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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.

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Home in Bluemont

4.87 out of 5 average rating, 220 reviews

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.

Guest suite in Summit Point

4.97 out of 5 average rating, 151 reviews

The Big Room - Historic Schoolhouse

Located one mile from the racetrack in the little village of Summit Point. This is a large renovated former classroom with 13' ceilings in the old Elementary School. Summit Point is a quiet place where you can take a leisurely stroll. There are even a couple sidewalks ;) We have 3 churches and a post office. The "Railside Market" serves food and sundries one block away. (currently has limited hours) Multiple food options are available in nearby Charles Town and lots more in Winchester Virginia!

Cabin in High View

4.97 out of 5 average rating, 104 reviews

Mary's Cabin

Nestled on 2 acres in the woods of West Virginia, kick back and relax in this quiet, chic cabin. Soak in the oversized copper tub, read on the porch swing, or cuddle by the electric fireplace. All the amenities of home, but away from the hustle and bustle of daily life. Only 25 minutes to quaint Old Town Winchester, where there are unique shops, breweries, restaurants and history! The cabin is located 20 minutes from a variety of scenic hiking trails that provide opportunities for adventure.

Rental unit in Winchester

5 out of 5 average rating, 175 reviews

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

4.91 out of 5 average rating, 132 reviews

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 Winchester

4.97 out of 5 average rating, 173 reviews

Colonial Getaway Near Old Town Historic Winchester

Colonial style home- enjoy a spacious home with large living room, dining room, kitchen, 3 bedrooms and 2.5 bathrooms. Perfect for a family or a longer stay. Just a few miles drive to Old Town Winchester which includes numerous restaurants, bars, shopping and some kind of event... like the Shenandoah Apple Blossom Festival! Our house is located about 65 miles West of Washington D.C. Near by to other scenic attractions as well- Shenandoah National Park, Luray Caverns, and Harper's Ferry!

Barn in Berryville

4.79 out of 5 average rating, 107 reviews

Modern House Barn on 66 acre Horse Farm

Enjoy your stay at this completely renovated and unique barn home on a 66-acre horse farm with sweeping meadow and mountain views nestled between wine country and the Blue Ridge Mountains. This stay will allow you the peace and tranquility of farm life, while only being 5-10 minutes from restaurants, grocery stores, hiking trails, overlooks, coffee shops, breweries, and some of wine countries best wineries! Horse boarding & stall available upon request for an additional charge!

Cottage in Bluemont

4.95 out of 5 average rating, 192 reviews

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.

Townhouse in Winchester

4.93 out of 5 average rating, 213 reviews

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.

Cottage in Winchester

4.97 out of 5 average rating, 469 reviews

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.

Cottage in Bluemont

5 out of 5 average rating, 108 reviews

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.

Cottage in Bluemont

4.81 out of 5 average rating, 224 reviews

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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Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Berryville vacation rentals

Free parking on premises

Air conditioning

Stay near Berryville's top sights

Cordial Coffee Co.17 locals recommend

The Berryville Grille15 locals recommend

Barns of Rose Hill12 locals recommend

Santorini Grill11 locals recommend

Camino Real Mexican Restaurant11 locals recommend

Hip and Humble9 locals recommend

Other great vacation rentals in Berryville

Home in Bluemont

5 out of 5 average rating, 4 reviews

Cozy Bluemont Haven

Farm stay in Bluemont

4.99 out of 5 average rating, 98 reviews

Welcome to the Hidden Hive!

Rental unit in Winchester

4.98 out of 5 average rating, 101 reviews

Cozy Apartment located on our 5-acre property

Rental unit in Winchester

4.95 out of 5 average rating, 39 reviews

Easy like a Sunday Morning 1 BR apt great location

Cabin in Gerrardstown

4.89 out of 5 average rating, 211 reviews

Modern Eclectic Cabin with Views - Hot Tub - Creek

Rental unit in Winchester

4.93 out of 5 average rating, 85 reviews

Newly repurposed Historic Home in Winchester VA!

Cottage in Berryville

4.98 out of 5 average rating, 97 reviews

Milton Valley Cottage on Historic Estate Farm

Home in Summit Point

5 out of 5 average rating, 15 reviews

Summit Point Historic "1850's House"

Quick stats about vacation rentals in Berryville

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

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 Guesthouse Rentals in Berryville?
Enhance your stay in our Guesthouse Rentals with the most popular amenities: over 10 homes with a kitchen, over 10 homes with free parking, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

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