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Holiday houses in Charlottesville

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Top-rated holiday rentals in Charlottesville

Guests agree: these stays are highly rated for location, cleanliness and more.

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Cabin in Stanley

4.88 out of 5 average rating, 185 reviews

Ironside Ridge at Skyline Lakes

Modern Nordic style/themed cabin located on 2+ wooded acres with an outdoor fire pit, BBQ grill area, wrap around deck & High Speed Starlink Internet. Fully stocked kitchen, wood burning stove, firewood included, with large bedroom and open floor plan. Incredible hiking from the cabin: SNP, Big Meadows, Appalachian Trail, waterfalls, and more. Nearby fishing pond. Pets and children allowed. Leave the stress of life behind and come relax at Ironside Ridge. Superhost with 750+ Five Star reviews.

Guest favourite

Home in McGaheysville

4.85 out of 5 average rating, 117 reviews

Winter Retreat Near Skiing & Massanutten Fun

Breathe the mountain air of the Shenandoah Valley! Relax in our lovely home and enjoy the Massanutten Resort and Shenandoah Park. Our prime location is 5 min from hiking, adventure park, water park, horseback riding, golf course, mini golf, skiing and tubing, spa, and bumper cars. 15 min to Skyline Drive, 15 min to Shenandoah River Enjoy nearby wineries, farms, caverns. *High-speed internet, streaming services, fully equipped kitchens, and comfortable bedding. **Driveway is very steep**

Guest favourite

Home in Elkton

4.94 out of 5 average rating, 172 reviews

Hottub 5 acres, Great hiking,The best views around

Stony Creek Lookout is a one-of-a-kind luxury retreat perched in the serene seclusion of the mountains.Brand new complete renovation, modern amenities, hot tub, sizable elevated deck, video/board games, theatre room, kayaks and high quality furnishings !This extraordinary stay adjoins the Shenandoah NatlPark with the best views in the Shenandoah Valley, hike out your back door. Pet friendly, 5 min from Massanutten 4 season resort, Shenandoah River & much more. Great Wifi & cell service! 5 TVs

Guest favourite

Cabin in Shenandoah

4.92 out of 5 average rating, 367 reviews

Romantic Shenandoah Mountain Retreat

Embrace the endless beauty of the Shenandoah Valley from this private mountain retreat with stunning sunset views and endless stars. Enjoy the community's private access to the Shenandoah River. Escape the city, but still have access to our modern comforts of cell phone service and WIFI. Relax in front of the wood-burning fireplace. or just enjoy reading a book on the swing in the screened porch. Our property has one security camera and noise monitoring at the entry area of the front door.

Guest favourite

Cabin in Stanley

4.98 out of 5 average rating, 174 reviews

Stunning Mountain Views in Luxurious Log Home!

Perfect for couples or families wanting STUNNING MOUNTAIN VIEWS (from the cabin & from the hot tub) in the ideal location. Romantic, luxurious & immaculately clean custom cabin, fully equipped w/all pine interior. Super close to Shen Natl Park/Skyline Drive, Luray Caverns, unique shops & markets, restaurants, horseback riding, fishing, golf, wineries/breweries, historic sites, Shenandoah River, Lake Arrowhead & the slopes of Massanutten Resort! Find us at LURAY MOUNTAIN CABINS for SPECIALS!

Cabin in Shenandoah

4.78 out of 5 average rating, 451 reviews

Shenandoah Sunsets~Breathtaking Views~ New Hot Tub

*Weekends fill fast, but we have great weekday rates! --Breathtaking mountain top cabin with private river access • 180 degree sunset views from 4 decks • Minutes from downtown Luray & Massanutten Resort • Backs to 400 acres of private woodlands • Fully equipped & stocked kitchen • Gas Fireplace • Grill • Onsite washer & dryer • Queen sofa bed • Foosball table • Satellite internet • Smart TVs • Paved driveway • Extensive DVD collection + games • Come feel the amazing mountain top breezes

Guest favourite

Home in McGaheysville

4.79 out of 5 average rating, 126 reviews

Paradise Resort at Massanutten

Paradise on the mountain top. A Massanutten, VA location, a country feel with modern style. Located inside Massanutten Village about a mile from the gated entrance into the Massanutten Resort. Sun room with view of the surrounding mountain. Relax as you take in the scenery. Don’t forget a day trip or half day trip on beautiful Skyline drive. Outdoor swimming pool available during the summer. Small family reunions, Corporate work-groups needing extended stays, ALL WELCOMED!!

