Vacation rentals with outdoor seating in Waynesboro

5 out of 5 average rating, 246 reviews

A cozy cottage, named the 'Sugah Shack,' is nestled amidst the rolling hills of the Blue Ridge Mountains. The white exterior contrasts with the vibrant greenery surrounding the property, while the majestic mountains form a picturesque backdrop against a bright, partly cloudy sky.

Cottage in Afton

Cozy Mountain Cottage on Brew/Wine Trail-King Bed

Welcome to the Sugah Shack, a cozy, beautifully appointed new construction cottage nestled in the foothills of the Blue Ridge Mountains! Located midway on the Brew Ridge Trail, but 500 yards off the byway, so guests have a quiet retreat. Perfect for romantic getaways, destination telework space, or families exploring this outdoor paradise community. Stunning property boasts beautiful vistas with sweeping 300-degree mountain and a year-round calendar of outdoor activities. GAS FIREPLACE/FIREPIT

4.99 out of 5 average rating, 155 reviews

A firepit area features several Adirondack chairs arranged around a sandy circle. Natural rock formations and a lush tree line create a serene backdrop, framed by expansive mountain views in the distance.

Chalet in Afton

Elk Mountain Overlook: Breathtaking Views

Mountaintop overlook with jaw dropping views and camp themed interior design. Perched upon Elk Mountain just off the Blue Ridge Parkway this petite chalet is under 30 min from Charlottesville, 10 min to 151 vineyards/breweries/cideries, and 10 min to Waynesboro. Relax in this natural retreat featuring 2 king bedrooms, 2 person soaker tub, double headed shower, and ample kitchen w/many extras. Take in the views from the large deck, firepit, under porch swing, or mountainside adirondack chairs.

4.98 out of 5 average rating, 189 reviews

Rolling green fields are framed by colorful trees in autumn hues, creating a serene landscape. Horses are seen grazing near a small shelter, with distant hills providing a picturesque backdrop under a soft sky.

Apartment in Afton

Cozy stay with scenic views on a horse farmette

Cozy apartment with beautiful views on a horse farmette on the most scenic road in the county. Located within 15 miles from Charlottesville and only 6 miles from Shenandoah National Park and the Blue Ridge Parkway, this vacation rental is the perfect spot if you are looking for places to hike, scenic drives or visit the many wineries, breweries or cideries located in close proximity. The apartment is situated over the garage and has its own separate entrance offering guests plenty of privacy.

Guest suite in Waynesboro

A spacious front porch is adorned with vibrant flowers in various shades, creating a welcoming environment. Comfortable seating is arranged to invite relaxation, while lush greenery provides an enhanced view of the surrounding area. A patterned outdoor rug complements the serene setting.

4.99 out of 5 average rating, 406 reviews

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 unique octagonal house is framed by lush greenery, showcasing its distinctive architecture. A spacious deck offers a vantage point for enjoying unobstructed views of the surrounding landscape. Panoramic windows reflect the natural beauty of the Blue Ridge Mountains, inviting light into the living space.

4.99 out of 5 average rating, 103 reviews

Mountain Overlook House - Blue Ridge Parkway

Unique octagonal house with stunning views of the Blue Ridge Mountains of Virginia. Located 2 miles from I-64, 15 minutes to downtown Waynesboro and an easy 25 min drive to Charlottesville and UVA. Open floor plan, perfect for gathering, and long-range 180 degree views from nearly every room. Fully equipped renovated kitchen. Quality linens and bedding. Rustic, yet modern decor. Home features large fireplace, outside fire pit, wifi, and board games galore. Stargazing and birdwatching heaven.

4.97 out of 5 average rating, 181 reviews

The image showcases a cozy front porch featuring two rocking chairs, perfect for enjoying mountain views. The living area displays a comfortable couch and a stylish coffee table. A private hot tub is visible on the rear deck, complemented by scenic outdoor seating arrangements.

Cottage in Afton

Cottage on 151 w/ Hot Tub, Firepit, Mountain Views

Welcome to Towler Cottage, a getaway in the heart of Route 151 in Afton. The cottage is within minutes from the best wineries and breweries, great local trails, and the Blue Ridge Parkway! Relax in the hot tub on the rear deck, or sit out by the fire pit and gaze at the stars. Enjoy great mountain views from the front porch rocking chairs. With one bedroom with a queen bed, plus a pull-out couch in the living room, the cottage is perfect for couples. Located 25 minutes from Charlottesville.

5 out of 5 average rating, 984 reviews

A serene landscape showcases rolling hills adorned with autumn foliage. In the foreground, tall grass and scattered trees lead to a cozy house perched on a hillside, surrounded by vibrant fall colors. The distant mountains create a peaceful backdrop.

Yurt in Afton

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!

