Vacation rentals in Dripping Rock

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Top-rated vacation rentals in Dripping Rock

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

Superhost

Home in Roseland

4.88 out of 5 average rating, 112 reviews

Hiker’s paradise with NEW HOT TUB!

Wintergreen mountain house located yards from the Blue Ridge Parkway & Appalachian Trail! The house is 3 stories with several porches, 3 of them are private. It has a lighted circular driveway. The top floor has two bedrooms & one large bathroom. The main living area is on the second floor with a master bedroom. The bottom floor has another master bedroom, & additional bunk room. The kitchen has a 10-seat kitchen table. After a long day enjoying the outdoors, relax by the fireplace or hot-tub!

Oct 2 – 9

$334 per night
Guest favorite

Cottage in Afton

4.99 out of 5 average rating, 153 reviews

Oasis in the Blue Ridge -Rt. 151 Brew Ridge Trail

Welcome to the Glass Hollow Cottage! Come make yourself at home and enjoy the rustic charm of our custom hand-built cottage. A perfect getaway for a couple or friends who want a 1-of a-kind destination. Adventure and R & R await you!!! Enjoy the well stocked kitchen & the bright, clean, cheery ambience.... everything you need to feel at home & then some. Prime location: Just minutes to Rt. 151/Brew Ridge Trail, dozens of popular wineries/breweries, Wintergreen Resort & Shenandoah Nat. Park.

Sep 20 – 27

$137 per night
Guest favorite

Condo in Wintergreen Resort

4.91 out of 5 average rating, 177 reviews

A True Mountain Getaway! Ski in/Ski out!

Located steps away from the top of the ski slopes at Wintergreen Resort. No snow? No problem! Enjoy the cool mountain breezes, hiking and climbing trails, mountain lakes with beaches, wineries, breweries and much much more. Restaurants and shopping within walking distance. Our place has a galley kitchen and small refrigerator, a large deck to enjoy a quiet dinner and has been newly decorated. There is a king sized bed and a smaller fold out sofa that could accommodate two small children.

Sep 9 – 16

$93 per night

Popular amenities for Dripping Rock vacation rentals

Other great vacation rentals in Dripping Rock

Guest favorite

Cabin in Nellysford

4.97 out of 5 average rating, 158 reviews

Tiny Luxury Retreat: Lake, Hikes, Brews & Vines

Jun 17 – 24

$119 per night
Guest favorite

Condo in Wintergreen Resort

4.98 out of 5 average rating, 169 reviews

Best View in the Blue Ridge from Biscuit's Porch

Jun 12 – 19

$156 per night
Guest favorite

Cottage in Roseland

5.0 out of 5 average rating, 175 reviews

Blue Ridge Cottage - 3 Miles to Wintergreen

Jul 23 – 30

$117 per night
Guest favorite

Home in Stuarts Draft

4.85 out of 5 average rating, 258 reviews

Blackwood Air B & B

Aug 14 – 21

$93 per night
Guest favorite

Condo in Wintergreen Resort

4.97 out of 5 average rating, 230 reviews

Five Minute Walk to Everything!

Aug 31 – Sep 7

$134 per night
Superhost

Condo in Wintergreen Resort

4.9 out of 5 average rating, 101 reviews

All season 3bd/3ba ski out/in - Location & Views!

Jun 14 – 21

$117 per night
Guest favorite

Cottage in Tyro

5.0 out of 5 average rating, 179 reviews

Bear Creek Inn

Mar 10 – 17

$135 per night
Guest favorite

Condo in Wintergreen Resort

5.0 out of 5 average rating, 68 reviews

New Condo! Walk to the slopes 1 bedroom condo

Jun 30 – Jul 7

$93 per night
Superhost

Condo in Wintergreen Resort

4.86 out of 5 average rating, 36 reviews

3min to Ski! Mntn View+Balcony+Fireplace+Roku+Hike

Apr 23 – 30

$90 per night
Guest favorite

Condo in Wintergreen Resort

4.99 out of 5 average rating, 81 reviews

2-3 min drive to slopes, stair-free/free firewood!

Apr 9 – 16

$89 per night
Superhost

Home in Wintergreen Resort

4.84 out of 5 average rating, 19 reviews

Mountain Retreat: 4 Kings+Brewery+Winery+Ski+Hike

Sep 5 – 12

$303 per night
Guest favorite

Cabin in Wintergreen Resort

5.0 out of 5 average rating, 21 reviews

Firepit, EV charger, Modern Renovated Home

Apr 21 – 26

$123 per night

Destinations to explore

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  5. Dripping Rock