Holiday rentals in Berryville

4.87 out of 5 average rating, 230 reviews

Home in Bluemont

The Old Schoolhouse at High Meadows Estate

The Old Schoolhouse at High Meadows is a beautifully appointed historic cottage set amidst a tranquil 50 acre estate of gardens and old barns. Close to wineries, breweries, the Appalachian and W&OD Trails and many historic villages (Middleburg, Upperville, Harpers Ferry) and only minutes from the Shenandoah River, this superbly decorated cottage is a wonderful get away from Washington DC and perfect for a couple or small family. Activities abound, or just visit local farmers’ markets and read.

4.99 out of 5 average rating, 542 reviews

Cabin in Bluemont

Rustic Blue Ridge Cabin

A quaint rustic cabin nested at the top of the Blue Ridge Mountains, with a detached 150 ft² bedroom, located in the heart of Western Loudoun Wine Country. Sitting on 1/3rd of an Acre with access to wooded a trail featuring Cold Springs. Amenities- 4person hot tub, beautiful view of the Loudoun Valley, Wifi, Loft bedroom with a loft ladder, hiking along the Appalachian Trail,Shenandoah River, with restaurants, breweries, distilleries, and wineries close by!This is a rustic not luxurious cabin!

4.99 out of 5 average rating, 110 reviews

Farm stay in Bluemont

Welcome to the Hidden Hive!

The Hidden Hive is located on beautiful, tranquil farmland, within a few minutes of Loudoun County’s premiere wineries and breweries. Rest your head here after a hard day’s hike on the Appalachian Trail or a celebratory evening at a Bluemont wedding. We are a hobby farm and own chickens, goats, dogs, and barn kitties. Wildlife such as deer can be seen, and owls heard here at night. You may see cyclists or horseback riders pass along our historic Civil War roads. We can’t wait to host you!

5 out of 5 average rating, 209 reviews

Flat in Winchester

Old Town Loft In Highly Desirable Area Downtown

Location, Location! A completely renovated apartment in the highly desirable center Winchester. You’ll still be able to see some of its original character throughout this historic building. The apartment has a fully stocked custom kitchen with reclaimed wood and quartz counters, coffee nook with Keurig, large tile shower with glass doors, hardwood floors, queen memory foam mattress, high speed Wi-Fi, 50’ smart TV, Xfinity HDTV with voice remote control, AC/Heat, Washer/Dryer, and dishwasher.

Superhost

Loft in Winchester

4.72 out of 5 average rating, 658 reviews

Immerse yourself in Old Town Winchester (Apt #4)

Our loft apartment is in the heart of Old Town Winchester on the Old Town Mall. Located off of a little alley, with security lighting and motion detectors you will be staying steps away from dining, shops, and everything our community has to offer. Yet, our apartments are quiet and secure. Our building is OLD & has all of the charm that goes along with it. If you are looking for a sparkly new place, you may want to stay elsewhere, If you want clean, funky, and awesome, we are your place!

4.97 out of 5 average rating, 254 reviews

City Charmer minutes from Old Town

Renovated 1950's cottage style home. Enjoy a small house with a great front porch and large backyard with patio. Just minutes to drive and about 10-15 minutes to walk to Historic Old Town Winchester which includes numerous restaurants, bars, shopping, and often some kind of event like the Shenandoah Apple Blossom Festival! Our house is located about 65 miles West of Washington D.C. if you're looking for a day trip to the big city or just sit back and relax right here in our small town.

Farm stay in Round Hill Village

4.93 out of 5 average rating, 412 reviews

The Goat Loft - A Private, Peaceful Getaway!

Private Blue Ridge Retreat – Nature, Hiking, and Relaxation Escape to 13 acres of peaceful woodlands and pasture at the base of the Blue Ridge Mountains. Enjoy the goats from the private deck, perfect for stargazing at night! Nearby, hiking on the Appalachian Trail, cycle scenic routes, or explore historic towns, wineries, and breweries. The Potomac and Shenandoah Rivers offer even more outdoor adventures. A perfect mix of tranquility and adventure, but just minutes from everything!

4.94 out of 5 average rating, 214 reviews

Cabin in Front Royal

The Wizard's Chalet • Cozy nature escape • Hot Tub

Looking for a fun getaway in a relaxing, secluded spot? Come visit The Wizard's Chalet, a cozy & upgraded cabin located in the Shenandoah Valley just one mile from Shenandoah River access and a few miles from restaurants, wineries, basketball & volleyball courts, and more! With a fully stocked kitchen, three cozy bedrooms, high speed WIFI, hot tub, and several beautiful outdoor gathering spaces, this magical cabin is perfect for couples, friends, or the entire family!

