Holiday houses in Middlebrook

Staunton Escape 👑King Bd, washer+dryer+Wifi+Fence

This 2 story house with vaulted ceilings is situated close to downtown Staunton in the heart of the Shenandoah Valley. Access to Shenandoah Nation Park and the Blue Ridge Parkway is just a short drive. This unique space has a King and Queen bed on the 1st floor, and a twin bed, futon, sofa bed and section on the 2nd floor. The ample parking allows for multiple large vehicles. The yard has a covered seating area and is completely fenced in. Wifi is fast, 58in smart TV, hand crafted decor, privacy

Location · Family · Amenities

Bee & Key—Staunton downtown

This bright and stylish apartment is on the second floor of a grand 1885 home on East Beverley St. in downtown Staunton. 2BR/1BA can sleep up to 6 if you don’t mind being cozy! • king bed in main bedroom (2) • day bed with trundle in small adjoining bedroom (2) • sofa bed in living room (1) • good air mattress (1) Bee & Key is a few steps from the restaurants and shops of our vibrant downtown, plus Blackfriar’s Playhouse, Woodrow Wilson Museum, Mary Baldwin University and the Amtrak station.

Family · Value · Barbecue

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.

Family · Location · Check-in

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!

Location · Value · Decor

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).

Family · Location · Condition

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.

Family · Location · Checkout

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!

Value · Family · Air conditioning

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!

Family · Location · Access

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.

Family · Value · River

* Award-Winning Renovation * Ideal Location *

— Off-Street Parking — Cleaning & Linens taken care of for you — Prepare a meal in the fully equipped kitchen. Relax on the porch as the sun sets behind the nearby mountains. Or sink into your own king-size bed with a good book. This downtown home was painstakingly renovated to highlight its historic character and is a proud recipient of the Historic Staunton Foundation's 2021 Residential Rehabilitation Award. Welcome to NEWTOWN RETREAT!

Location · Family · Layout

Maury River Cabin w/ Private Access near WLU & VMI

Welcome to Home Place on the Maury, a historic 1700s log cabin in Virginia’s Shenandoah Valley with direct Maury River access. This charming getaway blends rustic history with modern comfort, featuring screened porches, two fireplaces, and 15+ acres of grounds. Perfect for families, history lovers, and outdoor enthusiasts. Kayaks and river floats are provided for relaxing or adventurous days on the water.

Location · Family · Hiking

The Storefront: Downtown Staunton + Unique Stay

Welcome to The Storefront: A Very Small Hotel. The Storefront is located right in the heart of downtown Staunton. The Storefront was built in the early 1900's and was previously a tea shop before becoming a vacation destination. It's like having your own little townhouse in the heart of Staunton's historic district! Keep your car parked and walk everywhere you need to go.

Location · Value · Bathroom