Vacation rentals in Berryville

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Top-rated vacation rentals in Berryville

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Guest favorite

Guest suite in Summit Point

4.97 out of 5 average rating, 128 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!

Jan 12 – 19

$111 per night

Guest favorite

Cottage in Berryville

4.98 out of 5 average rating, 115 reviews

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.

Apr 22 – 29

$225 per night

Guest favorite

Cottage in Bluemont

4.95 out of 5 average rating, 169 reviews

The Cottage at Stonecroft

Nestled at the foot of the Blue Ridge Mountains among beautiful rolling hills, on a working horse farm outside the village of Bluemont. This circa 1902 Cottage will put you in touch with the history of the area, antique shops, wineries/breweries and nearby hiking. 2 bedrooms and bath upstairs; sitting/living room , dining table and full kitchen on main level. Wifi, fire pit and small charcoal grill. Over 21 only. Absolutely no pets/animals. For your safety property has video security system.

Nov 19 – 26

$124 per night

Guest favorite

Farm stay in Round Hill

4.94 out of 5 average rating, 346 reviews

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.

Sep 30 – Oct 7

$108 per night

Guest favorite

Apartment in Winchester

5.0 out of 5 average rating, 137 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.

Sep 29 – Oct 6

$144 per night

Guest favorite

Apartment in Winchester

4.94 out of 5 average rating, 270 reviews

Downtown 1920's Gas Station

Luxury 1920’s Refurbished Gas Station repurposed into a beautiful apartment. Private off-street parking/EV car charging station, full kitchen, custom shower with rain system, super high speed wifi, smart TV & Blu-Ray. Plenty of light with frosted garaged doors. AC/Heat, Washer/Dryer, Dish Washer, coffee nook, and open living design. Be a part of Old Town Winchester in this unique fun space in walking distance to breweries, neighborhood Pizzoco Pizza parlor and the downtown walking mall.

Jul 16 – 23

$122 per night

Guest favorite

Home in Winchester

4.98 out of 5 average rating, 151 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!

Dec 15 – 22

$133 per night

Guest favorite

Home in Bluemont

4.93 out of 5 average rating, 202 reviews

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.

Feb 22 – Mar 1

$124 per night

Guest favorite

Cottage in Winchester

4.97 out of 5 average rating, 421 reviews

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.

Aug 22 – 29

$106 per night

Guest favorite

Townhouse in Winchester

4.95 out of 5 average rating, 169 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.

Aug 4 – 11

$85 per night

Guest favorite

Loft in Purcellville

4.99 out of 5 average rating, 286 reviews

"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.

Oct 2 – 9

$99 per night

Guest favorite

Home in Berryville

4.95 out of 5 average rating, 189 reviews

Riverfront Getaway w/ Breathtaking Views!

Welcome to the Shenandoah Valley! Expect a private, serene, and relaxing experience! Our newly renovated home has great deck space and beautiful views right on the Shenandoah River! Enjoy river tubing, fishing, kayaking, reading a book by the fire, or drinking coffee on the porch while watching a breathtaking sunrise! Conveniently located an hour west of DC and 25 minutes east of Winchester.

Sep 6 – 13

$267 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Berryville vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Berryville's top sights

The Berryville Grille15 locals recommend

Santorini Grill11 locals recommend

Camino Real Mexican Restaurant11 locals recommend

Nalls Farm Market8 locals recommend

Cordial Coffee Co.17 locals recommend

Martin's Food3 locals recommend

Other great vacation rentals in Berryville

Guest favorite

Apartment in Charles Town

4.96 out of 5 average rating, 481 reviews

Private efficiency apartment

Jul 25 – Aug 1

$72 per night

Guest favorite

Home in Winchester

4.97 out of 5 average rating, 165 reviews

Cameron Charmer pristine w/double master suites

Aug 2 – 9

$111 per night

Guest favorite

Home in Inwood

4.96 out of 5 average rating, 375 reviews

The Inwood House- easy on/off I-81

Oct 7 – 14

$96 per night

Guest favorite

Cabin in Bluemont

4.98 out of 5 average rating, 446 reviews

Rustic Blue Ridge Cabin

Nov 11 – 18

$147 per night

Guest favorite

Cottage in Martinsburg

4.98 out of 5 average rating, 353 reviews

Last Rodeo Cottage

Nov 19 – 26

$98 per night

Superhost

Barn in Berryville

4.81 out of 5 average rating, 83 reviews

Modern House Barn on 66 acre Horse Farm

Jul 14 – 21

$95 per night

Guest favorite

Home in Berryville

5.0 out of 5 average rating, 18 reviews

Vidalia House in Berryville, The Whole Onion

Jul 31 – Aug 7

$166 per night

Guest favorite

Cabin in Berryville

4.97 out of 5 average rating, 37 reviews

Deer Chase

Mar 30 – Apr 6

$225 per night

Show all

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 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 free parking, over 10 homes with air conditioning, over 10 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.

Vacation rentals in Berryville

Top-rated vacation rentals in Berryville

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Berryville vacation rentals

Stay near Berryville's top sights

Other great vacation rentals in Berryville

Apartment in Charles Town

Home in Winchester

Home in Inwood

Cabin in Bluemont

Cottage in Martinsburg

Barn in Berryville

Home in Berryville

Cabin in Berryville

Quick stats about vacation rentals in Berryville

Total rentals

Popular amenities

Wifi availability

Rentals with dedicated workspaces

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Do guesthouse rentals in Berryville have air conditioning?

Do house rentals in Berryville have a kitchen?

Do house rentals in Berryville have wifi?

How much does it cost to stay in house rentals in Berryville?

Do guesthouse rentals in Berryville have free parking?

What are the most popular amenities for Guesthouse Rentals in Berryville?

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