
Vacation rentals in Waynesboro
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Top-rated vacation rentals in Waynesboro
Guests agree: these stays are highly rated for location, cleanliness, and more.

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.

"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.

Luxe Yurt w/Hot Tub in the Heart of the Blue Ridge
Experience glamping, Blue Ridge style. Our luxury yurt is located at the top of a small hill, in the center of a 70 acre farmstead surrounded by natural beauty. Night Archer Farm is located off a quiet country road in Afton, Nelson County. It is private, but not remote. You are close to the Brew Ridge trail, wineries, breweries, skiing at Wintergreen, Blue Mountain Brewery, Devil's Backbone, golf, hiking, or driving the Blue Ridge Parkway. Hike directly from the Yurt up into the mountains!

Tiny Log Cabin
This tiny hand-hewn log cabin is a perfect, peaceful, and relaxing way to unwind and reconnect with your loved one or have a personal retreat for yourself. Nestled in the Blue Ridge Mountains on 300 acres of private land with plenty of room to explore and enjoy the wild life. Come witness the brilliant night sky lying in an open field with no city lights to diminish the experience. Minutes to Wintergreen Resort, the Appalachian Trail, Sherando Lake, 4 breweries, 6 wineries, and 3 cideries.

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!

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.

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.

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.

LaCasadeChiChi
A very comfy home for two in the heart of Nelson County. The views and location can’t be beat! This RV is located on the same property as “GreenHouseNelson” our other Airbnb here in Nelson County. Here you will find a lot of peace and nature. Tons of sunshine, mountain views, and brews!
Popular amenities for Waynesboro vacation rentals
Other great vacation rentals in Waynesboro

Serene Luxurious Cottage on the Brew Ridge Trail

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

The Garden Hideaway @ Bull Run

Shenandoah Valley Atelier: NEW Waynesboro Loft

Private Carriage House, close to Shenandoah & 151

Nona's Cottage-Waynesboro/Shenandoah Valley, VA

The Mountain View Nook

"Virginia Beauty" in Historic Tree Streets
When is the best time to visit Waynesboro?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$24,042 GYD | G$23,624 GYD | G$24,669 GYD | G$27,805 GYD | G$27,596 GYD | G$29,687 GYD | G$31,150 GYD | G$30,105 GYD | G$29,478 GYD | G$31,150 GYD | G$28,223 GYD | G$25,506 GYD |
| Avg. temp | 2°C | 4°C | 8°C | 14°C | 18°C | 22°C | 24°C | 23°C | 20°C | 14°C | 9°C | 4°C |
Frequently Asked Questions
How much does it cost to stay in boutique hotel rentals in Waynesboro?
Experience the best of Waynesboro with our boutique hotel rentals, starting at about $130 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there house rentals with a dedicated workspace in Waynesboro?
Yes! Work meets play with ease at over 10 house rentals in Waynesboro featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly apartment rentals in Waynesboro?
Four-legged friends are welcome in Waynesboro. Choose from more than 10 apartment rentals for guests traveling with pets.
Do bed and breakfast rentals in Waynesboro have a kitchen?
Absolutely! We offer over 10 bed and breakfast rentals with a kitchen in Waynesboro. Enjoy a tailored experience with all the comforts you desire.
Do boutique hotel rentals in Waynesboro have wifi?
Absolutely! We offer over 10 boutique hotel rentals with wifi in Waynesboro. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Waynesboro?
Waynesboro has more than 20 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do bed and breakfast rentals in Waynesboro have free parking?
Absolutely! We offer over 20 bed and breakfast rentals with free parking in Waynesboro. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Waynesboro?
Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with free parking, over 30 homes with a kitchen, over 30 homes with air conditioning, over 30 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Quick stats about vacation rentals in Waynesboro

Total vacation rentals
Explore 100 vacation rentals in Waynesboro

Nightly prices starting at
Waynesboro vacation rentals start at G$4,181 GYD per night before taxes and fees

Verified guest reviews
Over 4,550 verified reviews to help you choose

Family-friendly vacation rentals
30 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
100 of Waynesboro vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Waynesboro rentals

4.8 Average rating
Waynesboro stays are highly rated by guests—averaging 4.8 out of 5!
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- Luray Caverns
- Early Mountain Winery
- Boonsboro Country Club
- Amazement Square
- Ash Lawn-Highland
- Prince Michel Winery
- Chisholm Vineyards at Adventure Farm
- Massanutten Ski Resort
- Frontier Culture Museum
- Spring Creek Golf Club
- Car and Carriage Caravan Museum
- Wintergreen Resort
- The Plunge Snow Tubing Park
- Farmington Country Club
- Blenheim Vineyards
- Birdwood Golf Course
- Glass House Winery
- Cardinal Point Winery
- Meriwether Springs Vineyard and Brewery
- Burnley Vineyards