Holiday rentals in Rockfish Gap

4.96 out of 5 average rating, 126 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, 582 reviews

Guest house 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, 235 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, 116 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.

Guest suite in Waynesboro

4.98 out of 5 average rating, 296 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, 194 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.

4.99 out of 5 average rating, 181 reviews

Treehouse in Verona

The Laurel Hill Treehouse

Fully immerse yourself in nature in this serene Scandinavian-inspired woodland retreat, ideal for a couple's getaway. The treehouse is perfectly nestled amongst the trees, offering a chance to unwind while enjoying the beautiful views of nature. Just imagine yourself relaxing on the wrap around porch, soaking in the hot tub, cooling off in the creek, & cozying up to a crackling fire. We invite you to unwind, reconnect with nature & create cherished memories in this tranquil hideaway.

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, 194 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, 285 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

4.96 out of 5 average rating, 77 reviews

Farm stay in Elkton

Duck Inn B&B at Small Axe Farms - no cleaning fee

ClaireRating, 5 stars1 day ago

This AirBNB is perfect for a peaceful stop on a long road trip! We got a wonderful, tasty dinner and then sat outside to watch a beautiful sunset with the sheep and dogs. Lots of games and activities for when it got dark (love a good Jenga match!) . Great for stargazing as well! The bed was so comfortable and everything felt very clean. Great shower too! Thank you for making our first stay in Shenandoah a great one!

Cabin in Afton

5 out of 5 average rating, 3 reviews

Quiet w/Hot Tub and 6 wineries within 10 mins.

MichaelRating, 5 stars1 week ago

This cabin was absolutely perfect for our honeymoon. Cozy, secluded, peaceful. It's also right on the Nelson 151, which is a road dotted with wineries and craft breweries. There was a new one to go to everyday! Back at the hooch, we enjoyed cooking, sitting on the porch, and relaxing in the hottub while listening to the nearby waterfall. Katie is a very responsive host and kept us informed with everything going on. We knew it was a couples' place right when we walked in. Cheers!

5 out of 5 average rating, 33 reviews

Home in Afton

The Vū, Afton w/ 360º Mountain Views

KristaRating, 5 stars1 month 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, 10 reviews

Cabin in Luray

"The Turtle" Romantic Luxury Cabin in Shenandoah

JenniferRating, 5 stars2 days ago

Morry has been an excellent host and responsive with any questions we had! The cabin's location is so convenient! About 10 minutes drive to the nearest major retail grocery store / fast food chains and 15 minute drive into Luray's city center for additional options on cafes and restaurants. Nearest Shenandoah Entrance will be Thornton Gap Entrance (24 minutes). With everything in a reasonable vicinity, makes planning so much easier and allowed us more time to spend on trails/relaxing. The cabin itself is gorgeous and well equipped with needed amenities! The hot tub was a big hit after coming back from hiking and a great way to end the day with a good soak. Appreciate Morry for allowing us to stay at this beautiful cabin and can't wait to be back!

5 out of 5 average rating, 19 reviews

Home in Nellysford

"Glass & Pine" Home close to Bold Rock &Vineyards

SaraRating, 5 stars2 weeks ago

Lovely place, very clean, stylishly decorated. It is roomy and has a fantastic view. Nice outdoor sitting areas. It is secluded. The only problem my family and I ran into was knowing what driveway to turn in. We failed to see a sign that displayed a house number at the end of the driveway. Other than that the house and our stay was outstanding.

Superhost

Cabin in Afton

4.85 out of 5 average rating, 39 reviews

Clonmel Cabin: Midterm Rental + Mountain View

IanRating, 5 stars9 months ago

If you’re looking for a beautiful place to enjoy the surroundings, I would highly recommend

Guest house in Waynesboro

4.92 out of 5 average rating, 74 reviews

Nona's Cottage-Waynesboro/Shenandoah Valley, VA

ChrisRating, 5 stars2 days ago

Cute little place in a quiet neighborhood. Much nicer place to stay than a hotel while visiting family in Waynesboro. We walked the mile into downtown to the restaurants and bars with no problem. Nice place for a weekend.