House vacation 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, 142 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, 141 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

Superhost

A outdoor fire pit area is surrounded by several comfortable chairs, set within a pebbled landscape. Soft blankets are draped over the back of one chair. In the background, a sparkling pool is visible, framed by lush greenery and trees.

4.81 out of 5 average rating, 183 reviews

Downtown Riverview Castle with Pool and Hot Tub!

Enjoy the perfect combination of city (short walk to downtown shops, restaurants, parks, South River Greenway) & peaceful scenery. Spend all day in the pool (Mar - Sept) & night in the hot tub; all while overlooking the famous South River Rapids. Originally built in 1939. Historic charm while boasting luxurious additions & modern amenities! Eclectic, happy & charming. 6 + BR and over 3300 square ft for the whole family to enjoy. 12+ person dining table, 4 island chairs, & 8+ outdoor dining.

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 master suite, fully equipped kitchen, to coffee and wet bar, sauna, outdoor grill, billiard table, and a cozy fire pit.

A vast expanse of green grass stretches across the foreground, framed by lush orchard trees. Rolling hills covered with foliage rise in the background, under a clear blue sky dotted with soft white clouds, creating a serene rural atmosphere.

4.97 out of 5 average rating, 103 reviews

Perfect getaway among the orchards of Batesville

Unwind at this very special oasis, highly rated by our guests! Stillhouse Creek Cottage has everything you need: large kitchen, dining nook, living room with queen sofa bed, and two bedrooms with queen and king beds. The outdoor deck is perfect for sitting and dining under the sun and the stars, with a view for miles. Relax at night in the hot tub! When you’re ready to explore, hike on nearby Appalachian Trail, swim the local reservoirs, and visit many close-by wineries, breweries and music!

4.99 out of 5 average rating, 174 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!

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.

4.97 out of 5 average rating, 109 reviews

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, 325 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!!

A contemporary mountain home is surrounded by snow-covered grounds, with a softly lit entryway visible through the glass doors. Frosted trees frame the exterior, highlighting the inviting warmth inside, contrasting with the winter landscape.

4.96 out of 5 average rating, 114 reviews

Cliffs Edge- A Contemporary Mountain Home

An open floor plan with high ceilings and large skylights, this amazingly engineered home will stun you with its incredible mountain views! This spacious home, with its cantilevered decks, makes this perfect for any family. The large upstairs loft, adjacent to the upstairs bedrooms, offers movies, games, puzzles, and comfortable seating. Wi-Fi, Netflix, and Samsung Smart hub give plenty of entertainment options. The spacious living area and dining room have abundant seating for all.

4.99 out of 5 average rating, 279 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, small 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.

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, 152 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.

4.89 out of 5 average rating, 400 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.

Popular amenities for Waynesboro house rentals

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, 107 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, 142 reviews

Lily Pad - 5 Br/4 Ba Wintergreen Family Retreat

4.96 out of 5 average rating, 225 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

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 wooden walkway leads to the entrance of the house, framed by vibrant pink rhododendron flowers. Tall trees provide a natural backdrop, with dappled sunlight filtering through the leaves, creating a serene outdoor setting.

4.95 out of 5 average rating, 135 reviews

Bear's Mountain Escape

4.89 out of 5 average rating, 112 reviews

An indoor saltwater pool area features a large, tranquil pool surrounded by multiple windows allowing natural light. Lounge chairs line one side, with red and white striped towels neatly arranged. The ceiling is accented with skylights, enhancing the spacious feel.

Home in Luray

Indoor Heated Pool~WiFi~ Arcade~Fire Pit~Views

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, 207 reviews

Hottub Ski InOut Renovated Chalet Lower Tyro Slope

Weekly house rentals

4.99 out of 5 average rating, 342 reviews

A charming single-story house is displayed against a backdrop of lush greenery. A gentle slope leads to the front porch, which features a railing. Sunlight filters through the trees, casting a warm glow on the exterior, while a gas grill is positioned on the patio.

Home in Dayton

Home on Mole Hill - A Quiet Getaway

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

4.95 out of 5 average rating, 129 reviews

Aerial view of a picturesque home surrounded by vibrant autumn foliage. Rolling hills are visible in the background, while the golden and orange leaves create a warm tapestry across the landscape, complemented by a tranquil sunset sky.

Home in Rileyville

ShenandoahEscape~HotTub~OutdoorCinema~DogFriendly

4.94 out of 5 average rating, 176 reviews

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.

Home in Staunton

Ridgeview Retreat: Mountain Views and Pet Friendly

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, 262 reviews

CritzerHouse - on 151- Walk to the Brewery!

4.96 out of 5 average rating, 170 reviews

An expansive living area features large floor-to-ceiling windows showcasing a vibrant sunset. A festive tree adorned with lights stands beside the windows, while serene views of a pond and outdoor seating are visible through the glass. Soft furnishings enhance comfort in the space.

Home in Nellysford

Glass House | Mountain & Water Views @ Wintergreen

4.95 out of 5 average rating, 419 reviews

A charming Craftsman-style cottage is presented, featuring a welcoming front porch with rocking chairs. A lush green lawn surrounds the home, complemented by mature trees. The exterior showcases a soft grey color, and the entrance is marked by a wooden door with house number 536.

Home in Woolen Mills

High Note | Parking X3 | Sleeps 6 | Rivanna Access

A spacious, two-story structure with a modern design is surrounded by greenery. The exterior features large, multiple-pane windows framed in red, with a balcony that offers outdoor access. An artistic metal sculpture is positioned in the foreground on a well-manicured lawn.

4.96 out of 5 average rating, 366 reviews

Spacious Afton Estate: Brew Ridge Trail w. Firepit

Private house rentals

The historic home showcases a classic colonial facade with white columns and large windows. A brick pathway leads through landscaped gardens featuring flowering shrubs, while an American flag is displayed at the entrance. Lush green grass surrounds the inviting entry.

5 out of 5 average rating, 21 reviews

Large historic home on 7+ acres.

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

5 out of 5 average rating, 48 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

4.98 out of 5 average rating, 61 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, 70 reviews

Willow Grove Wineries, Breweries, Hiking,Hot Tub

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.

5 out of 5 average rating, 45 reviews

The Vū, Afton w/ 360º Mountain Views

4.96 out of 5 average rating, 54 reviews

A contemporary home is showcased against a wooded backdrop, featuring large windows that enhance natural light. A spacious deck is fitted with seating and a dining table, inviting outdoor relaxation. Decorative string lights add a subtle charm, highlighting the entrance area.

Home in Nellysford

Glass & Pine, close to Bold Rock & Vineyards

A spacious deck features two lounge chairs and two wooden rocking chairs, offering a setting for relaxation. The surrounding area showcases lush green mountains under a clear blue sky, with expansive views of the valley below.