Holiday houses in Middlebrook

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Top-rated holiday rentals in Middlebrook

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Top Guest favourite

Tent in Fairfield

4.98 out of 5 average rating, 1,158 reviews

Tipi with a great view of the Blue Ridge Mountains

Our small family farm is conveniently located 10 minutes from Interstates 81/64 and historic Lexington, Virginia. The Tipi has amazing views of the Blue Ridge Mountains and all the wonders our little farm and community has to offers. We are convenient to many local attractions like hiking, swimming, brewery and vineyard tours and yet secluded enough to heal your stress, enjoy time with your family or simply a special time away from the grind. Come stay with us! You deserve sincere hospitality!

Top Guest favourite

Tiny home in Staunton

4.94 out of 5 average rating, 143 reviews

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!

Top Guest favourite

Apartment in Staunton

4.97 out of 5 average rating, 148 reviews

Bee & Key—Staunton downtown

Staunton (pronounced “Stanton”) is one of the most vibrant, charming small towns you’ll find anywhere, and Bee & Key is in the center of it. This bright and stylish apartment is on the second floor of a grand 1885 home on East Beverley St. You will be half a block from the restaurants and shops of our bustling downtown, including Blackfriar’s Playhouse, the Woodrow Wilson Museum, The Shack restaurant, and Mary Baldwin University. We’re an easy walk from Staunton’s historic Amtrak station.

Guest favourite

Cabin in West Augusta

4.99 out of 5 average rating, 159 reviews

Between the Creeks

Welcome to "Between the Creeks", The 700sqft cabin is located between 2 Drafts (Creeks as we like to call them) You will drive over top Jonas Draft which flows into Ramsey's Draft located to the right about 500 ft. Ramsey's Draft is located behind the cabin which flows on the property! Enjoy the mountain views, listening to the frogs at the pond, and the water at the creek! Enjoy the piece and quiet! Just minutes from George Washington Natural Forest! Only about 30 minutes from Staunton.

Top Guest favourite

Farm stay in Raphine

4.98 out of 5 average rating, 375 reviews

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).

Top Guest favourite

Treehouse in Verona

4.99 out of 5 average rating, 179 reviews

The Laurel Hill Treehouse

Fully immerse yourself in nature in this serene Scandinavian-inspired woodland retreat, ideal for a couple's getaway. The treehouse is perfectly nestled amongst the trees, offering a chance to unwind while enjoying the beautiful views of nature. Just imagine yourself relaxing on the wrap around porch, soaking in the hot tub, cooling off in the creek, & cozying up to a crackling fire. We invite you to unwind, reconnect with nature & create cherished memories in this tranquil hideaway.

Top Guest favourite

Farm stay in Raphine

4.98 out of 5 average rating, 457 reviews

The Bread Barn

Welcome to Seasons' Yield Farm! Your retreat sits atop a working wood-fired bakery amidst a family farm in the beautiful Shenandoah Valley. Minutes off highway 81, within 20min 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 wood-fired bakery. Custom made coffees delivered to your doorstep every morning! Check us out at Seasons' Yield Farm. Welcome!

Top Guest favourite

Cabin in Vesuvius

4.98 out of 5 average rating, 242 reviews

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. We invite you to embrace our simpler way of life where we wholeheartedly believe that life is to be enjoyed and not endured.

Top Guest favourite

Cabin in Rockbridge Baths

4.97 out of 5 average rating, 351 reviews

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.

Top Guest favourite

Apartment in Staunton

4.95 out of 5 average rating, 366 reviews

Travelers Nook - close to downtown

The TRAVELERS NOOK is a cute, cozy, one bedroom apartment close to downtown Staunton! It’s located on the second floor, with a private entrance. It has all the charm that you would expect to find in a cute studio apartment! Built by a local architect Tj Collins in the 1920’s. This quaint space has everything you need to enjoy your stay here in Staunton! We do accept small pets on approval with a pet cleaning charge.

