House holiday rentals in Waynesboro

4.99 out of 5 average rating, 137 reviews

A three-story wooden house is nestled among lush greenery in a forested setting. The deck and patio area are accessible, surrounded by trees and natural landscaping, creating a serene environment for relaxation.

Home in Nellysford

Cabin in Woods | Family & Dog Friendly | Fire Pit

Welcome to the Wooder House, a cozy haven nestled in the woods of Virginia's beautiful Nelson County! Enjoy relaxing and connecting in a private home centered on 38 wooded acres, but close to NelCo fun! - Peaceful nature retreat - Outdoor patio & fire pit - Great for families & dogs - Fully stocked kitchen - Private trail + hiking options nearby - 8+ min. to wineries, breweries, cideries, restaurants - 25 min. to Wintergreen Resort For more photos and fun, check us out on IG: @thewooderhouse

5 out of 5 average rating, 215 reviews

Home in Greenwood

Gorgeous Modern Mountain Home + Blue Ridge Views

GREENWOOD VISTA - Escape to our modern mountain retreat nestled along the Blue Ridge mountains. Whether you want to explore Shenandoah National Park, visit wineries, or relax in our hot tub with stunning mountain views, this gorgeous A-Frame home is the perfect place for you. We have thoughtfully appointed our home with everything you need to be comfortable. From a luxurious master suite, fully equipped kitchen, to coffee and wet bar, sauna, outdoor grill, billiard table, and a cozy fire pit.

4.99 out of 5 average rating, 172 reviews

A comfortable living area features leather sofas and a wooden coffee table, resting on a geometric-patterned area rug. Natural light filters through sheer curtains, illuminating the space. A ceiling fan and wall-mounted television are also present, adding to the room's functionality.

Home in Weyers Cave

Cozy Country Cottage

A cozy country cottage in the heart of the Shenandoah Valley with a million dollar view. To do? So much ,so close! Like antiques? Factory Antique Mall -8 miles Largest antique mall in America. Gotta golf? Lake View -11 miles Packsaddle- 18 miles To ski or not to ski! That's up to you. Massanutten Resort-20 miles. "Into" Caverns? Grand Caverns 5-miles. Oldest show cave in North America. Wine anyone? Cross Keys Vineyard and Bistro-7 miles Marceline Vineyards-5 miles. Or just chill out!

4.97 out of 5 average rating, 106 reviews

A charming one-story home is set against a blue sky with scattered clouds. The exterior features a combination of white bricks and a brown roof. A circular driveway is visible, with landscaped gardens and comfortable seating on the porch.

Home in Afton

The Branch at Afton Mountain Retreat

Welcome to The Branch at Afton Mountain Retreat in the heart of Brewery Trail/Route 151, Vineyard country and the foothills of the Blue Ridge Mountains. The Branch is located 1/8th 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.

4.94 out of 5 average rating, 321 reviews

Home in Mount Crawford

HOT TUB, WIFI, Near Buc-ee’s, I81, yet secluded!

Come relax in the hot tub and enjoy this peaceful getaway right on North River. We are tucked away in the countryside but just 5 minutes from I81 as well as 10 min to Bridgewater College, 15 min to Blue Ridge Community College, 17 min to JMU, and 25 minutes to Massanutten Resort. There are plenty of exciting adventures here in the heart of the Shenandoah Valley including, hiking, wineries, shopping, and lots of good food! We are just minutes from Buc-cee’s Rockingham location!!

4.89 out of 5 average rating, 167 reviews

The exterior of the building features a modern farmhouse design with white siding and stone accents at the base. Two large windows are framed symmetrically on either side of the front entrance, which is highlighted by tall, white columns. A neutral driveway leads to the entryway.

Home in Grottoes

New modern ranch house in adorable small town

Welcome to La Posada! The quaint town of Grottoes takes center stage in its close proximity to I81, neighboring the cities of Harrisonburg Waynesboro and Staunton and the towns of Elkton, Mount Crawford and Weyers Cave and with just a hop, you’re in Charlottesville via route 340 to I64. Grottoes residents take great pride in this close knit community. Grand Caverns is our Gem, a National Landmark known for being the oldest show cave! Please use 205 A sixth st when using GPS

4.97 out of 5 average rating, 215 reviews

A private hot tub is positioned on a spacious wooden deck, surrounded by lush greenery and trees. Two lounge chairs provide a comfortable seating area. The bright blue sky is dotted with fluffy white clouds, creating a serene outdoor environment with expansive mountain views in the background.

