Do house rentals in Berryville have air conditioning?

Absolutely! We offer over 10 house 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.

Are there family-friendly vacation rentals in Berryville?

Berryville has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

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 $120 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 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.

Are there vacation rentals with a dedicated workspace in Berryville?

Yes! Work meets play with ease at over 10 vacation rentals in Berryville featuring dedicated workspaces. Stay connected and productive in your home away from home.

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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Top guest favorite

An outdoor seating area is set in a grassy space, featuring weathered chairs arranged around a stone fire pit. A wooden picnic table is visible, surrounded by lush greenery and trees. The backdrop reveals a scenic view of the rolling hills under a partly cloudy sky.

Cabin in Bluemont

4.99 out of 5 average rating, 560 reviews

Rustic Blue Ridge Cabins

Quaint Rustic Cabin nested at the top of the Blue Ridge Mountains w/detached 150 ft² bedroom Cabin, 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-4 person 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! These are rustic not luxurious Cabins

Top guest favorite

A cozy corner features a cushioned armchair adorned with decorative pillows, next to a small dark wood table with a lamp. A decorative bookshelf holds various books, with warm sunlight illuminating the space. A wooden staircase leads to the upper level.

Home in Winchester

4.98 out of 5 average rating, 206 reviews

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 !

Top guest favorite

A comfortable seating area features a gray sofa positioned against exposed brick walls. A tan upholstered bench serves as a coffee table in front of the couch, while a light accent lamp provides illumination. Hardwood floors add warmth to the space.

Apartment in Winchester

5 out of 5 average rating, 224 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.

Superhost

The loft apartment features rich burgundy walls, a cozy seating area with a green couch, and a wooden dining table. A small kitchen is visible, along with a staircase leading to an upper level. Natural light floods through large windows, highlighting the inviting atmosphere.

Loft in Winchester

4.72 out of 5 average rating, 676 reviews

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!

Top guest favorite

The front porch features two white rocking chairs with red cushions, positioned next to a welcoming red door adorned with a wreath. Lush flowers bloom in a garden bed below, adding color to the inviting entrance.

Home in Winchester

4.97 out of 5 average rating, 263 reviews

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.

Top guest favorite

The exterior of a renovated red brick building is displayed, featuring large windows and a prominent entrance. A decorative cupola is positioned at the roof's peak. Surrounding landscaping includes a small garden area. A sign indicates late checkout time on Sundays.

Guest suite in Summit Point

4.98 out of 5 average rating, 173 reviews

The Big Room - Historic Schoolhouse

Checkout as late as 8pm on Sundays! 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. 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.

Top guest favorite

An open-concept kitchen and living area is presented, featuring modern cabinetry and stainless steel appliances. A cozy armchair with a blue cushion sits beside a small table, while barstools line the kitchen counter. A patterned table adds a splash of color to the space.

Townhouse in Winchester

4.93 out of 5 average rating, 259 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.

Top guest favorite

A charming stone cottage with a wooden front porch features a sloped roof and a brick chimney. Surrounded by trees, the cottage is set on a grassy area, providing a sense of seclusion. Large windows and a welcoming entrance enhance the exterior appeal.

Cottage in Winchester

4.98 out of 5 average rating, 520 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.

Guest favorite

The interior space features a high, wooden-beamed ceiling. A comfortable seating area with an orange couch is visible, along with a workspace area equipped with a chair and desk. Large windows allow natural light to fill the room, and a kitchenette with a granite countertop and shelves is present.

Guesthouse in Round Hill Village

4.97 out of 5 average rating, 466 reviews

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.

Top guest favorite

The historic cottage is framed by lush greenery, featuring a welcoming porch with hanging planters. A dark metal roof complements the light-colored siding, and a gravel pathway leads to the entrance. The structure displays traditional craftsmanship with a covered porch and a well-maintained appearance.

Cottage in Bluemont

5 out of 5 average rating, 138 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.

Top guest favorite

A single-story house is framed by a well-maintained lawn and green trees. A white picket fence encloses the front garden, while a gravel path leads to the welcoming porch. A flowering tree adds a touch of color to the serene environment.

Cottage in Bluemont

5 out of 5 average rating, 245 reviews

Creekside in Bluemont, VA

Creekside is located on a serene 2 acre property in the small town of Bluemont. Many wineries and breweries to visit with just a short drive, river tubing on the Shenandoah River and tons of hiking on the Appalachian Trail. 10 minutes to Purcellville to enjoy the small town, local events and great restaurants. Get ready for your weekend or week long getaway!

