Holiday rentals in Clarke County

4.95 out of 5 average rating, 303 reviews

Flat in Bluemont

A Great Getaway — Foxglove Retreat

Nestled in the Blue Ridge Mountains, "Foxglove Retreat" offers you complete privacy and beautiful vista views of the Shenandoah Valley. Equipped with all the necessities for a relaxed and luxurious experience, the "Foxglove Retreat" is sure to become one of your favorite destinations. "Foxglove Retreat" is ideally located near popular tourist destinations, restaurants and wineries. The Bears Den Trail Center is walking distance for those who would like to explore the beauty of the Blue Ridge Mountains on foot. For those who seek nearby shopping and sightseeing, the quaint village of Middleburg is to the southeast and has many antique shops and elegant boutiques nestled in its historic buildings. To the east is the town of Leesburg featuring the upscale Leesburg Corner Premium Outlets and the Leesburg Farmers’ Market. To the west is the Old Town of Winchester where you will discover charming shops, restaurants, galleries, centuries-old architecture, and historical landmarks.

4.87 out of 5 average rating, 229 reviews

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.

4.98 out of 5 average rating, 111 reviews

Cottage in Boyce

Pets? YES! Hot Tub | Fast Wi-Fi | Fire Pit

Moonflower Cottage is a historical farmhouse nestled on two rolling acres in Virginia's wine country. Visit the area's top vineyards, dining, and antique shops. Float down the Shenandoah River. Cap your day sipping cabernet as the sun sets and the cottage blooms like the moonflowers that grow wildly. Bathe in the warm glow of string lights under the grapevine arbor or enjoy a relaxing soak in the spa. Young or old, you are sure to find the vintage that you are looking for at Moonflower Cottage.

Guest suite in Summit Point

4.98 out of 5 average rating, 166 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!

5 out of 5 average rating, 54 reviews

The Hill House at Stubblefield

Enjoy spectacular views of the Blue Ridge from this meticulously crafted stone house. The Hill House is situated on 40 acres in beautiful Clarke County, Virginia, and offers easy access to any outdoor activity your heart desires. This getaway is 2 miles from a public boat landing, and is surrounded by pastoral views and country roads in all directions. The Hill House is on Stubblefield Farm, which has its origins dating back to 1792. Come enjoy local wineries, breweries, and antique shops.

4.97 out of 5 average rating, 199 reviews

Home in Winchester

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!

4.99 out of 5 average rating, 79 reviews

Deer Chase

Welcome to our renovated cabin, “Deer Chase”, incredibly convenient to Clarke County's Ruritan Fairgrounds, Rosemont Manor, wineries, breweries, Appalachian Trail, and more. This is just off Rte 7, located between Loudoun and Frederick Counties, less than 10 minutes to 81, in a private and relaxing setting. Looking for convenience to local amenities, in town for a wedding, Lucketts Fair, or Apple Blossom Festival, or just passing through and just need to kick your feet up, you found it.

Superhost

Cottage in Paris

4.91 out of 5 average rating, 106 reviews

Quaint cottage in historical town of Paris VA!

Welcome to my home! This house was built in the 1820’s in the historical town of Paris, Virginia! With lots of history and character this house still has some of the original exposed beams and hardwood flooring! If you enjoy the outdoors, wineries, breweries, and shopping this is a perfect location for your stay! Minutes from the Appalachian trail, and Sky Meadows park there’s plenty of hiking around. Famous Ashby Inn restaurant just a short walk away and many more amazing places!

4.94 out of 5 average rating, 214 reviews

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!

4.96 out of 5 average rating, 213 reviews

Cottage in Bluemont

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.

4.94 out of 5 average rating, 155 reviews

Cabin in Upperville

Island cabin

Getaway from the city and escape to the countryside in this beautiful cabin recently renovated. Situated on a beautiful private lake, enjoy your morning coffee on the porch over looking the water, or enjoy the fire pit with the sunset. The cabin features a queen size bed, a full bathroom, a kitchenette, and a cozy living room area. There is also an outside grill and fire pit. We recently updated the kitchen and added a full size fridge/freezer.

4.97 out of 5 average rating, 233 reviews

Home in Winchester

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.