Home in Franklin

Pine Ridge Manor • A+ Privacy • Pool • BBQ • Games

Mountain Views ✔ Wildlife ✔ Stargazing ✔ Hot Tub ✔ ★ "The pictures don’t do this wonderful place enough justice!" ✣ Game room w/ pool table ✣ Backyard w/ fire pit + wood ✣ Deck w/ hot tub + sun loungers ✣ Fully equipped + stocked kitchen ✣ Parking → garage (2) + driveway (2 cars) ✣ Gas BBQ grill + outdoor dining ✣ Workspace + 260 Mbps wifi ✣ Onsite washer + dryer 16 mins → Sweetwater Farm Trail Center 20 mins → DT Franklin (cafes, dining, shopping)

Superhost

A cozy living area is highlighted by a wood-burning stove with a green brick surround. An inviting sectional sofa is positioned around a coffee table, while a mounted television above the fireplace allows for entertainment. Natural light filters through multiple windows adorned with white shutters.

4.77 out of 5 average rating, 151 reviews

Hot Tub - Fire Pit - Game Room

Howdy! Nestled perfectly between the North Terminus of the Blue Ridge Parkway, the entrance to Skyline Drive, all of the Afton wineries, the Beerwerks Trail, Wintergreen Resort, and Downtown Waynesboro, this four bedroom house with a fully stocked game room, two patios, a fire pit, and hot tub is the perfect spot to relax after a long day of enjoying the Shenandoah Valley.

4.99 out of 5 average rating, 248 reviews

A brick home features a welcoming front porch adorned with potted plants and comfortable seating. Lush greenery surrounds the property, and a gravel driveway leads to the entrance, enhancing the inviting feel of the rural setting.

Home in Dayton

Country Oasis. No Cleaning Fees. Xfinity Internet.

Country Oasis, located between the Allegheny and Blue Ridge mountains, is a lovely get away for anyone wanting the privacy of an entire home to yourself. It is just a short drive from JMU, EMU, and Bridgewater College. Harrisonburg, "the friendly city" is just a 15 minute drive from our location. There are two Farmers Markets and numerous other attractions nearby.

The cabin exterior features a welcoming porch with steps leading to a landscaped yard. Soft evening light casts a warm glow from the windows, highlighting the charming architecture against a backdrop of colorful twilight sky. The expansive green lawn extends towards the horizon.

4.94 out of 5 average rating, 175 reviews

Ridgeview Retreat: Mountain Views and Pet Friendly

Ridgeview Retreat is a cozy cabin situated beautifully on over 15 sprawling acres with gorgeous mountain views. Enjoy the peace and quiet of the country, but also proximity to Downtown Staunton and easy access to Harrisonburg. This 3 bedroom cabin sleeps 7 and boasts gorgeous outdoor spaces with a firepit, swings, and land to roam.

4.89 out of 5 average rating, 398 reviews

A winding gravel driveway leads to a spacious home, surrounded by a lush green lawn. A large tree provides shade next to the house, which features a covered front porch. The setting includes open fields and a sky filled with soft clouds.

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

Early autumn foliage displays a rich tapestry of reds and greens, with distant mountains serving as a backdrop under a clear blue sky. The vibrant leaves gently frame the scene, emphasizing the natural beauty of the area.

4.85 out of 5 average rating, 171 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.

Popular amenities for house rentals in Waynesboro

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A spacious living area features a stone fireplace as the focal point, framed by large windows that offer views of the surrounding trees. A comfortable sectional sofa is arranged around a coffee table, with a television positioned on a media console to the side.

4.96 out of 5 average rating, 106 reviews

Cozy 5-bedroom home for large gatherings.

4.93 out of 5 average rating, 232 reviews

The exterior of Pine Lake Lodge is displayed, featuring a stone chimney and a covered porch with several chairs. Lush green grass surrounds the lodge, complemented by trees and colorful foliage in the background, creating a serene outdoor setting.

Home in Charlottesville

Pine Lake Lodge

The exterior of a multi-level home is nestled among trees, with warm lighting illuminating the porch and deck. The spacious deck features a staircase leading down, surrounded by autumn leaves, creating a welcoming atmosphere.

4.89 out of 5 average rating, 141 reviews

Lily Pad - 5 Br/4 Ba Wintergreen Family Retreat

5 out of 5 average rating, 105 reviews

Home in Massanutten

Guests Rave: Clean & Spacious Mountain Getaway

4.98 out of 5 average rating, 157 reviews

The entrance to Fairhill Farm is marked by a white wooden sign displaying the name, set against a backdrop of rolling hills adorned with autumn foliage. A vibrant red bush frames the sign, contributing to the natural beauty of the landscape.

Home in Stanardsville

Charming Carrie's Cottage at Fairhill Farm

4.98 out of 5 average rating, 103 reviews

The exterior of Sunset Retreat features a welcoming entrance with a decorative sign and a covered porch. Lush shrubs frame the doorway, and a stone pathway leads to the steps. A warm, neutral color palette complements the nature surrounding the home.

Home in Aroda

Sunset Retreat a cabin off the beaten path

A modern living area features a sleek leather sectional sofa adorned with patterned cushions, accompanied by a wooden coffee table. Large windows offer views of the surrounding trees, while natural light enhances the inviting space. A floor lamp adds illumination next to the sofa.

