Holiday houses in Waynesboro

Idyllic Cottage Retreat

⭐️ Condé Nast Traveler Approved ⭐️ Cozy cottage nestled on a historic 400-acre Blue Ridge Mountain farm abutting Shenandoah National Park. Every space inside this cozy cottage is creatively styled, with tons of perfectly imperfect charm. Outside, a hammock beneath the elm trees, fire pit and grill, all allow for enjoying the splendor of this peaceful enclave. Excellent day-tripping to many of central Virginia's celebrated wineries and breweries, as well as scenic drives and hiking trails.

Spacious lower level Airbnb! READ SUMMARY!

Hello everyone! I’m not going to try to convince you to stay at this Airbnb but instead address the issues that guests have complained about in reviews. This listing is priced accurately and cheap because there isn’t much besides 2 king beds, bathroom, washer/dryer. There is a bit of noise from upstairs when people walk around but usually no later than 11 PM. Please keep in mind when reviewing that you’re not paying very much to stay here. If you’re going to complain, please stay elsewhere.

The LoriAnn, A Boutique Stay New Sleep Number Bed

This beautifully restored 1940’s home in the City of Waynesboro is just a short drive from the Blue Ridge Parkway. Modern amenities, light complimentary breakfast items and assurance of comfort awaits! Enjoy one of a kind Autographed Movie and TV Memorabilia. The spacious front porch is yours to enjoy 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.

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 downtown Historic Waynesboro and the riverside park, its restaurants and stores can entertain even the peculiar palate or collector, some are right across the street! Fully fenced in back yard, so bring the pups to play!

Best Spot on the Wine/Brew Trail!

Charming, private, efficiency apartment located in the center of winery/brewery country! This efficiency offers fiber internet (super fast)! Less than a minute to Blue Mountain Brewery, Flying Fox Vineyard, and Valley Road Vineyard. Less than 5 minutes to Veritas Vineyard, Cardinal Point Vineyard, Silver Back Distillery, Afton Mountain Vineyards. 5-10 minutes to Bold Rock Cidery, Devils Backbone Brewery, Brewing Tree Brewery, Mountain Meadery, Hill Top Berry Farm, and so many more.

The Laurel Hill Treehouse

Tucked away in the woods, this Scandinavian-inspired treehouse is a quiet, peaceful spot designed for a relaxed couples getaway. Surrounded by trees and overlooking beautiful woodland views, it’s an easy place to slow down and unwind. Spend your time on the wraparound porch, soak in the hot tub, cool off in the creek, or settle in by the fire at night. This is a serene, comfortable retreat where you can reset, enjoy all that nature has to offer, and simply be present.

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.

Walker's dream. Close to downtown.

Centrally located near the library, Gypsy Hill Park, and downtown Staunton, our private, walkout basement apartment has individually controlled heating and air conditioning. It includes a brick patio, private rear entrance and historic details from the late 1800's. It is generally quiet, but you may sometimes hear the two adults upstairs. Come enjoy this peaceful and centrally-located space.

2 King/1 Twin Near Downtown & UVA

⭐️Two bedroom lower-level apartment (2 king beds, 1 twin XL, 1 toddler bed, 1 pack-n-play) in a quiet neighborhood near downtown! ⭐️Our guests rave about the excellent value, amenities, & cleanliness! 📍1 mile from UVA Hospital and Downtown Mall 📍1.6 miles from UVA ⭐️No smoking! ⭐️Please read note about the slope to the entrance 🟢The person booking must be present during the stay

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.

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.

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, 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.