Top Guest favourite

Guesthouse in Staunton

4.93 out of 5 average rating, 648 reviews

The Firefly Springhouse

Private cabin, with bath, located in a quiet country setting, close to town and easy access to two Interstate highways. Comfy queen bed, 400 ct sheets. Climate control with state of the art Trane system. Mini-fridge, microwave, and Keurig coffee maker are included. High speed wireless internet and basic cable TV. All varieties of people are welcome here.

Guest favourite

Guesthouse in Waynesboro

4.92 out of 5 average rating, 402 reviews

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.

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Other great holiday rentals in Middlebrook

Top Guest favourite

Farm stay in Mount Sidney

5 out of 5 average rating, 6 reviews

Cabin 1 on 1Tribe Farm

ZackRating, 5 stars2 weeks ago

Absolutely perfect Air BnB! We had such a great stay. Cabins are a bit primitive with no heat or AC so be prepared - but we had everything we needed to have a comfortable night. The lounge areas and bathrooms/showers were the best part by far. The surrounding area is stunning as well. Can't wait to come back here for another trip to Shenandoah!

Guest favourite

Cabin in Montebello

4.94 out of 5 average rating, 32 reviews

Country Roads Take Me Home.

MichelleRating, 5 stars1 month ago

Cabin was even better than the pictures! Communication with host was fabulous as well as the peace and quiet the cabin provides! Would most definitely stay again!

Apartment in Staunton

5 out of 5 average rating, 5 reviews

The Staunton Nook (1BR/1B basement apt w/ kitchen)

KathyRating, 5 stars1 month ago

it was perfect for what me and my friends needed!

Top Guest favourite

Treehouse in Stanardsville

5 out of 5 average rating, 43 reviews

CloudPointe Retreat

KevinRating, 5 stars4 days ago

This place was awesome the views are incredible and the privacy was like nowhere else. As long as you have 4wd and don’t mind some steps this is a perfect place for couples. Everything was clean and exactly as described. Kevin was even proactive in letting us know the power had went out before we got there and then immediately let us know it was back on. This place really is a hidden gem and you are within 15-30 minutes of restaurants and shopping. We will definitely try to stay here again in the future.

Guest favourite

Home in Crozet

5 out of 5 average rating, 15 reviews

Orso Blu one-of-a-kind VIEWS in Crozet

JamesRating, 5 stars2 weeks ago

The house is in a beautiful setting surrounded by mountains with peaceful views from the front porch that include a field of lavender and a stream. A forested trail network can be accessed at the far end of the lavender field--so bring your hiking shoes. The house is stunning with clean lines, "european" design and decor that includes high-end appliances and fixtures. Francesca is the ultimate host-very friendly and helpful. She provided all the information and details on the house that you would need for an easy check-in, stay, and check-out. From my initial conversations with her when I booked the house to helpful messages just before and during our stay, I felt like I was staying at the house of an old friend. We look forward to staying at Orso Blu on a future trip!

Top Guest favourite

Cabin in Millboro

5 out of 5 average rating, 93 reviews

Cloverdale Cabin Nature Secluded Retreat

KellyRating, 5 stars3 months ago

We had an amazing stay at this cabin! The space was cozy, clean, and beautifully decorated, with all the amenities we needed for a relaxing getaway. The location was perfect, offering both privacy and breathtaking views. The hosts were incredibly friendly and attentive, making sure we had everything we needed. We truly felt at home and can't wait to return. Highly recommend for anyone looking for a peaceful retreat

Top Guest favourite

Cabin in Montebello

5 out of 5 average rating, 26 reviews

Tyebello Cabin 5

KatieRating, 5 stars5 months ago

Spent New Year's with my husband and two Yorkies nestled deep in the woods, and it was everything I hoped for—and more! The property is surrounded by towering trees, offering a sense of tranquility and seclusion that's hard to come by. The bed deserves a special mention— it was the most comfortable bed I’ve ever slept in! We spent all three days hiking some of the best trails and relaxed comfortably watching TV in the evenings with a nice glass of Malbec. If you're looking for a peaceful retreat where you can reconnect with nature without sacrificing comfort, this Airbnb is the perfect choice. I’ll definitely be returning! Thank you Jerry and Chris.

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