4.96 out of 5 average rating, 112 reviews

Peaceful 3-BR Mountain home w/Fireplace + Hot tub

A spacious bedroom features a high, wood-beamed ceiling and a large window providing natural light. The bed is dressed in navy bedding with a plaid blanket draped across it. A wooden dresser and lamp complement the rustic decor, and a mounted TV is positioned above.

4.98 out of 5 average rating, 206 reviews

Hottub Ski In/Ski Out Renovated Chalet Lower Tyro

Weekly house rentals

An open living area showcases a spacious sectional sofa facing a round coffee table. Wooden beams are visible on the ceiling, while large sliding glass doors lead to the backyard. A dining table for several is positioned nearby, creating a seamless flow between spaces.

5 out of 5 average rating, 30 reviews

New Reno! Central to Skyline, Staunton, Cville

A cozy living area features a light-colored sofa facing a fireplace, creating a focal point. To the side, a comfortable armchair is paired with a small side table. A television is positioned across the room, with natural light illuminating the space from large, partly draped windows.

4.98 out of 5 average rating, 56 reviews

The Red Hen Historic Cottage

5 out of 5 average rating, 44 reviews

A modern guesthouse showcases a sloped roof and wooden accents, surrounded by lush green grass. Expansive glass doors offer views of the interior, while a well-defined stone pathway leads to the entrance. The property is set against a backdrop of rolling hills and trees.

Home in Crozet

Orso Blu one-of-a-kind VIEWS in Crozet

A welcoming living area features two leather couches arranged around a wooden coffee table, which is complemented by a patterned rug. Large windows allow natural light to illuminate the space, offering views of the surrounding trees. Sliding glass doors provide access to an outdoor deck.

4.99 out of 5 average rating, 140 reviews

Close to skiing! | King Beds | Fireplace | Hot Tub

A spacious kitchen is featured, showcasing light-colored cabinetry and a large island with seating for four. Modern appliances, including a refrigerator and stove, are integrated with ample counter space. Natural light flows through large windows, enhancing the inviting atmosphere.

4.99 out of 5 average rating, 69 reviews

Willow Grove Wineries, Breweries, Hiking,Hot Tub

A cozy living area is furnished with two black sofas and a coffee table centered on a patterned rug. A flat-screen TV is mounted on the wall, with a decorative piece on the table. Natural light enters through two adjoining windows adorned with blinds.

4.98 out of 5 average rating, 47 reviews

Cute Place in Waynesboro

4.94 out of 5 average rating, 98 reviews

A spacious living area features a comfortable sectional sofa adorned with various patterned cushions. Two tables with lamps flank the seating, providing warm lighting. A decorative wall accent and window treatments enhance the inviting aesthetic, with natural light illuminating the hardwood-style flooring.

Home in Afton

Centrally located on the brew trail

An aerial view of a downtown neighborhood is displayed, showcasing a mix of historic homes and trees. The landscape features rolling hills in the distance, with a blend of residential streets and parked vehicles visible.

5 out of 5 average rating, 224 reviews

* Award-Winning Renovation * Ideal Location *

Private house rentals

4.99 out of 5 average rating, 71 reviews

The historic Gray House features white brick walls and a classic southern-style porch. Flanking the entrance are potted plants, and tall windows allow natural light to fill the space. A large tree adds to the charm of the surrounding landscaped yard.

Home in Harrisonburg

Historic Inglewood - peaceful farm stay near JMU

5 out of 5 average rating, 44 reviews

A spacious screened-in porch features comfortable seating arrangements with plush cushions and a round table. Expansive windows offer unobstructed views of lush green meadows and distant mountains under a bright blue sky, enhancing the connection to the surrounding nature.

Home in Afton

The Vū, Afton w/ 360º Mountain Views

A dining area is showcased with a stylish table set for six. Dark blue cabinets contrast with a floral wallpaper design. A circular mirror hangs on the wall, reflecting natural light. A colorful area rug adds warmth to the wooden floor beneath.

4.96 out of 5 average rating, 48 reviews

•Staunton | Boho Bungalow•

A spacious house is set amidst a serene winter landscape, surrounded by trees and blanketed in snow. The wooden deck extends around the house, offering ample outdoor space. Large windows allow for natural light, enhancing the connection with the surrounding nature.

4.93 out of 5 average rating, 68 reviews

4 min to Ski: Whispering Creek Hot Tub King Beds

5 out of 5 average rating, 14 reviews

Peabody Long / short term rental

A cozy bedroom features a spacious white bed adorned with a textured quilt and decorative pillows in soothing green and blue hues. Two bedside tables with lamps flank the bed, providing soft lighting, while elegant vases add a touch of style to the space.

5 out of 5 average rating, 94 reviews

Enchanting, historic home - short walk to downtown

The exterior of the home is framed by tall, bare trees, showcasing a modern gray structure. A prominent stone chimney rises above the gabled roof. Wooden decks and steps lead up to the entrance and wrap around the structure, offering access to scenic views.

4.93 out of 5 average rating, 40 reviews

Walk to Ski! Magnificent Mntn View Stone Fireplace