Vacation rentals in Berryville

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!

Cameron Charmer pristine w/double master suites

Take a step into pure luxury in this newly renovated 1930's charmer in up and coming downtown area of Winchester. Owners have spared no expense to make this the kind of place where guests can come & forget about the rest of the world ! Incredible top of the line centralized dine in kitchen, wide open & inviting living areas, two master suites each with walk in closets & baths up lovely custom pine staircase. Come spoil yourself a bit at the Cameron Charmer, you are sure to enjoy your stay !

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!

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!

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.

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!

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.

Emma's Stone Cottage

Relax and unwind in the privacy of this wonderful stone cottage, which sits on 15 acres. In addition, it is located only 2.5 miles from I-81 and approx 10 miles from Winchester Medical Center, Old Town Winchester, Shenandoah University and much more. Our cottage has everything you need for a peaceful and enjoyable stay including full kitchen, central air, water softener, HD smart televisions, Wifi, outdoor firepit and more.

Snickers Gap Cottage

Historic cottage nestled in the foothills of the Blue Ridge Mountains, minutes from multiple breweries, wineries, hiking and biking trails, and the Shenandoah river. At just 40 miles west of Washington DC it’s the perfect weekend getaway to the country! We are known for our miles and miles of beautiful country roads. Come spend a weekend (or more!) and get lost in Loudoun.