Places to stay in Berryville

4.87 out of 5 average rating, 229 reviews

The spacious living area features a high, wooden ceiling and a stone fireplace as a focal point. A comfortable beige sectional sofa invites relaxation, while windows allow natural light to fill the room. Neutral tones complement the rustic wooden walls, creating a warm atmosphere.

Home in Bluemont

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.

4.99 out of 5 average rating, 542 reviews

Three cartons of eggs are displayed, featuring a variety of colors including shades of brown and green. The eggs are neatly organized, showcasing a mix of sizes and hues against a textured wooden surface.

Cabin in Bluemont

Rustic Blue Ridge Cabin

A quaint rustic cabin nested at the top of the Blue Ridge Mountains, with a detached 150 ft² bedroom, 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- 4person 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!This is a rustic not luxurious cabin!

4.99 out of 5 average rating, 109 reviews

Farm stay in Bluemont

Welcome to the Hidden Hive!

The Hidden Hive is located on beautiful, tranquil farmland, within a few minutes of Loudoun County’s premiere wineries and breweries. Rest your head here after a hard day’s hike on the Appalachian Trail or a celebratory evening at a Bluemont wedding. We are a hobby farm and own chickens, goats, dogs, and barn kitties. Wildlife such as deer can be seen, and owls heard here at night. You may see cyclists or horseback riders pass along our historic Civil War roads. We can’t wait to host you!

5 out of 5 average rating, 208 reviews

A historic archway welcomes visitors to Old Town Winchester, illuminated by streetlights through gently falling snow. Snow covers the ground, leading down a pathway lined with trees. Buildings with traditional architecture and a mix of shops can be seen on either side.

Apartment 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.

Superhost

A warm-toned living area features a staircase leading to an upper level. The kitchen area is visible in the background, equipped with cabinets and appliances. A wooden dining table sits in the foreground, complemented by a cozy seating area with a patterned couch.

Loft in Winchester

4.73 out of 5 average rating, 657 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!

A set of wooden shelves mounted on a light blue wall displays a cozy gray blanket, a decorative basket, and a small potted plant. A framed sign with a welcoming message is positioned above the items, adding a personal touch to the space.

4.97 out of 5 average rating, 254 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.

Farm stay in Round Hill Village

Two young goats are seen playfully interacting near a wooden structure. One goat has a predominantly white coat with light brown markings, while the other displays a black and white pattern. Natural earth and straw are present on the ground, emphasizing the outdoor setting.

4.93 out of 5 average rating, 412 reviews

The Goat Loft - A Private, Peaceful Getaway!

Private Blue Ridge Retreat – Nature, Hiking, and Relaxation Escape to 13 acres of peaceful woodlands and pasture at the base of the Blue Ridge Mountains. Enjoy the goats from the private deck, perfect for stargazing at night! Nearby, hiking on the Appalachian Trail, cycle scenic routes, or explore historic towns, wineries, and breweries. The Potomac and Shenandoah Rivers offer even more outdoor adventures. A perfect mix of tranquility and adventure, but just minutes from everything!

4.94 out of 5 average rating, 214 reviews

An A-frame cabin is nestled among the trees, featuring a metal roof and large windows that reflect the warm glow of interior lights. A spacious deck includes a dining table and lounge seating, surrounded by string lights, providing an inviting outdoor space.

Cabin in Front Royal

The Wizard's Chalet • Cozy nature escape • Hot Tub

Looking for a fun getaway in a relaxing, secluded spot? Come visit The Wizard's Chalet, a cozy & upgraded cabin located in the Shenandoah Valley just one mile from Shenandoah River access and a few miles from restaurants, wineries, basketball & volleyball courts, and more! With a fully stocked kitchen, three cozy bedrooms, high speed WIFI, hot tub, and several beautiful outdoor gathering spaces, this magical cabin is perfect for couples, friends, or the entire family!

4.93 out of 5 average rating, 243 reviews

A welcoming entrance to Old Town Winchester is showcased, featuring a prominent archway with the text 'Old Town Winchester.' Lively shops and cafes line the pedestrian mall, which is adorned with trees and outdoor seating beneath umbrellas.

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.

A hot tub is situated on a paved area surrounded by stone, featuring a textured design. The tub is covered with a black lid, offering an appealing contrast to the greenery of the yard. A grill is partially visible underneath a protective cover nearby.

4.97 out of 5 average rating, 233 reviews

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.

4.97 out of 5 average rating, 498 reviews

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

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.

Guesthouse in Round Hill Village

The exterior of the carriage house features a wooden façade with a green metal roof, framed by lush greenery. A brick walkway leads to a welcoming entry door, complemented by potted plants at the entrance. Windows allow natural light into the space.

