Holiday rentals in Middlebrook

Ultimate cabin in the mountains

This unique and secluded cabin sits on 75 acres in the Blue Ridge mountains. Enjoy the cozy wood fireplace, hot tub, charcoal grill, and fast, reliable fiberoptic internet if you need to get some work done while you're away. It has a washer and dryer, a full kitchen, and is pet-friendly (no pet fee!), so you can enjoy it with the whole family. There is a 4K 55” smart TV with apps, a Tesla LVL 2 charger, a cabinet full of board games, books, and plenty of items to entertain both kids and adults!

Mountain Overlook House - Blue Ridge Parkway

Unique octagonal house with stunning views of the Blue Ridge Mountains of Virginia. Located 2 miles from I-64, 15 minutes to downtown Waynesboro and an easy 25 min drive to Charlottesville and UVA. Open floor plan, perfect for gathering, and long-range 180 degree views from nearly every room. Fully equipped renovated kitchen. Quality linens and bedding. Rustic, yet modern decor. Home features large fireplace, outside fire pit, wifi, and board games galore. Stargazing and birdwatching heaven.

Sunrise Casita: a tiny house at Cana Barn

Our 250 sq ft tiny house was built by our talented craftswoman Kara. We used wood from our property and reclaimed materials to create a cozy and unique getaway. The front porch looks out to a beautiful view of the Blue Ridge Mountains and looks up to a local vintage sign. We are LGBTQ+ welcoming. Sunrise to us is the embodiment of a fresh start and a new opportunity. It is hope and possibility, adventure and inspiration, beauty and wonder. We hope all of this for your stay in our tiny house!

Solitude- A Tranquil Riverfront Experience

Come and enjoy the peace and beauty that Solitude has to offer. This newly renovated cottage sits on the beautiful Maury River offering relaxation for those looking for a getaway, while also boasting one of the most desirable spots on the Maury for a fun swim, fishing, or a nice float from Beans Bottom to Jordan's Point! Located just 5 minutes from Lexington, you can be in the heart of downtown in just minutes and enjoy all of the attractions that Lexington/Rockbridge County has to offer.

Creekside Retreat | Fire Pit + Big Fenced Yard

Wake up to the sound of the creek and end your evenings around the fire-pit in your fully private, fenced yard. Bear Creek is a peaceful, private Blue Ridge retreat designed for couples, families, and pet-friendly getaways. Inside enjoy three comfortable bedrooms, an open living space, and direct access to a gently babbling creek just steps from the backyard. Minutes to Crabtree Falls, the Appalachian Trail, and Nelson County wineries--yet tucked away in a quiet, relaxing setting.

The Sanctuary

Nature lovers paradise! Named "The Sanctuary" for the place you can UNPLUG, unwind & find your peace! Perched up high on nearly 60 acres- you are sure to get fresh air & the rest you are searching for! Only 4 miles to Wintergreen, 6 miles to Sherando lake and backs up to the Blue Ridge Parkway there are plenty of things to do OR just relax and enjoy the crickets & stars! With crazy careers, growing kids & constant hustle- everyone needs a hide out like this every now and then!

The Laurel Hill Treehouse

Tucked away in the woods, this Scandinavian-inspired treehouse is a quiet, peaceful spot designed for a relaxed couples getaway. Surrounded by trees and overlooking beautiful woodland views, it’s an easy place to slow down and unwind. Spend your time on the wraparound porch, soak in the hot tub, cool off in the creek, or settle in by the fire at night. This is a serene, comfortable retreat where you can reset, enjoy all that nature has to offer, and simply be present.

Spring Mountain Views + Hot Tub near WLU & VMI

Amazing contemporary home features a stunning mountain view from the hot tub patio and a spacious open layout filled with vintage furniture. This piece of paradise located on 6 private acres is the perfect weekend mountain escape! 15 minutes to downtown Lexington, W&L, VMI. 10 minutes to the Virginia Horse Center. Minutes from Ecco Adesso Vineyard and Rockbridge Winery. Sunrise Ridge is a pet-friendly property, we warmly welcome your pets with a pet fee of $150.

CloudPointe Retreat

Rare Appalachian Treehouse Gem! Luxurious, one-of-a-kind retreat for couples. Elevated tiny house among the treetops, private parking, plush bedroom, sleek bathroom, beautiful kitchenette, loveseat, lounge, private double-level decks, fireside lounging (wood provided), gas grill, and patio with a hot tub! Surrounded by nature, with wineries, hikes, restaurants and shopping all nearby. Please come and relax and revel in the beauty of nature! 4WD is recommended.

Little Cabin in the Woods is quiet and secluded!

Enjoy our rustic, cozy, historic log cabin in the woods on 21 acres with two streams and a little meadow. The logs, from the 1800's, were reconfigured 17 years ago combining a rich history with high speed internet and modern amenities. Sink into the luscious bed with totally organic sheets, mattress topper, and pillows. Take a walk on the original wagon train road down to a stream or bath your senses in the majestic view of Jump Mountain from the meadow.

The Bread Barn

Welcome to Seasons' Yield Farm! Your retreat sits atop a working bakery amidst a family farm in the beautiful Shenandoah Valley. Minutes off highway 81, within 20 minutes of Lexington and Staunton. This getaway is perfect for the guest passing through or a family looking for a rural getaway. Enjoy the solitude of the country and the yield of a bakery! Custom made coffees delivered to your doorstep every morning! Check us out at Seasons' Yield Farm. Welcome!

The Stable

Our guesthouse is located in the historic Tree Streets Neighborhood of Waynesboro, VA, an official Appalachian Trail town, located at the southern end of the Shenandoah National Park. We've aptly named the guesthouse "The Stable" because it was originally built and functioned as a stable. It has since been converted into a cozy cottage for guests.