb was perfect. All 8 of us had our own bed. We enjoyed the location and its proximity to local wineries & downtown Charlottesville. Everyone enjoyed their stay! We had plenty of downtime and also enjoyed charcuterie and s’mores at the Airbnb. We also had a permanent jewelry vendor come do a pop up for us at the house! Those were some of the highlights! Emily, Holly, & team were responsive & provided clear instructions. Would definitely come again or check out their other properties in the area!"

    — Katie, Fern Cottage 

  • ★★★★★

    "What a marvelous setting. This house was exquisite and the host was friendly and responsive. We couldn’t have asked for anything more. We enjoyed morning coffee sitting in the screened in porch. And then sitting outside on the deck watching the super moon rise over the mountains. Every member of the group commented on how well they slept and how comfy the beds were. I would definitely return here."

    — Douglas, Love Afton Cabin 

  • ★★★★★

    "My husband, toddler and I decided to get away before our baby comes in March, and this was the perfect spot. The views were breathtaking and we were lucky enough to experience the place in the snow. The access road and the driveway were still easily navigable in our Sorento. The town of Goshen is quaint and beautiful, perfect for a getaway from hustle and bustle. The house was equipped with literally everything you could need for your stay- it’s very obvious that the hosts put a lot of thought into their guest experience. The house itself is beautiful, wonderfully maintained and spacious. Overall, this was one of our favorite stays we’ve been on and look forward to booking again."

    — Amanda, Shenandoah Retreat 

Stress-Free Vacation Rental Management

Full-Service
Management

We take care of everything: guest communication, marketing, professional cleaning, & property maintenance, ensuring your rental runs smoothly.

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More Bookings, Higher Profits

Our dynamic pricing strategies and expertly optimized listings help maximize your rental income while increasing occupancy rates.

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A Hands-Off
Experience

From booking inquiries to post-stay reviews, we manage every aspect of your rental, so you can enjoy the benefits without the hassle or stress.

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Get Your Property Listed On

  • Airbnb

    Airbnb

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    Pathway Properties

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    VRBO

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    Expedia

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    Hopper

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    Google

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Holly Drum, Founder of Pathway Properties
Hi, I'm Holly

More Than a Stay: The Heart Behind Pathway Properties

Hi, I’m Holly! I started Pathway Properties because I believe vacation rentals should be more than just a place to stay—they should feel like a home away from home. Whether you’re booking a scenic escape or looking for a stress-free way to manage your rental, I’m here to help make the process simple and enjoyable. My team and I take care of everything, from seamless guest experiences to hands-free property management, so you can focus on what matters most—making memories or maximizing your rental income without the hassle!

Travel Guides & Insider Tips

From scenic hikes to must-visit wineries, our local guides help you plan the perfect trip.

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