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Popular amenities for Clarke County holiday rentals

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Pool

Free parking on premises

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Other great holiday rentals in Clarke County

Superhost

Cabin in Front Royal

4.92 out of 5 average rating, 49 reviews

Skyline Shenandoah! Hot Tub DogOK EV Charger Grill

KatherineRating, 5 stars1 day ago

quick note on the bathroom. The towel hanger is a bit wonky falls off the wall if the grab the towel the wrong way

Home in Bluemont

4.86 out of 5 average rating, 36 reviews

Cozy Bluemont Haven

MarkRating, 5 stars3 weeks ago

Great little cabin up a hillside and in a wooded area. It was clean, comfortable and had a nice outdoor deck for lounging. Good choice if you’re looking for a peaceful escape.

5 out of 5 average rating, 6 reviews

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

MeaganRating, 5 stars8 months ago

My sister was visiting from Canada so we decided to head to Virginia to hit some wineries and breweries. We had a lovely stay at Elizabeth’s place! It looked just like the photos, was clean and cozy, and a perfect place to unwind at the end of the night with a glass of wine. The hosts texted us recommendations of stuff to do in the area and we had an amazing time. Great couch and TV set up, very comfortable beds, and beautiful wooded surroundings. Highly recommend for any trip to the area!

Barn in Berryville

4.78 out of 5 average rating, 120 reviews

Modern House Barn on 66 acre Horse Farm

LisaRating, 5 stars2 months ago

This place is tucked into a little peace of heaven. Very peaceful and easy to get to. The interior is nicely designed, furnishings are comfortable. The kitchen has a little eat in area with plenty of space to sit and chat, eat, play board games, or cook. I loved that the bedrooms were upstairs so if someone wanted to sleep, it’s quiet enough to do that. The upstairs is quite sound proof. There’s also a nice little tv area upstairs between the two rooms. The rooms have plenty of space to store clothes if you are staying longer. The outside area also has a picnic table and grill which would be nice when staying in the warmer months. The hosts were very kind and responsive. They answered any questions we had quickly. I highly recommend this place and hope to stay again when we come back.

4.98 out of 5 average rating, 49 reviews

Loft in Charles Town

Quaint 1 Bedroom Country Get-A-Way

KellyRating, 5 stars1 week ago

Probably the best Airbnb we’ve visited! The space has everything you need, well thought out for guests, spotless in terms of cleanliness, a few games to enjoy, the kitchen was great with a good-size small fridge, and the outdoor space- what a treat! Deck and fire pit spaces were great for relaxing, watching the abundance of deer in the area, and enjoying the quiet. The location was great for exploring nearby attractions. The hosts were very friendly, welcoming, and kind!

4.95 out of 5 average rating, 63 reviews

Cabin in Front Royal

The Cozy Bear Cabin | Hot Tub, Fenced Yard, Games

AnnRating, 5 stars3 weeks ago

Matt's place was beyond expectations. It was so cozy and the bear decor everywhere was so cute! We had everything we needed and then some. the kitchen is beautiful and we enjoyed the serene back porch. The fenced in yard was a major bonus for our pup to enjoy the nature as well. We didn't get a chance to enjoy the grill area as it was raining most of our trip but that would have been a great place to enjoy our dinners. The theater and game room were awesome too. We had one mishap with the propane company locking the propane, so we couldn't use the gas stove and no one could come out to fix it since it was a holiday weekend. Matt immediately remedied the situation by instacarting us an electric 2 burner stove (you're welcome to any future guests that need it😀) . I would definitely recommend Matt and Matt's place and will stay again if ever in the area. Thank you so much for making our vacay great!

4.89 out of 5 average rating, 9 reviews

Home in Boyce

The Ladybug Retreat

EmilyRating, 5 stars3 weeks ago

We really enjoyed our stay at Ladybug Retreat! It was perfect for our family of six. The home was spotless and exactly as described in the listing. The property itself was beautiful and relaxing—we saw several deer grazing in the yard, a couple of groundhogs, and even a bluebird that liked to perch on the glass door handle. We would absolutely stay here again and highly recommend it to anyone looking for a comfortable and welcoming place to stay!