4.97 out of 5 average rating, 452 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.

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Other great vacation rentals in Berryville

Apartment in Round Hill Village

A spacious bedroom is presented, featuring a king-size bed covered with a black and white patterned quilt and flanked by two wooden nightstands. A dark upholstered bench is placed at the foot of the bed, and a light-colored area rug lies beneath, adding texture to the floor.

5 out of 5 average rating, 67 reviews

Whole Garage Apartment with Blue Ridge Views

DianaRating, 5 stars1 week ago

Our second stay here. Just as good as the first. We met our family most every day (15 minutes away) and got to participate in their many activities, and yet have a quiet, clean, large space to retreat to. They were so flexible that we felt like family !

Superhost

Home in Harpers Ferry

5 out of 5 average rating, 3 reviews

Gorgeous cabin on Blue Ridge

JamieRating, 5 stars5 days ago

We had a wonderful weekend in this sweet cabin! From before check in, until check out Flora made the whole experience easy and comfortable. There are so many thoughtful details throughout this property. Super clean and beautiful inside, but we spent most of our time enjoying the incredible deck. Our favorite part was that we could still sit outside in comfy seats and watch a thunderstorm while covered! Close to lots, but far from it all. We can’t wait to come back!

Guesthouse in Round Hill Village

A compact black device is positioned on a light-colored countertop near a window. The device displays signal strength indicators on a small screen. A wall outlet is visible in the background with a charging unit connected.

5 out of 5 average rating, 13 reviews

The Cottage

NelloRating, 5 stars1 month ago

My girlfriend, our dog, and I stayed for over 30 days at this peaceful spot on Paxon Road in Round Hill, and it was exactly what we were looking for. The property is quiet, secluded, and surrounded by nature Wildlife wandered nearby and was totally unbothered by us or our dog. We loved being so close to a bunch of great wineries and breweries, too. The host was very responsive and made the whole stay easy. Highly recommend for anyone looking for a calm, nature-filled getaway.

4.98 out of 5 average rating, 80 reviews

The two-story house features a spacious deck constructed of light wood, supported by stone pillars. Multiple steps lead up to the deck, which is surrounded by trees, creating a natural and private setting. Canoes are visible stored beneath the deck.

Home in Bluemont

The River House

AlanaRating, 5 stars3 weeks ago

My husband and I were looking for a place that our family could relax and make memories for our wedding weekend. Janell and Bruce’s home offered just that. They were wonderful hosts - they were responsive, the place was beautifully kept, and they even gave us an early check-in so my family could get settled. The porch and kitchen are fantastic and gave us a chance to have a nice family barbecue to kick off our wedding weekend festivities. We highly recommend to anyone looking for a peaceful escape with modern amenities and super gracious hosts!

A pair of white appliances are positioned side by side, featuring a washing machine on the right and a dryer on the left. Both machines have clear control panels displaying various settings and dials, set against a neutral wall.

4.95 out of 5 average rating, 58 reviews

Misty Meadow has quite setting in the country.

KerinaRating, 5 starstoday

This is the second time staying in this beautiful home. Marie has everything you need for a perfect stay. The area is so beautiful and the home is soooo cozy. We will definitely be back.

Cottage in Round Hill Village

The exterior of the charming cottage is displayed, featuring a green metal roof and a welcoming porch with rocking chairs. Lush green grass surrounds the property, while vineyards are visible in the background. A bright sun sets, casting a warm glow over the scene.

4.98 out of 5 average rating, 62 reviews

Farm winery cottage with mountain & vineyard views

MaryRating, 5 stars2 weeks ago

WOW!!! This is THE gem of air bnb’s. I cannot begin to articulate just how incredible it was. The photos don’t give justice to how beautiful this home is and how thoughtful all the details are. Luanne was amazing and communicative- her and her husband truly went above and beyond in hospitality and kindness when we forgot bug spray and charcoal, and when asking where we could find some locally they grabbed some for us! The site is breathtaking, we loved sitting by the fire pit and looking at the stars after a night of grilling. 1 night was rainy and still so enjoyable because their kitchen was fully stocked with any and all utensils needed to make a lovely meal and admire the storm over the mountains from the beautiful covered back deck! Little details like super comfy robes and slippers made me feel right at home. The winery is so cute and has delicious wines- we had a flight of both the red and white and would definitely recommend! Truly cannot wait to come back, definitely plan to!

4.95 out of 5 average rating, 40 reviews

Cabin in Historic Old Town Winchester

StephanieRating, 5 stars3 weeks ago

We loved the character and unique flow of the house. It had everything we needed and was very clean and well put together. The whole neighborhood has a lot of charm and it is an easy and quick walk to the downtown shops and restaurants. We would definitely stay here again!