4.87 out of 5 average rating, 163 reviews

Farm stay in Bluemont

24 Acre Lamontagne Farm House

Located at the base of the Blue Ridge Mountains in Bluemont, VA only 20 minutes from Leesburg, 5 minutes from Bluemont Vineyards, Dirt Farm Brewing, 10 minutes to B Chord Brewing and Bear Chase, and Henway Cider. This perfect historic house has so much charm and character to offer it makes the perfect getaway for visiting Loudoun County. The other bedrooms are left vacant on purpose and not for occupancy. Please reach out for recommendations : )

4.93 out of 5 average rating, 245 reviews

Townhouse in Winchester

Modern Elegance in Historic Old Town Winchester

Just a block and a half from the Old Town Winchester pedestrian mall, this historic beauty with modern elegance is sure to please. You are within walking distance of quaint shops, great restaurants, The Brightbox Theater, and The Shenendoah Discovery Museum. Spend the day touring the areas great wineries or enjoying Skyline Drive, and then return to enjoy a great night out, or an evening at home making dinner in the spacious modern kitchen.

4.97 out of 5 average rating, 233 reviews

Full basement with private entrance. Hot tub

Cozy movie themed basement is exactly what you are looking for. Classic AirBnB-we are opening our house to you! Space is completely private. Bedroom with queen bed. High speed internet. Private bath w/shower. Small refrigerator, microwave, 2 flat screen TVs table and chairs and multiple couches in a large family room w/Sofa bed. 1000 square feet of space! Home 2 miles outside of the city of Winchester in Frederick County.

Guest house in Round Hill Village

4.97 out of 5 average rating, 454 reviews

Private Carriage House

A recently renovated carriage house by an interior designer situated on a treed and private property conveniently located for exploring wineries, breweries, horse events or civil war sites in Middleburg, Purcellville, Leesburg, Bluemont or Round HIill. Enjoy the sounds and sights of nature and fresh air. Recharge in a peaceful setting. Adults only. No pets, children or infants.

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Other great holiday rentals in Berryville

Guest house in Stephens City

5 out of 5 average rating, 17 reviews

Ventura Cottage: 360-views/HotTub/4 acres/Gym

JosetteRating, 5 stars2 months ago

Everything was top notch, pictures don't do the location justice. The ambiance is peaceful quiet fresh air beautiful views, the house is as listed and more, You get what you paid for. Leena is an amazing person very responsive and very hospitable. Don't think twice just book you will not be disappointed.

5 out of 5 average rating, 6 reviews

Home in Berryville

Purple Iris 3b 2b private oasis nr river/mountain

MeaganRating, 5 stars8 months ago

My sister was visiting from Canada so we decided to head to Virginia to hit some wineries and breweries. We had a lovely stay at Elizabeth’s place! It looked just like the photos, was clean and cozy, and a perfect place to unwind at the end of the night with a glass of wine. The hosts texted us recommendations of stuff to do in the area and we had an amazing time. Great couch and TV set up, very comfortable beds, and beautiful wooded surroundings. Highly recommend for any trip to the area!

Barn in Berryville

4.78 out of 5 average rating, 120 reviews

Modern House Barn on 66 acre Horse Farm

LisaRating, 5 stars2 months ago

This place is tucked into a little peace of heaven. Very peaceful and easy to get to. The interior is nicely designed, furnishings are comfortable. The kitchen has a little eat in area with plenty of space to sit and chat, eat, play board games, or cook. I loved that the bedrooms were upstairs so if someone wanted to sleep, it’s quiet enough to do that. The upstairs is quite sound proof. There’s also a nice little tv area upstairs between the two rooms. The rooms have plenty of space to store clothes if you are staying longer. The outside area also has a picnic table and grill which would be nice when staying in the warmer months. The hosts were very kind and responsive. They answered any questions we had quickly. I highly recommend this place and hope to stay again when we come back.

4.86 out of 5 average rating, 37 reviews

Flat in Winchester

Dreamweaver Bright 1BR 2 blocks to Walking Mall

EricRating, 5 stars5 months ago

Great place with a lot of character and nice touches. Wonderful location. Would definetly stay again!

4.94 out of 5 average rating, 85 reviews

Farm stay in Bluemont

Private apt with views on a beautiful horse farm

ElisabethRating, 5 stars1 week ago

I am a repeat guest and absolutely will be again in the future. Love the space, and the gorgeous farm and location. Hosts are so friendly and helpful. The farm flowers are always such a nice touch and the covered porch is convenient. Bed is comfortable and the internet is great! Everything you need :)

4.99 out of 5 average rating, 81 reviews

Apartment in Winchester

Historic District Downtown Winchester

PattyRating, 5 stars1 week ago

Great spot and beautifully decorated. Close to lots of eating places.

4.95 out of 5 average rating, 60 reviews

Misty Meadow has quite setting in the country.

FaithRating, 5 starstoday

This was our second visit to Marie's beautiful home and definitely not our last! Her house is very clean and comfortable. We loved sitting in the yard watching the wildlife and listening to all the different bird songs. We had a very relaxing visit and Winchester has some yummy restaurants. We loved our visit!