Holiday rentals in Dripping Rock

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Top-rated holiday rentals in Dripping Rock

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Superhost

Apartment in Wintergreen Resort

4.78 out of 5 average rating, 69 reviews

Wintergreen Best location,Arcades,king bed,2 room

Enjoy this beautifull newly renovated condo in the 18th hole of wintergreen resort entirely to yourself, cozy, centrally located dont miss this unique stay, within minutes of the slopes. Be pampered with a morning Coffee or hot cocoa in the new granite kitchen with new appliances and relax in the amazing view in the terrace peaceful, surrounded with trees and birds. Sleep really well with all new memory foam mattress, central a/c, heating, fully equipped, 2 Smart Tvs and 2 Arcades NBA and Pacman

Top guest favourite

Cottage in Covesville

5 out of 5 average rating, 116 reviews

Historic cottage with stunning mountain views

Welcome to Rose Cottage in picturesque Albemarle County, where you'll enjoy expansive 360-degree views of the mountains surrounding historic Cove Lawn Farm. Relax in the tranquil rural setting or stroll more than two miles of comfortable walking paths that wind through 25 acres of stream-lined hayfields. From Rose Cottage, you're just minutes from the best local cideries, distilleries, and wineries including Pippin Hill Farm & Vineyards. Easy 20-minute drive to UVa and 22 minutes to Monticello.

Top guest favourite

Villa in Wintergreen Resort

4.96 out of 5 average rating, 76 reviews

NO STEP ENTRY Wintergreen Mtn Home,HotTub,Sleeps10

We had to create a new listing for this property. Previous listing had 70+ reviews with a 4.8 Star rating. Same great host and same great house, just a new listing. Screenshots of old listing in additional photos. Stay at this luxurious 4-bedroom, 3-full bath vacation rental home for 10 in Wintergreen, within minutes of top-notch golf courses, skiing / snow boarding at the Mountain Inn, and dozens of hiking trails . In addition to the unbeatable location, the property offers a private hot tub!

Guest favourite

Home in Roseland

5 out of 5 average rating, 13 reviews

Hot Tub! Wintergreen Resort!

Check out our 5 star reviews on VRBO and "cozy cabin at wintergreen dot com". Prepare to escape and relax at our three bedroom, two bath cabin, nestled atop the Blue Ridge mountains, a short walk (5 Houses) to the Devils Knob Overlook. This luxury resort retreat is perfect for couples getaway, wedding, family vacation or girls weekend. Spend the day brewery hopping down the famous Route 151, where you have over twelve wineries and breweries to visit. Or enjoy hiking, skiing, spa & golfing.

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!

Superhost

Apartment in Wintergreen Resort

4.88 out of 5 average rating, 163 reviews

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

Comfortable 3-BR, 2-bath condo on Devil's Knob Golf Course. Comfortably sleeps 6-7, 2 Queen beds, 1 full bed, futon, & comfy couch. Woodburning fireplace; balcony, small newly renovated kitchen w/stove, dishwasher, microwave, Keurig, tea kettle,coffee maker, crockpot; Smart TV w/ Streaming apps(free only); Walking distance to hiking trails, nature center, DeVine Wine & Coffee shop, tennis facilities, & the lovely wintergreen spa; less than 1 mile from Mountain Inn & restaurants & shops.

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!

Top guest favourite

Home in Charlottesville

5 out of 5 average rating, 72 reviews

Charming 3 bed/3 bath cottage centrally located

Nestled in a quiet neighborhood in central Charlottesville, this charming 3 bedroom home is conveniently located just minutes away from UVA and the historic downtown mall. This bright, spacious 1930s home has been newly renovated and features a fully equipped kitchen, multiple living spaces, a dining area, and a private deck for outdoor enjoyment. Each of the 3 bedrooms features an updated full ensuite bathroom, and a washer and dryer are provided for your convenience.

Guest favourite

Home in Wintergreen Resort

4.93 out of 5 average rating, 61 reviews

Hot Tub Mntn Views Pool Tennis Golf Hiking 52"HDTV

Impressive 3-story mountain estate. Ideal for family retreats and adventurous getaways. Features HOT TUB. Wineries, breweries, farmers market, and walk to hiking trails. 4min dive to slopes! ★Comfortably sleeps 10: K, K, Full, Twin bunk beds, Sleeper sofa in loft ★Great room with stone fireplace ★Dining table for 8 ★FAST Wi-Fi ★Two 52" HDTVs ★Wrap around decks ★Fire Pit ★Hot Tub ★Plenty of parking Seasonal outdoor pool/tennis access. Resort access not included.

Top guest favourite

Home in Wintergreen Resort

5 out of 5 average rating, 27 reviews

5-star Luxury 4BR/4BA Lodge w/ HotTub!

Rustic, 5-star lodge great for a Guys or Gals weekend, weddings and family gatherings. Well-appointed with 4 cozy bedrooms each with their own private en suite bathroom. Unleash your inner chef in the gourmet kitchen w/ sun-filled dining area. Spread out in the 2-story family room with gas fireplace. Head outside to the expansive deck overlooking the 14th hole on Devils Knob golf course and enjoy the hot tub and firepit.

Guest favourite

Home in Wintergreen Resort

4.98 out of 5 average rating, 47 reviews

Super Comfy Mtn Escape w/ 4 Bedrooms & Hot Tub

Bring the whole family or group of friends to this awesome, comfortable home with lots of room for fun; a brand new hot-tub and huge patio; plenty of parking/two-car garage; and central location for epic views, hikes, and skiing. Two master bedrooms on each end with king size beds. One bedroom with a queen and another with two twin beds and a crib make it a perfect place for multiple families.