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Vacation rentals in Berryville

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Top-rated vacation rentals in Berryville

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Cottage in Berryville

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.

Home in Winchester

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 !

Farm stay in Round Hill

Come and get your goat on!

Nestled at the base of the Blue Ridge and tucked away in the woods, we offer a quiet and peaceful get away while being convenient to tons. Enjoy the peace of 13-acres of woodlands and pasture. A large private deck provides a plenty sun with pasture and woodlands views with some great star watching at night. Miles of walking, the Appalachian trail, fantastic cycling; historic towns and places; wineries, breweries, and distilleries; Potomac and Shenandoah rivers. All just minutes away.

Rental unit 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.

Cottage in Winchester

Lockley Cottage at Historic Perry Farm

Peace and tranquility await you at a quaint cottage on historic Perry Farm, where the original 19th century farmhouse still stands today. Stroll several acres of land and enjoy pastoral views while you unwind at this peaceful historic property in the hills of northern Shenandoah Valley. This rural retreat is easily accessed from I-81 and located a short 10-minute drive from historic downtown Winchester. Enjoy local wineries, breweries, farm markets, and the renowned Apple Blossom Festival.

Home in Bluemont

The Country French Cottage at High Meadows Estate

Come visit the alluring wine country of Bluemont Virginia, and stay in a beautifully appointed country French cottage on the 50 acre circa 1896 High Meadows Estate atop the Blueridge Mountains. Just 50 minutes west of Washington DC, this stunning country retreat is just 5 minute from the vineyards of Bluemont, the Shenandoah River, the Appalachian Trail, Hiking, Canoeing, Kayaking, Farmers Markets, the the cute villages or Berryville, Harpers Ferry, Luckettes, Middleburg and many more.

Home in Winchester

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.

Cottage in Winchester

Emma's Stone Cottage

Relax and unwind in the privacy of this wonderful stone cottage, which sits on 15 beautiful acres. In addition, it is located only 2.5 miles from I-81 and 14 minutes from Winchester Medical Center, Old Town Winchester, Shenandoah University and much more. Our cottage is fully furnished with all the comforts of home. From the full kitchen, central air, water softener, HD smart televisions, Wifi, outdoor firepit and more. It has everything you need for a peaceful and enjoyable stay.

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.

Loft in Purcellville

"When Pigs Fly" Airbnb Most Hospitable Host in VA

Located between Middleburg, VA and Purcellville, VA, our loft is just about 15 minutes away from restaurants, wineries, breweries and many local points of interest. You will have views from every window in addition to all of the amenities you will need for a pleasant stay. We welcome your dogs while you visit. The only thing we ask is that you keep them off the couch, pick up their "business" and crate them if they are left alone.

Guesthouse in Round Hill

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.

Cottage in Bluemont

Wine Country Cottage

Cottage in the heart of wine country! Access 4 wineries within a 5-mile radius as well as the AppalacionTrail, breweries, hikes, and historic battlefields. 1 min drive/5 minute walk to Shenandoah River. Check-in and check-out can be somewhat flexible with advance notice. If you need a different time feel free to ask. Pet friendly with a non-refundable fee.

Vacation rentals for every style

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Homes

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Popular amenities for Berryville vacation rentals

Free parking on premises

Air conditioning

Other great vacation rentals in Berryville

Cottage in Martinsburg

Last Rodeo Cottage

Guesthouse in Bluemont

Blueridge Mountain Guest Cabin- Amongst the Trees

Rental unit in Winchester

Downtowner

Cottage in Winchester

Uber SXY Private Country Escape! Hot Tub & Views~

Rental unit in Winchester

Downtown 1920's Gas Station

Rental unit in Bluemont

Charming private apartment

Cottage in Bluemont

The Cottage at Stonecroft

Cabin in Bluemont

Rustic Blue Ridge Cabin

Quick stats about vacation rentals in Berryville

Total rentals
20 properties
Popular amenities
Kitchen, Wifi, and Pool
Wifi availability
10 properties include access to wifi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Total number of reviews
370 reviews
Nightly prices starting at
$30 before taxes and fees

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 house rentals in Berryville have a kitchen?
Absolutely! We offer over 10 house 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 guesthouse rentals in Berryville?
Experience the best of Berryville with our guesthouse rentals, starting at about $170 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Berryville have free parking?
Absolutely! We offer over 10 house rentals with free parking in Berryville. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Guesthouse Rentals in Berryville?
Enhance your stay in our Guesthouse Rentals with the most popular amenities: 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.

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