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!

Serenity by the Stream

Cabin in the Shenandoah Mountain surrounded by National Forest on 3 sides. Inside cozy atmosphere with warm lighting and local landscape art throughout. Bright and cheery in the bedrooms best suited for 2-4 adults or family with children. Wonderful sound of the river throughout the property. Step outside to hundreds of miles of biking and hiking trails, and stocked lakes and streams. Well maintained paved state road to cabin driveway. The house is 20 minutes West of Harrisonburg VA and JMU.

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!

The Cottage at Hidden Valley Farm & Barn

Welcome to Hidden Valley! When booking your stay, you'll have exclusive access to our three bedroom/two bathroom guest cottage! You'll be surrounded by mountainous views and pastures. Snuggle on the wrap around porch, roast marshmallows in the fire pit, and visit with horses, cattle, and our Sulcata tortoise! This is a working farm and you'll frequently see and hear farm machinery(tractors/atvs/etc.), livestock (cattle/horses/a donkey/4 dogs/a cat),and wildlife (coyotes/turkeys/deer).

The Firefly Cottage

This century old cottage, updated with modern comforts, is perfect for a long or short stay and is located on our family farm. Minutes from downtown Staunton or Interstates 81/64. Relax, stretch out in four rooms, get some laundry done. Enjoy the peace of the rural setting. Queen size bed, large shower, fully equipped kitchen with dishes, cooking utensils, range/stove, microwave, refrigerator, and dishwasher. Washer and dryer. Private parking. All varieties of people are welcome here.

Luxury Cottage | Outdoor Tub + Mountain Views

Soak in a private outdoor bathtub beneath the stars, wake to mountain views from your king bed, and open an entire wall of glass to bring the Blue Ridge Mountains inside. Welcome to The Cottage at Perkins Hollow Retreat! Located in Nelson County, just minutes from the Nelson 151 Brew Trail, award-winning wineries, breweries, hiking, and only 25 minutes from Charlottesville, The Cottage is the perfect destination for a romantic getaway, anniversary, honeymoon, or peaceful retreat.

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!

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!

Whimsical Creekside Cabin

Escape to our cabin in the Blue Ridge Mountains! Fall asleep to sounds of Little Mary’s Creek, enjoy your coffee on the wrap around deck, or delight in exploring your own 7 acres in the forest. Our cabin is a cheerful, clean, and private cottage to come home to- or spend your days on property splashing in the creek and sitting out by the fire pit.

Blackwood Air B & B

Enjoy this spacious dwelling while viewing the Blue Ridge Mountains, Watch the freight train make its way around the curve or listen to the sheep as they graze in the pasture. Nearby outdoor activities are various hiking trails, Skyline Drive Parkway, or a local Shenandoah Acres lake. Only 10 miles from Wintergreen Resort.