Guest favorite

A cozy sleeping area features a spacious bed layered with white and grey bedding, accented by a red throw. Soft lighting from bedside lamps illuminates the natural wood walls, while shelves display decorative items. A flat-screen TV is mounted above the bed.

Guest suite in Stephens City

4.91 out of 5 average rating, 110 reviews

Cozy Cabin

Take it easy at this unique and tranquil getaway. About an hour from D. C. , Luray Caverns, and very close to Historic Downtown Winchester. Take your canoe on the small lake behind the property to joyride or even fish! Shop and get a small town feel in this cozy cabin. If you would like to bring your pet there is a pet fee of $40 that will be added! Thank you

Vacation rentals for every style

Get the amount of space that is right for you

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Homes

Comfortable places with all the essentials

Popular amenities for Berryville vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Berryville

Top guest favorite

The exterior of the studio loft features a red wooden facade with white trim and a steeply pitched roof. Two French doors provide entry, flanked by wooden steps leading to a broad landing. An air conditioning unit is visible on the left side.

Guesthouse in Round Hill Village

4.96 out of 5 average rating, 47 reviews

Wine Country Loft

Guest favorite

A comfortable living area is furnished with a sectional sofa and a classic armchair, complemented by an area rug. Decorative artwork adorns the shelves, and natural light fills the space through large windows, creating a welcoming environment for relaxation.

Home in Berryville

5 out of 5 average rating, 10 reviews

Purple Iris 3b 2b private oasis nr river/mountain

A warm, wood-paneled interior features a kitchen area with a granite countertop and a cozy living space. Comfortable seating is provided by a sofa, and natural light filters in through two windows, illuminating the room and creating a welcoming environment.

Barn in Berryville

4.76 out of 5 average rating, 130 reviews

Modern House Barn on 66 acre Horse Farm

Top guest favorite

A small table with two chairs is set on a wooden deck, showcasing a bouquet of sunflowers and two glasses of red wine. Lush greenery surrounds the area, with glimpses of open lawn and trees in the background under a bright blue sky.

Loft in Charles Town

4.98 out of 5 average rating, 65 reviews

Walnut Glen - Quaint 1 Bedroom Country Get-A-Way

Guest favorite

A vibrant sunset paints the sky in shades of pink and purple, casting a warm glow over the rolling hills. A grassy foreground leads to trees in the distance, creating a serene natural landscape.

Guest suite in Charles Town

4.89 out of 5 average rating, 45 reviews

Hoping to see a Sasquatch?

Guest favorite

A rustic outdoor table is set, featuring two wine glasses alongside a bottle of red wine. A vase with vibrant tulips sits prominently, while a plate holds fresh strawberries and sliced fruit, all set against a backdrop of lush green foliage.

Apartment in Delaplane

5 out of 5 average rating, 6 reviews

Romantic Wine Country Suite | Polo, Hiking Retreat

Guest favorite

The kitchen area features a warm wood design with open shelving displaying plates and glasses. A stainless steel sink is accompanied by a dishwasher and a countertop appliance arrangement, including an air fryer and coffee maker. Soft lighting enhances the inviting layout.

Guesthouse in Lovettsville

4.91 out of 5 average rating, 205 reviews

The Patent House

Top guest favorite

A single-story country home is situated amidst a spacious lawn, bordered by mature trees. The exterior features a combination of brick and siding, with a welcoming entrance. The property exudes a tranquil ambiance, surrounded by the greenery of the landscape.

Home in Winchester

4.96 out of 5 average rating, 67 reviews

Misty Meadow has quite setting in the country.

Quick stats about vacation rentals in Berryville

Total rentals
20 properties
Nightly prices starting at
G$6,275 GYD before taxes and fees
Total number of reviews
490 reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
10 properties include access to wifi

Frequently Asked Questions

Do house rentals in Berryville have air conditioning?
Absolutely! We offer over 10 house 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.
Are there family-friendly vacation rentals in Berryville?
Berryville has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
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 $120 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 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.
Are there vacation rentals with a dedicated workspace in Berryville?
Yes! Work meets play with ease at over 10 vacation rentals in Berryville featuring dedicated workspaces. Stay connected and productive in your home away from home.

Vacation rentals in Berryville

Top-rated vacation rentals in Berryville

Vacation rentals for every style

Popular amenities for Berryville vacation rentals

Other great vacation rentals in Berryville

Quick stats about vacation rentals in Berryville

Total rentals

Nightly prices starting at

Total number of reviews

Family-friendly rentals

Rentals with dedicated workspaces

Wifi availability

Frequently Asked Questions

Destinations to explore