Guest favourite

Cabin in Afton

4.97 out of 5 average rating, 193 reviews

Inn at the Woods: Updated Cabin w/Mountain Views

Fall in love with the charm of this recently updated ‘Hansel & Gretel’ style cabin located on Castle Rock Mountain. This cabin has 3 bedrooms + a loft, with a total of 4 queen beds. Hike and explore the 20+ acres or relax on the large multi-tiered deck and fire-pit area while soaking in the mountain sunsets. Enjoy nearby dining, breweries, or wineries, the historical town of Charlottesville, or spa, golf, tennis, and skiing at the Wintergreen Resort - both just a short drive away.

Guest favourite

Condo in Wintergreen Resort

4.93 out of 5 average rating, 122 reviews

BlueRidge Getaway- Dog Friendly

Relax and enjoy spectacular top-floor mountain views from the deck. This recently renovated unit is at the top of the mountain close to many hiking trails. Visit the Wintergreen village, with its restaurants and shops, with a 5 minute drive or an easy hike through the woods. You also have access to Rhodes Farm and Chestnut Hills pool. This condo is convenient to Devils Backbone, Bold Rock, and the litany of other breweries, cideries, distilleries, and restaurants. Dogs welcome!

Guest favourite

Home in McGaheysville

4.92 out of 5 average rating, 138 reviews

Pleasant Place near Massanutten Resort!

Located near Massanutten Four Season Resort, Pleasant Place offers everything you need for a comfortable stay. Whether you are looking for a weekend getaway or new views for your telework station, this property has it all. With an abundance of light, an outdoor firepit, and full deck dining, you are sure to get some much-needed relaxation in the mountains. Minutes away from Massanutten Ski Lodge, two 18-hole golf courses, year round indoor/outdoor water park, and more!

Guest favourite

Cottage in Shenandoah

4.96 out of 5 average rating, 178 reviews

Cozy Cottage Retreat: SNP, Luray Caverns, River

Clean & cozy cottage conveniently located in the town of Shenandoah. Guest love the central location to Shenandoah National Park via Elkton Swift Run (12 miles) or Luray Thornton Gap (28 miles), Luray Caverns (15 mi), Massanutten Resort (9 mi), and a short drive to local colleges like JMU, EMU, and Bridgewater College. Walking distance to Shenandoah River, a public boat landing, local stores and small parks. Please check out our reviews to see what guest have to say.

Guest favourite

Cottage in Crozet

4.88 out of 5 average rating, 244 reviews

A-Frame Pawpaw 2 BR Cabin, Lake, Hike & Canoe

Eco-friendly cottage overlooks lake in mountains 1 BD w/ queen, ladder to sleeping loft w/ two twins, double futon in living-room. Bath with tub. Deck with charcoal grill. Only a few yards from water’s edge. Onsite walking trails with mountain bikes, canoes, and fishing. Family friendly! Pets welcome with additional $50 fee for the first pet, $25 for an additional pet. Wi-Fi in this cottage sometimes needs owner to reset. Near the Shenandoah National Park!

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Popular amenities for Charlottesville holiday rentals

Free parking on premises

Air conditioning

Stay near Charlottesville's top sights

UVA University Hospital21 locals recommend

Monticello634 locals recommend

Downtown Mall291 locals recommend

University of Virginia251 locals recommend

John Paul Jones Arena60 locals recommend

Mas160 locals recommend

Other great holiday rentals in Charlottesville

Guest favourite

Home in Charlottesville

5 out of 5 average rating, 20 reviews

Casa Crozet

Guest favourite

Home in McGaheysville

4.81 out of 5 average rating, 26 reviews

Altitude Adjustment Awaits!

Guest favourite

Home in McGaheysville

4.96 out of 5 average rating, 50 reviews

In Resort- Family fun- Kids Suite-Game Room

Condo in Wintergreen Resort

4.88 out of 5 average rating, 159 reviews

Wander Lodge: Golf, Spa, Wine, or just a getaway

Guest favourite

Barn in North Garden

4.91 out of 5 average rating, 148 reviews

Mountain Views & Hot tub! Close to UVA - Pets OK

Guest favourite

Home in Nellysford

5 out of 5 average rating, 13 reviews

Foxy Retreat Stoney Creek/ Wintergreen Golf/ Ski

Guest favourite

Condo in Wintergreen Resort

4.98 out of 5 average rating, 124 reviews

Slope side+Panoramic Mountain Views!

Cabin in Gordonsville

4.75 out of 5 average rating, 4 reviews

YURIT / CABIN Rental Available with Amenity

Quick stats about holiday rentals in Charlottesville

Total rentals
970 properties
Total number of reviews
62K reviews
Family-friendly rentals
520 properties are a good fit for families
Pet-friendly rentals
290 properties allow pets
Rentals with a pool
40 properties have a pool
Rentals with dedicated workspaces
510 properties have a dedicated workspace

Destinations to explore