Holiday rentals in Waynesboro

Cozy Mountain Cabin

Snuggled in the Blue Ridge. Secluded from the crowds. Experience your visit in an authentic log cabin. Spacious sleeping loft. Perfect romantic escape, friends getaway, or personal retreat. Workout area/sitting room. Fresh eggs (in season), wine, tea, coffee. 1G Internet, SMART TV. A/C. Less than 2 miles to Devil's Backbone and Bold Rock. Minutes from App. Trail, Wintergreen Resort, breweries, wineries, cideries, restaurants, horseback riding, hiking trails, outdoor concerts, & antique shopping.

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.

"Country Star"- Suite at Cross Keys

Welcome to our private, cozy suite, Country Star. A sunny walkout basement apartment with patio and easy parking next to entrance makes coming and going a breeze. Country Star features a kitchenette, with table and chairs, one bedroom with queen bed and closet, and a full bath/shower. It provides comfortable space for two, with extra space for a pack-n-play or fold out lounge chair/bed for a third person. (See note in 'other'). Our space offers convenience and comfort, with self check-in.

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!

1 bedroom condo, walk to the slopes !

Cozy 1BR Wintergreen condo ⛷️❄️ 5-minute walk to the ski slopes, resort village, and mountain-too market, with snow tubing only minutes away. Enjoy a fully stocked kitchen, premium coffee and teas, cooking oils and spices. Relax by the wood burning fire and enjoy a smart TV, fast WiFi and games. Comfortable queen bed in the bedroom plus new queen sleeper sofa in the living room. Private furnished patio with peaceful wooded views and close access to the village for après-ski.

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

Little Cottage

Located in the Beautiful and historical Shenandoah Valley. If you enjoy outdoor activities, the Valley is the place to be. This 450 sq ft Studio is minutes from Jame Madison University, Bridgewater College, and Mary Baldwin University. Less than 2 miles from Blue Ridge Community College. 5 mins from Shenandoah Valley Regional Airport. Massanutten Resort is a short drive from this location. Located less than 1 mile from Interstate 81 exit 235.

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.

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.

Moorman’s River Retreat

Beautiful setting, located within 5 minute drive to 3 wineries in White Hall, within 10 minutes to additional 3 wineries and 2 breweries. Hiking trails and nearby public access to the designated scenic Moorman's river for fishing, swimming or enjoying a picnic. Fishing and boating in lake just steps in front of cottage. Outdoor mini- grill available for cooking.