Holiday rentals in Waynesboro

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

Cottage in Afton

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.

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, 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.

4.9 out of 5 average rating, 284 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!

4.95 out of 5 average rating, 366 reviews

Flat in Staunton

Travelers Nook - close to downtown

The TRAVELERS NOOK is a cute, cozy, one bedroom apartment close to downtown Staunton! It’s located on the second floor, with a private entrance. It has all the charm that you would expect to find in a cute studio apartment! Built by a local architect Tj Collins in the 1920’s. This quaint space has everything you need to enjoy your stay here in Staunton! We do accept small pets on approval with a pet cleaning charge.

4.91 out of 5 average rating, 286 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.

4.93 out of 5 average rating, 650 reviews

Guest house in Staunton

The Firefly Springhouse

Private cabin, with bath, located in a quiet country setting, close to town and easy access to two Interstate highways. Comfy queen bed, 400 ct sheets. Climate control with state of the art Trane system. Mini-fridge, microwave, and Keurig coffee maker are included. High speed wireless internet and basic cable TV. All varieties of people are welcome here.

Guest house in Waynesboro

4.92 out of 5 average rating, 403 reviews

The Stable

Our guesthouse is located in the historic Tree Streets Neighborhood of Waynesboro, VA, an official Appalachian Trail town, located at the southern end of the Shenandoah National Park. We've aptly named the guesthouse "The Stable" because it was originally built and functioned as a stable. It has since been converted into a cozy cottage for guests.

4.96 out of 5 average rating, 217 reviews

Farm stay in Waynesboro

Farmhouse at the foot of the Blue Ridge Mountains

Updated, pet-friendly farmhouse with extra-large fenced in yard, located in Waynesboro. Located on a 60 acre farm surrounded by nearly a mile of river - 10 minutes from Skyline Drive & Blue Ridge Parkway - 15 minutes to Rt. 151, with unlimited wineries and breweries - 30 minutes to Charlottesville, UVa -30 minutes from Wintergreen

4.88 out of 5 average rating, 355 reviews

Home in Stuarts Draft

Blackwood Air B & B

Enjoy this spacious dwelling while viewing the Blue Ridge Mountains, Watch the freight train make its way around the curve or listen to the sheep as they graze in the pasture. Nearby outdoor activities are various hiking trails, Skyline Drive Parkway, or a local Shenandoah Acres lake. Only 10 miles from Wintergreen Resort.

Superhost

4.85 out of 5 average rating, 156 reviews

Prickly Pear Cottage *5 minutes from skyline dr.*

Prickly Pear Cottage is located right at the base of Afton mountain in Waynesboro. You’re just minutes from hiking, breweries and vineyards! This home was designed with the traveler in mind. You will love the spacious great room, large rec room in the basement outdoor space for your furry friends and the kids.

Holiday rentals for every style

Get the amount of space that is right for you

Houses

A space that's all yours, with room for everyone

Cabins

Kick off your hiking boots at these rustic lodgings

Hotels

Stylish accommodation and amenities

Popular amenities for Waynesboro holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Waynesboro

5 out of 5 average rating, 15 reviews

New Reno! Central to Skyline, Staunton, Cville

MckenzieRating, 5 stars1 month ago

Absolutely loved the house. So much so, going to build a future house based on this home! Will be staying here every time we come back go to the Charlottesville/Waynesboro area. House is immaculate! Reagan is a great host, and very responsive!

Treehouse in Stanardsville

5 out of 5 average rating, 45 reviews

CloudPointe Retreat

KatherineRating, 5 stars3 days ago

This place was even more breathtaking in person! The views were absolutely stunning, and the treehouse was spotless, beautifully designed, and thoughtfully decorated with every little detail in mind. It’s clear a lot of care went into creating such a unique and relaxing space.

4.98 out of 5 average rating, 82 reviews

Yurt in Afton

Mountain View Getaway Yurt

HaileyRating, 5 stars3 weeks ago

Our time staying at the yurt was above and beyond what we expected. The property and the yurt itself are so serene and enjoyable. Michelle is the most friendly host I have encountered, and talking with her about her goats brought so much joy! It is clear from the layout of the yurt to the care of the property all the way through the way they care for each and every guest and Michelle and her family truly love hosting. And that is something worth far more than five stars!

4.89 out of 5 average rating, 83 reviews

Gameroom~Gym~Fire Pit~Walk to River & Downtown!

Rajvardhan AjitRating, 5 stars1 month ago

Very helpful. House was really good and clean. Would definitely recommend

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 stars2 days 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!

4.97 out of 5 average rating, 38 reviews

Cute Place in Waynesboro

AmyRating, 5 stars2 weeks ago

We had a great stay here! Everything was super clean and great location. Clarence was very responsive and helpful with local recommendations!

5 out of 5 average rating, 27 reviews

Guest house in Greenwood

Private Carriage House, close to Shenandoah & 151

AryannaRating, 5 stars1 week ago

Matt’s place was great for me and my husband to spend our wedding night! We got married in charlottesville and wanted a small stay-cation before leaving for our honeymoon and this was the perfect spot to rest after our wedding. The airbnb is adorable and we easily went into Crozet during the day. Upon arrival, we weren’t sure we were in the right spot because there was a “posted: private property sign” on the driveway but I contacted Matt and he replied very quickly saying it was just leftover from previous owners. All was perfect after that! The kitchen doesn’t have a stove but they provided a one burner hot- pad that worked very nicely! I was slightly worried about that, but it turned out great.