Holiday houses in Rockfish Gap

4.96 out of 5 average rating, 124 reviews

Charming Cottage w/ Majestic Mountain Views

Nestled atop Afton Mountain w/ inspiring views of the Shennandoah Valley, Swannanoa Gatekeeper Cottage is secluded an offers 2 guestrooms w/ a shared bathroom, living room w/ wood fireplace, kitchen, utility room & screened in porch to enjoy the views all 4 seasons. New modern amenities but w/ old world charm. Directly overlooking the intersection of Skyline Drive, Blue Ridge Parkway & Appalachian Trail @ Exit 99 of I-64 near Waynesboro, wineries/breweries, Wintergreen, UVA, hiking, & shopping.

4.92 out of 5 average rating, 581 reviews

Guesthouse in Afton

Spacious Tiny Home Close to Wine, Beer & Mountains

A six-figure tiny home in the epicenter of VA's Brew Ridge Trail. FORBES listed this model as the most beautiful tiny house in the world. "Big Tiny", built in 2017, is a luxurious retreat that is huge on both character and amenities. This handcrafted home boasts a full-sized kitchen private bedroom, cozy sleeping loft, 2 large screen TVs, and full bath with tub. With a cathedral ceiling and walls of windows, this Escape Traveler XL is the flagship offering of the premiere tiny home builder.

4.99 out of 5 average rating, 234 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.

4.98 out of 5 average rating, 115 reviews

Chalet in Afton

Elk Mountain Overlook: Breathtaking Views

Mountaintop overlook with jaw dropping views and camp themed interior design. Perched upon Elk Mountain just off the Blue Ridge Parkway this petite chalet is under 30 min from Charlottesville, 10 min to 151 vineyards/breweries/cideries, and 10 min to Waynesboro. Relax in this natural retreat featuring 2 king bedrooms, 2 person soaker tub, double headed shower, and ample kitchen w/many extras. Take in the views from the large deck, firepit, under porch swing, or mountainside adirondack chairs.

4.97 out of 5 average rating, 181 reviews

Guesthouse in Crozet

Crozet Cottage | Close to Wineries & DT Crozet

Enjoy a cozy getaway at our centrally-located carriage house, in the heart of sought-after Crozet, VA. Completely renovated in 2022, the carriage house feels brand new! Our space offers 1 queen bed and 1 full-bed pull-out couch. The space is .5 miles from downtown Crozet, 2.5 miles to King Family Vineyard and 3.5 miles to Chiles Orchard. It is equipped with a kitchen, a large closet (fits a pack n' play!), high speed internet and Apple TV. We have assigned parking spots in the driveway.

Guest suite in Waynesboro

4.98 out of 5 average rating, 294 reviews

The LoriAnn, A Boutique Stay New Sleep Number Bed

This beautifully restored 1940’s home is located in the City of Waynesboro just a short drive from the Blue Ridge Parkway. Modern amenities, complimentary breakfast items and assurance of comfort awaits! Enjoy one of a kind Autographed Movie and TV Memorabilia. The spacious front porch is all yours including a 100 yr old porch swing that belonged to my Great Grandmother. Along with the Parkway & Skyline Drive, enjoy Restaurants, Breweries, Vineyards, movie theaters and exploring Route 151.

4.99 out of 5 average rating, 192 reviews

Bungalow in Afton

The Bungalow at Afton Mountain Retreat

Welcome to The Bungalow at Afton Mountain Retreat in the heart of Brewery Trail/Route 151, Vineyard country and the foothills of the Blue Ridge Mountains. The Bungalow is located 1/4th mile from Veritas Vineyard. It is within 10 minutes to every brewery, vineyard, distillery and cidery along Route 151 Crozet, 1 mile from the newly opened Blue Ridge Tunnel and 20 minutes to Wintergreen Resort for winter fun! Completely remodeled and ready to spoil the best guests who simply want to unwind.

4.82 out of 5 average rating, 107 reviews

Cozy Mountain Cottage

Welcome to your next mountain cottage getaway. This beauty is located in the heart of Afton, Virginia along route 151 known as "Alcohol Alley". Located 2 miles from Blue Mountain Brewery, 3 miles from Flying Fox Vineyard. A 5-minute drive will bring you to a host of wineries, breweries, and distilleries including Veritas Vineyards, Hazy Mountain Vineyards, and Valley Road Vineyards. We love animals so pets are welcome with a $50 additional fee, per pet. Restaurants can deliver!

4.9 out of 5 average rating, 283 reviews

Cottage in Waynesboro

The Copper Cottage - near the Appalachian Trail

An antique fully renovated, cozy cottage that blends the character of saw milled wood beams, hand-crafted finishes, & local art with the modern comforts of Wi-Fi, Streaming TV, A/C, and a Jetted shower that might raise your attitude with the altitude! At the entrance to Historic Waynesboro (<1 mile) and the riverside park, or its restaurants and stores to entertain even the peculiar palate or collector. Fully fenced in back yard, so bring the pups or the kids to play!

