House holiday rentals in Waynesboro

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, 144 reviews

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

Welcome to Blackrock Escape! Dog friendly, 2BR/2.5BA mountain home in prime location at Wintergreen Resort. 3-min drive to the Mountain Inn. Walk to hiking trails–the Plunge Trail/Blackrock Park is only a 2-min walk. Two BRs on first floor - both with King-size Helix mattresses, smart TVs, and en suite bathrooms. Wood burning fireplace, games, puzzles, 65” smart TV in living room. Two decks w/gas grill and hot tub. Keurig K-Duo coffee maker and dishwasher in kitchen. Full-sized washer and dryer.

4.99 out of 5 average rating, 144 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, 217 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 bedroom suite, fully equipped kitchen, to coffee and wet bar, sauna, outdoor grill, billiard table, and a cozy fire pit.

4.97 out of 5 average rating, 101 reviews

Home in Roseland

Stargazing on 12 Acres: Hot Tub 55"TV Fire Pit

Relax with the family on 12 private acres at our peaceful, brand new construction farmhouse. We're just 12 miles to Wintergreen Ski Resort and Stoney Creek Golf, breweries, and wineries. Sleeps 8: K, K, Q + daybed w/ trundle. ★Amazing mountain views ★Hot tub for 6 people ★Outdoor shower ★Rockers, Adirondacks chairs for idle stargazing ★Gas grill ★Teak dining table seats 6 ★Indoor/outdoor gas fireplaces ★View 55” TV from comfy leather sofa/kitchen ★Pack 'n Play/Bassinet/High chair ★Mud room

4.99 out of 5 average rating, 281 reviews

A charming cottage is positioned alongside a gently flowing trout stream, with a backdrop of lush greenery. Rocks line the water's edge, and a large, fenced yard surrounds the home, providing a peaceful setting. A red roof contrasts beautifully with the natural surroundings.

Home in Tyro

Bear Creek Inn 3 BR House Creekside

3BR HOUSE, QUIET CREEKSIDE RETREAT, PET FRIENDLY, FENCED YARD ENTIRE 3 BR mountain home with a large fenced backyard and a babbling creek—perfect for couples, families, and pets. Minutes to Crabtree Falls, the Appalachian Trail head, and George Washington National Forest. Unwind in nature, then explore Nelson 151 breweries and wineries or head to Wintergreen Resort just 12 miles away. Space, privacy, and adventure all in one unforgettable stay. Pet fee auto added when indicated at booking.

4.99 out of 5 average rating, 175 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!

4.94 out of 5 average rating, 331 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!!

4.9 out of 5 average rating, 104 reviews

A two-story house is set amidst vibrant autumn foliage, showcasing a covered porch that invites relaxation. A garage is visible on the left, with a gravel driveway leading to the entrance. Sunlight filters through trees, illuminating the exterior of the home.

Home in Crozet

Beauchamp House 2 BD Fishing Hiking Lake

The Beauchamp House is in the Blue Ridge Mountains of Virginia, near the Shenandoah National Park and Charlottesville, Va. Ideal for couples, friends and families. One pet welcome with additional $100 fee. Enjoy 129 acres with hiking trails, small lake, free mountain bikes, canoes, fishing. Wineries and fine dining nearby. Includes high speed internet and Roku TV. House has a separate basement apartment with a separate entrance and driveway.

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.

4.78 out of 5 average rating, 154 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.

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.

4.94 out of 5 average rating, 100 reviews

Centrally located home on the brew trail

Escape to our modern farmhouse in the Blue Ridge Mountains! This recently renovated 2-bed, 1-bath home comfortably fits 4. Enjoy serene mountain views from a quiet, family-friendly setting, just minutes from the famous brew trail's wineries and breweries. Features a firepit, fast Wi-Fi, and a fully equipped kitchen. Your perfect mountain retreat awaits!

4.89 out of 5 average rating, 404 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.

4.97 out of 5 average rating, 289 reviews

A warm kitchen area features wooden cabinets, white countertops, and a variety of appliances. The dining table, surrounded by wooden chairs, is positioned nearby. Natural light filters through a window, illuminating the space, while a red accent wall adds color.

Home in Harrisonburg

The Washhouse

We are conveniently located along Rt 33 about 10 minutes from EMU, JMU. The George Washington National Forest, Shenandoah National Park, Skyline Drive, and numerous caverns provide endless opportunity for outdoor adventures. There is also abundant shopping and dining nearby in Harrisonburg, Dayton, or Bridgewater.

