
Vacation rentals in Berryville
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Top-rated vacation rentals in Berryville
Guests agree: these stays are highly rated for location, cleanliness, and more.

COZY+SEXY Private Country Escape! HOT TUB & Views~
Look no further for privacy, intimacy, & fun~ Foxy is your perfect escape, located in the Shenandoah Valley & surrounded by a 1000 private acres but only 10 minutes from downtown Winchester. Offering a uniquely glamorous experience, surrounded by all the beauty of nature. Indulge in luxury & tranquility with amenities including your own private patio with hot tub and million dollar views of the Blue Ridge Mountains. Inside, a full chef's kitchen leading to a sexy, opulent master bedroom suite...

Pets? YES! Hot Tub | Fast Wi-Fi | Fire Pit
Moonflower Cottage is a historical farmhouse nestled on two rolling acres in Virginia's wine country. Visit the area's top vineyards, dining, and antique shops. Float down the Shenandoah River. Cap your day sipping cabernet as the sun sets and the cottage blooms like the moonflowers that grow wildly. Bathe in the warm glow of string lights under the grapevine arbor or enjoy a relaxing soak in the spa. Young or old, you are sure to find the vintage that you are looking for at Moonflower Cottage.

Guest Cottage on Historic Estate & Cattle Farm
Fully restored c.1900 farm house on 190 acre estate, ~1 hr from D.C. Cottage is situated at end of a farm road (past the main house and barns), very private w/ creek and cows right outside. Enjoy walks on the farm, local hikes, breweries & wineries, pick-your-own fruit farms, tubing on the Shenandoah, restaurants, antique shops, and more. 1 queen bdrm and bath on 1st flr, 2nd queen bdrm & loft with twin beds on 2nd flr. wifi, fire pit, small grill. Over 25 only, Max 4 adults. 1 SMALL DOG ONLY.

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.

Luxury Mountain Getaway: Sunsets, Wines & Views.
Celebrate your special moment in chic elegance and 5-star amenities for adult couples only. You deserve the Sunset Rouge. It's a destination in a relaxed and romantic setting to escape anxiety of kids, city, and work. Let the fun décor and panoramic views inspire the writer and artist within. During the day, take flight with eagles at eye level. At night, gaze into the heavens to catch a falling star. Within 2 miles is Lake Shannondale with beach access provided by the Mountain Lake Club.

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 Cottage at Stonecroft
Circa 1902, the Cottage is nestled at the foot of the Blueridge Mountains. The location will put you in touch with the history of the area, antique shops, wineries/breweries and nearby hiking. 2 bedrooms and bath upstairs; living room, dining table and full kitchen on main level (note ceilings in living/dining room are 6'3"). Wifi, fire pit and small charcoal grill. Absolutely no pets/animals. The property has video security system on the exterior of the property only.

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.

Blueridge Mountain Retreat Apartment
The hot tub is currently broken, and a new one has been ordered. We expect delivery by mid Febuary. In the middle of VA wine country and only minutes from the Appalachian Trail, enjoy a private apartment in our mountain home with a separate entrance and your own deck with views of the Shenandoah Valley. There is a hot tub on the deck and a fire pit overlooking the valley. Plenty of wildlife. A welcome basket includes breakfast items.

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.

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.
Popular amenities for Berryville vacation rentals
Other great vacation rentals in Berryville

Winchester Private Room

Charming Downtown Berryville!

Historic Loudoun Airwell Atelier

Cozy Bluemont Haven

Mountain lake retreat hot tub/pet friendly/winery

Modern House Barn on 66 acre Horse Farm

Upscale Walkup in Downtown Charles Town

The Serenity in DT Charles Town near Harpers Ferry
Frequently Asked Questions
Do guesthouse rentals in Berryville have air conditioning?
Absolutely! We offer over 10 guesthouse rentals with air conditioning in Berryville. Enjoy a tailored experience with all the comforts you desire.
Do guesthouse rentals in Berryville have a kitchen?
Absolutely! We offer over 10 guesthouse rentals with a kitchen in Berryville. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Berryville have wifi?
Absolutely! We offer over 10 house rentals with wifi in Berryville. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Berryville?
Experience the best of Berryville with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do guesthouse rentals in Berryville have free parking?
Absolutely! We offer over 10 guesthouse rentals with free parking in Berryville. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Berryville?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with air conditioning, over 10 homes with a kitchen, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
Quick stats about vacation rentals in Berryville

Total vacation rentals
Explore 20 vacation rentals in Berryville

Nightly prices starting at
Berryville vacation rentals start at € 25 per night before taxes and fees

Verified guest reviews
Over 530 verified reviews to help you choose

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
10 of Berryville vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Berryville rentals

4.8 Average rating
Berryville stays are highly rated by guests—averaging 4.8 out of 5!
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- Gambrill State Park
- Cacapon Resort State Park
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- Shenandoah River Outfitters
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- Big Cork Vineyards
- Harpers Ferry National Historical Park
- EagleBank Arena
- Cooter's Place
- Jiffy Lube Live
- Bluemont Vineyard
- Museum of the Shenandoah Valley
- Green Ridge State Forest
- Tysons Corner Center
- George Mason University