4.98 out of 5 average rating, 192 reviews

Guest suite in Crozet

Guesthouse at Hamilton Oaks

Escape to our guesthouse on a little farmette. This peaceful setting tucked away on several acres along a creek with nature trails is the perfect mountain getaway. We are conveniently situated near quaint wineries, breweries along with hiking and the Blue Ridge Parkway that is a short hop, jump and a skip away. Every effort has been made to keep this a green haven, chemical and synthetic scent free, so you can leave recharged and rested. Non-smoking

4.98 out of 5 average rating, 261 reviews

The Cottage @ Afton Mountain- Close to Wineries!

Welcome to the Cottage at Afton Mountain! Located in the heart of 151 Wine Country, just one minute from Veritas and the Blue Ridge Tunnel. Nestled on a half acre surrounded by woods and a lovely creek, the cottage offers 3 bedrooms, 2.5 baths, a fully equipped kitchen and cozy living room. The Cottage is a wonderful retreat after a day of hiking the Blue Ridge or exploring the surrounding wineries and breweries. We can't wait for you to visit!

4.91 out of 5 average rating, 278 reviews

Bungalow in Waynesboro

Cheerful 2 bd bungalow with HOT TUB! Pet friendly!

Enjoy the entire home to yourself, including a relaxing backyard retreat with hot tub. Perfect for singles or couples who want to stay home and relax or visit the sites then come home to enjoy the hot tub under the stars. 10 min drive to shopping; 10 min to Blue Ridge Parkway & Skyline Drive; 15 min to 151 Breweries. kayaking/canoeing/hiking/fishing on the beautiful South River.

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Other great holiday rentals in Rockfish Gap

Guest suite in Waynesboro

4.9 out of 5 average rating, 10 reviews

Simple Comfort

KristelRating, 5 stars4 days ago

Great place! Host was quick to communicate and provided detailed instructions which made finding the house and getting in easy. Place was clean and the neighborhood is quiet. Would highly recommend.

5 out of 5 average rating, 14 reviews

Home in Waynesboro

New Reno! Central to Skyline, Staunton, Cville

KaitlynRating, 5 stars1 month ago

Reagan’s an amazing host, from booking to the guide book to check in! The house was beautiful and looked exactly like the pictures. Everything was clean and above our expectations! She was super responsive and gave clear instructions for check in/check out! The guide book was very useful in helping us find things to do in the local area! She went above and beyond for a host!

Treehouse in Stanardsville

5 out of 5 average rating, 41 reviews

CloudPointe Retreat

KevinRating, 5 stars1 day ago

This place was awesome the views are incredible and the privacy was like nowhere else. As long as you have 4wd and don’t mind some steps this is a perfect place for couples. Everything was clean and exactly as described. Kevin was even proactive in letting us know the power had went out before we got there and then immediately let us know it was back on. This place really is a hidden gem and you are within 15-30 minutes of restaurants and shopping. We will definitely try to stay here again in the future.

5 out of 5 average rating, 33 reviews

Home in Afton

The Vū, Afton w/ 360º Mountain Views

KristaRating, 5 stars4 weeks ago

We could not have asked for a better stay at the Vū. The home was as beautiful as the photos and the scenic background made it hard to leave. The house is near several vineyards and popular local spots but is set back from the road and neighbors, so felt very private. It’s clear that Emily put careful thought into every detail of the space, from the furniture to the amenities and fully-stocked kitchen. The screened porch was an exceptional feature. I stayed with my family and the space was more than enough to accommodate all of us. I absolutely recommend the Vū for your next mountain getaway!

5 out of 5 average rating, 7 reviews

Cabin in Luray

"The Turtle" Romantic Luxury Cabin in Shenandoah

MichelleRating, 5 stars1 day ago

We had a lovely stay at the cabin. It’s very peaceful and great for a romantic getaway. Morry was also a very responsive host. We had one issue with the building, which he promptly responded to.

4.95 out of 5 average rating, 20 reviews

Loft in Afton

Just Launched! Elegant Stay in Wine Country | UVA

WillRating, 5 stars1 week ago

Elizabeth was a great host and we loved the place we stayed. It was definitely WAY out in the countryside but in terms of convenience to the local wineries/breweries, it was perfect. Also a fairly easy drive to Charlottesville if you wanted to do it for dinner. We will definitely be staying here again!

4.92 out of 5 average rating, 73 reviews

Guesthouse in Waynesboro

Nona's Cottage-Waynesboro/Shenandoah Valley, VA

VermadelRating, 5 stars1 month ago

Have stayed in Nona's Cottage several times -- our favorite Airbnb of all places we travel!