4.99 out of 5 average rating, 246 reviews

A charming bungalow exterior is showcased, featuring a wraparound porch with seating. Surrounding greenery, including bushes and grass, enhances the outdoor appeal. The structure is painted in a dark hue with wooden accents, complementing the clear blue sky.

Bungalow in Afton

The Bungalow at Afton Mountain Retreat by Veritas

Welcome to The Bungalow at Afton Mountain Retreat in the heart of Brewery Trail/Route 151, Vineyard country and the foothills of the Blue Ridge Mountains. The Bungalow is located 1/4th 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.

Superhost

The exterior of the cottage features a welcoming porch with two seated chairs and a wooden railing. Lush greenery and trees surround the cottage, complemented by a beige wooden fence that offers privacy. A clear blue sky brightens the scene, enhancing the inviting atmosphere.

Bungalow in Waynesboro

4.89 out of 5 average rating, 328 reviews

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!

4.99 out of 5 average rating, 373 reviews

Cabin in Vesuvius

The Sanctuary

Nature lovers paradise! Named "The Sanctuary" for the place you can UNPLUG, unwind & find your peace! Perched up high on nearly 60 acres- you are sure to get fresh air & the rest you are searching for! Only 4 miles to Wintergreen, 6 miles to Sherando lake and backs up to the Blue Ridge Parkway there are plenty of things to do OR just relax and enjoy the crickets & stars! With crazy careers, growing kids & constant hustle- everyone needs a hide out like this every now and then!

4.91 out of 5 average rating, 680 reviews

An interior view showcases a cozy living space with wooden walls and ceiling, abundant natural light from large windows, and a ceiling fan. A gray sofa is complemented by a colorful throw blanket, while a small dining area with bright chairs is positioned nearby.

Guesthouse in Afton

Your Perfect Blue Ridge Mountain Hideaway near 151

A luxury tiny home built without compromise. This six-figure, custom-built retreat features high-end finishes, premium materials, and a refined layout that feels both elevated and comfortable. Set in the Blue Ridge Mountains, it offers privacy and tranquility with easy access to scenic drives, hiking, renowned breweries, and local wineries—ideal for a relaxed weekend escape focused on slowing down, good food and drinks, and returning home refreshed.

4.93 out of 5 average rating, 382 reviews

A charming white bungalow is shown, featuring a welcoming yellow front door and dark shutters. Sunlight filters through the trees, highlighting the neatly landscaped front yard and walkway leading to the entrance.

Bungalow in Waynesboro

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.

Popular amenities for Waynesboro outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

4.95 out of 5 average rating, 102 reviews

A modern kitchen features light-colored cabinetry and open shelving. A stainless steel refrigerator and dishwasher are visible, alongside a double sink beneath a window. A round glass dining table is set with black chairs, while decorative items and utensils are neatly arranged on the shelves.

Home in Staunton

Queen City Cottage - Walk Downtown

The modern cottage features a light-colored exterior with large windows and a red front door. A wooden deck extends from the entrance, surrounded by lush green grass and trees displaying autumn leaves in shades of orange and yellow.

4.98 out of 5 average rating, 111 reviews

Cottage at Mountain View Meadow

4.88 out of 5 average rating, 117 reviews

A cozy living room features a classic brick fireplace surrounded by comfortable seating. A colorful area rug adds warmth, while large windows offer views of the greenery outside. Adjacent, a vibrant game room contains a foosball table and warm lighting, ideal for entertainment.

Home in Waynesboro

Gameroom~Gym~Walk to River & Downtown~Nat Park 5mi

4.89 out of 5 average rating, 184 reviews

Home in Grottoes

New modern ranch house in adorable small town

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.

4.98 out of 5 average rating, 122 reviews

Perfect getaway among the orchards of Batesville

Superhost

4.88 out of 5 average rating, 123 reviews

Fox Hill: Hot Tub, Views, Pet Friendly!

5 out of 5 average rating, 214 reviews

The front exterior of the house is shown, featuring a warm brick facade and a sloping lawn. A welcoming front porch is visible, adorned with a seasonal wreath. Large windows allow for natural light, and a pathway leads to the entrance.

Home in Lovingston

Ms Maria's Place - make yourself at home, relax!

4.9 out of 5 average rating, 125 reviews

The open living area features high ceilings and large windows, allowing natural light to enhance the space. A comfortable seating arrangement includes a sofa and two armchairs, while an adjoining kitchen is visible in the background, equipped with modern appliances.

Home in Nellysford

Mountain Bauhaus | Sleeps 8 | Amenities | Grill

Apartment rentals with outdoor seating

A welcoming entryway is presented with floral wallpaper and green wainscoting. A small armchair, paired with a decorative lamp and side table, creates a cozy reading nook. Artwork is hung on the walls, and a door leading to the outside is visible at the end of the hallway.