Popular amenities for Waynesboro house rentals

Kitchen

Wi-Fi

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, 108 reviews

Cozy 5-bedroom home for large gatherings.

4.93 out of 5 average rating, 233 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

4.98 out of 5 average rating, 123 reviews

The image displays a hot tub surrounded by lush greenery at dusk. String lights illuminate the area, creating a soft glow. Adirondack chairs are arranged on a wooden deck, providing a comfortable space for relaxation near the hot tub.

Home in McGaheysville

Luxury Retreat~Hot Tub~Sauna~Game Rm~2 King Suites

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, 145 reviews

Lily Pad - 5 Br/4 Ba Wintergreen Family Retreat

4.96 out of 5 average rating, 228 reviews

A private in-ground swimming pool is surrounded by a wooden deck and sun loungers. Shade is provided by a canopy, and lush greenery is visible in the background, highlighting the calming outdoor setting. The pool features a net for recreational activities.

Home in Lovingston

Seasonal Private Pool - All Year Hot Tub

5 out of 5 average rating, 108 reviews

Home in Massanutten

Top 1% ~ Fireside Ski Retreat w/ 2 King Suites

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

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, 113 reviews

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

Weekly house rentals

4.96 out of 5 average rating, 208 reviews

A spacious living area displays soft beige sofas paired with dark blue accent tables. Natural light filters through large windows, enhancing the warm, neutral tones of the walls. A glimpse of the kitchen and bedroom can be seen through open doorways, providing a sense of flow.

Home in Charlottesville

Woodwind Cottage

A Cape Cod-style home is set on a spacious green lawn, framed by trees showing autumn colors. The wrap-around porch is visible, with steps leading to the entrance. Soft morning light illuminates the house, highlighting its architectural details.

4.98 out of 5 average rating, 170 reviews

The Inn at Blue Mountain Brewery

The exterior of a modern farmhouse is showcased, featuring large windows that reflect the surrounding trees. A spacious patio is seen, with a set of outdoor chairs. The house's white siding contrasts with the green landscape and blue sky, creating an inviting atmosphere.

4.95 out of 5 average rating, 114 reviews

Hilltop at Mountain View Meadow

5 out of 5 average rating, 52 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 comfortable gray sectional sofa is positioned near large windows, allowing natural light to brighten the space. Decorative throw pillows, including one with stripes, add subtle texture. A wooden side table holds a lamp, while a patterned area rug contributes warmth to the room.

4.96 out of 5 average rating, 136 reviews

Min to Wineries | Breweries | Restaurants | Trails

A living room is presented with a large, brown leather sofa in the foreground. An angular coffee table occupies the center, surrounded by two patterned armchairs. A television is positioned on a dark wood media console against a wall, with a potted plant adding a touch of greenery near a window dressed with light curtains.

4.95 out of 5 average rating, 263 reviews

CritzerHouse - on 151- Walk to the Brewery!

4.94 out of 5 average rating, 431 reviews

A country bungalow is presented in a fenced yard, surrounded by grassy fields. The exterior features a simple design with a front porch, two accessible entrances, and robust landscaping. Nearby trees provide shade, while a clear sky enhances the peaceful rural setting.

Home in Harrisonburg

The Homeplace - Private House with Backyard

A historic two-story brick house is framed by vibrant autumn leaves, showcasing a well-maintained lawn and hedges. Two porches extend from the structure, providing outdoor seating areas. The surrounding trees create a natural barrier, enhancing the home's serene setting in a tranquil neighborhood.

5 out of 5 average rating, 42 reviews

"Virginia Beauty" in Historic Tree Streets

Private 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, 31 reviews

New Reno! Central to Skyline, Staunton, Cville

4.98 out of 5 average rating, 64 reviews

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.

Home in Staunton

The Red Hen Historic Cottage

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, 73 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, 48 reviews

Cute Place in Waynesboro

4.96 out of 5 average rating, 53 reviews

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.

Home in Staunton

•Staunton | Boho Bungalow•

4.92 out of 5 average rating, 24 reviews

Home in Staunton

Peabody short term rental

4.96 out of 5 average rating, 28 reviews

The exterior of the guesthouse features charming wooden siding painted in a deep red hue. A welcoming porch with two chairs is adorned with hanging greenery. The sloped roof and surrounding landscaping contribute to the overall inviting appearance of the property.

Home in Dayton

Dayton Guesthouse