Holiday rentals 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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Superhost

Home in McGaheysville

4.84 out of 5 average rating, 121 reviews

Spring Escape Near Massanutten Adventures & Trails

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

4.95 out of 5 average rating, 184 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, 374 reviews

Romantic Cozy Cabin Firepit Fireplace Fast Wi-Fi

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.

Superhost

Flat in McGaheysville

4.84 out of 5 average rating, 251 reviews

Massanutten Cozy Condo with Hot Tub & Jacuzzi

Luxury Apartment ideal for families with little kids in Massanutten. There is a huge deck with private 5-person Hot Tub and small playground on it. It is located only 5 minutes away from the ski lodge, go karts, bumping cars, Mini Golf.The Campfire Grill Restaurant is only 2 minutes away. The indoor and outdoor Water park is 8 minutes away. A gorgeous and spacious retreat in the best location for skiing/snowboarding, exploring the resort, hiking, relaxing, and enjoying the fresh mountain air.

Superhost

Cabin in Crozet

4.86 out of 5 average rating, 101 reviews

#4 Cabin Near Wineries, Breweries, UVA, & Hiking

The #4 Loblolly Cottage is an eco-friendly cabin overlooking a lake. Small 450 sq ft, cottage has a queen size bed in the primary bedroom, bunk beds in the second bedroom and a full size futon in living room. Kitchenette equipped with modern appliances and breakfast table. Bathroom and shower. Wi-Fi. Private porch. Pets are welcome for an additional fee. Hike, canoe, fish and bike onsite on a 129 acres. Close by wineries, 15 min to Shenandoah National Park. This cabin is ideal for families!

Guest favourite

Cabin in Stanley

4.97 out of 5 average rating, 182 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!

Superhost

Cabin in Shenandoah

4.79 out of 5 average rating, 464 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

Cabin in Afton

4.97 out of 5 average rating, 202 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

Apartment in Wintergreen Resort

4.94 out of 5 average rating, 132 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

4.91 out of 5 average rating, 150 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, 184 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

Chalet in Brightwood

4.96 out of 5 average rating, 141 reviews

Charming Chalet in Blue Ridge Wine Country

NEW! PICKLEBALL/BASKETBALL COURT PUTT PUTT GOLF Sunset Ridge is in the heart of all you want to do! Newlyweds to families, everyone will love it here! The peace and quiet of the country, or the excitement of exploring new and different places, all await you! Check out our guidebook for local attractions, restaurants, nightlife, and sightseeing. Enjoy the serenity of the country! Follow us: @sunsetridgechalet