5 out of 5 average rating, 220 reviews

Queen City Hideaway

The exterior of the building displays a two-story structure with light brown siding and a front porch adorned with white railings. Windows are visible on both levels, complemented by a small garden and walkway leading up to the entrance.

4.94 out of 5 average rating, 175 reviews

Walker's dream. Close to downtown.

Apartment in Stanardsville

A vibrant sunset illuminates the sky with shades of orange and pink, casting a warm glow over the rolling hills. Lush greenery is visible in the foreground, complemented by scattered trees and shrubs, offering a serene view of the surrounding landscape.

4.97 out of 5 average rating, 237 reviews

Parker Mountain Carriage House Near SNP, UVA & JMU

A vibrant living room features a brick accent wall with the word 'STAUNTON' displayed prominently. The space includes a cozy sofa, a wooden coffee table, and accent chairs with bold patterns. Natural light enters through windows, enhancing the braided area rug underfoot.

4.97 out of 5 average rating, 383 reviews

The Shenandoah Suite: Private Balcony, Walkable

4.98 out of 5 average rating, 226 reviews

A bright and airy living area is highlighted by large windows offering mountain views. A casual seating arrangement features a light-colored sofa and a wooden dining table surrounded by black chairs. Sliding glass doors provide access to an outdoor deck.

Apartment in Rockfish

Blue Ridge Bliss - For family & friends to enjoy!

4.92 out of 5 average rating, 210 reviews

Apartment in Rochelle

1 Bedroom Apartment With a Kitchenette on 28 Acres

4.98 out of 5 average rating, 200 reviews

An inground swimming pool is set against a backdrop of lush greenery and rolling hills. The pool's curved shape is highlighted by a stone patio, and boulders are placed at the water's edge. The sky is partly cloudy, allowing soft sunlight to illuminate the scene.

Apartment in Afton

Mountain View Getaway

A bright living area is highlighted by a sunny yellow couch, positioned next to a cozy dining space. A small round table is accompanied by four sleek chairs. Natural light fills the room through large windows, while a decorative rug adds warmth to the wooden floor.

4.95 out of 5 average rating, 279 reviews

Bee & Key—Staunton downtown

Condo rentals with outdoor seating

A spacious living area features a wood-burning fireplace surrounded by light-colored walls. A comfortable couch, adorned with a welcoming throw pillow, faces a wooden coffee table. Natural light enters through large windows, offering views of the outdoor greenery.

4.93 out of 5 average rating, 254 reviews

Where the Trail Ends

An inviting living space features a comfortable sectional sofa arranged around a round coffee table, complemented by a cozy rug. A gas fireplace is framed by white paneling, and large windows provide ample natural light while showcasing views of the surrounding landscape.

4.95 out of 5 average rating, 152 reviews

All-Season 2bd/2ba next to Spa view of Golf Course

A cozy living area features a teal sofa with a yellow accent pillow and a light wood coffee table. The kitchen is adjacent, showcasing modern appliances. Stairs lead to the loft bedroom. Artwork hangs on the wall, and natural light enters through high windows.

4.95 out of 5 average rating, 175 reviews

Ski-In Ski-Out ~ Mtn Views ~ King Suite

A living room features a stone fireplace with a wooden mantel. A clock is mounted above, and decorative items are displayed on the mantel. Hardwood flooring complements the room's layout. The space is open to a kitchen area, visible in the background, with light cabinets and appliances.

4.98 out of 5 average rating, 120 reviews

Wintergreen Resort King bed, Fire place, 2 Bd/2 Br

Superhost

A cozy living area features natural stone accents around a wood-burning fireplace. A small dining table with two chairs is positioned near large windows, allowing ample natural light. Green accent walls enhance the inviting atmosphere, while a comfortable seating area is visible nearby.

4.89 out of 5 average rating, 218 reviews

Tips Up: Cozy Slopeside Retreat w/ Fireplace

A serene landscape captures the sun setting behind distant mountains, surrounded by an expanse of trees and valleys. Soft rays of light break through the clouds, illuminating the sky with warm, golden hues. The atmosphere presents a peaceful retreat into nature.

4.88 out of 5 average rating, 181 reviews

Wander Lodge: Golf, Spa, Wine, or just a getaway

A private balcony features wooden railings, with a light dusting of snow on the ledge. Lush pine trees stand prominently in the background, contrasting against a clear blue sky and hints of distant landscape, contributing to a serene outdoor viewing experience.

4.97 out of 5 average rating, 172 reviews

2-min drive to resort, Outdoor HOA pool now open!

A glass of white wine is positioned in the foreground, capturing the warm hues of a sunset. The sun's golden rays reflect off the wine, while silhouettes of trees and distant mountains create a tranquil backdrop in the evening sky.