Holiday rentals with outdoor seating in Waynesboro

5 out of 5 average rating, 243 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

4.88 out of 5 average rating, 112 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

Centrally located historic home walkable to river, downtown shops & restaurants. Less than 15 mins to Shenandoah Natl Park, Blue Ridge Pkwy, Skyline Drive, Blue Ridge Tunnel Hike, Basic City Brewery, The Foundry, Wineries, Antique shops & Augusta Expo. Charlottesville, Staunton, Harrisonburg & Nelson Ski/Wineries 30mi The rec center across the street has playground & basketball court. Home has a main level bed & bath, game room, gym, 2 living rooms, firepit, fireplace, king bed & lots of charm!

4.98 out of 5 average rating, 298 reviews

The cottage is framed by lush greenery and trees, showcasing rustic wooden siding and a steeply pitched roof. Large windows allow natural light to fill the interior. A pair of rocking chairs is situated on the porch, inviting relaxation in a serene outdoor setting.

Cottage in Afton

Oasis in the Blue Ridge Rt. 151 Brew Ridge Trail

Welcome to the Glass Hollow Cottage! Come make yourself at home and enjoy the rustic charm of our custom hand-built cottage. A perfect getaway for a couple or friends who want a 1-of a-kind destination. Adventure and R & R await you!!! Enjoy the well stocked kitchen & the bright, clean, cheery ambience.... everything you need to feel at home & then some. Prime location: Just minutes to Rt. 151/Brew Ridge Trail, dozens of popular wineries/breweries, Wintergreen Resort & Shenandoah Nat. Park.

4.99 out of 5 average rating, 154 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.

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.

4.98 out of 5 average rating, 397 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, 102 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, 174 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.

4.99 out of 5 average rating, 334 reviews

Four horses graze on a lush green lawn, with a charming two-story building in the background. The house features a balcony and is surrounded by blooming shrubs and trees, creating a serene atmosphere on the farm.

Farm stay in Afton

Afton, Mountain View Mini Farm

Welcome to Mountain View Mini Farm! We are located in the Rockfish Valley(Afton, VA)with amazing views of the Blue Ridge Mountains. Our farm is just minutes to wineries, breweries, cideries, Shenandoah National Park and more! There is so much to do close by, but once you get on the farm, you won't want to leave! We have a total of 5 horses, with 3 being mini rescue horses. There's a fire pit area where you can roast S'mores while you watch the sunset. Be sure to look at bedrm 2 description.

4.99 out of 5 average rating, 243 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, 326 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, 372 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!

4.99 out of 5 average rating, 442 reviews

The cottage is framed by tall trees and lush greenery. It features a welcoming front porch with wooden posts, surrounded by well-maintained grass. A glimpse of a rustic barn is visible in the background, adding to the serene farm setting.

Farm stay in Weyers Cave

FarmCottage: Hot Tub Sauna Massage ShenandoahViews

Welcome to the Cottage at Dices Spring Farm. This gem is nestled in the beautiful Shenandoah Valley. You will love the weather-sheltered hot tub building, relaxing greenhouse garden massage space and personal finely crafted sauna with a Sweden built cold shower dump bucket A custom bathroom double-headed shower, and reading nook in the loft are favorites to unwind and disconnect. Minutes away from JMU, Buc-ee's, Valley Pike Market & Vineyards.

Popular amenities for outdoor seating rentals in Waynesboro

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

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, 173 reviews

The Inn at Blue Mountain Brewery

4.96 out of 5 average rating, 100 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

4.94 out of 5 average rating, 159 reviews

A charming three-bedroom home is surrounded by lush gardens filled with colorful flowers and vibrant greenery. Towering hills rise in the background, while a variety of trees and shrubs add to the scenic landscape of the property.

Home in Lovingston

Three Springs with EV charging station

4.94 out of 5 average rating, 371 reviews

Home in Mount Crawford

House on River, HOT TUB, WIFI, Near Buc-ee’s &I81!

4.89 out of 5 average rating, 181 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

4.94 out of 5 average rating, 187 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 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, 118 reviews

Perfect getaway among the orchards of Batesville

The exterior of a charming white building is shown, characterized by sleek lines and stone accents. Symmetrical windows allow natural light to enter, while greenery provides a pleasant contrast against the structure. A gravel pathway leads to the entrance, enhancing the inviting atmosphere.

4.88 out of 5 average rating, 510 reviews

Scenic Barn Escape on 151,Stunning views, Sleeps 6

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, 218 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.

4.93 out of 5 average rating, 169 reviews

Walker's dream. Close to downtown.

4.79 out of 5 average rating, 108 reviews

A warm and cozy bedroom is visible, featuring a spacious bed with yellow pillows and a neutral quilt. A bedside table holds a ceramic cup and a small lamp with a textured shade. Soft lighting enhances the inviting atmosphere against wooden accents and a colorful area rug.

Flat in Afton

Earth Room Suite | Peaceful Blue Ridge Retreat

4.99 out of 5 average rating, 266 reviews

The living area features a light wood floor with a colorful area rug. A blue armchair and a patterned sofa provide comfortable seating. A dining table with black chairs stands nearby, and a small bookshelf holds various games and books. Sliding glass doors offer access to the patio.

Flat in Broadway

Shenandoah Valley apartment with view

4.98 out of 5 average rating, 225 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.

Flat in Rockfish

Blue Ridge Bliss - For family & friends to enjoy!

A Gothic Revival Victorian home from 1877 is surrounded by lush greenery, featuring symmetrical hedges. The two-story house has a gray exterior with decorative rooflines and multiple gabled peaks, complemented by a broad set of steps leading toward the entrance.

4.97 out of 5 average rating, 271 reviews

Updated Victorian Welcomes You & Your Pets

A spacious bedroom features a king bed adorned with colorful pillows and a warm throw blanket. The room is decorated with teal walls, wooden furniture, and a stylish area rug, while natural light flows through the window, complemented by vibrant curtains.

4.97 out of 5 average rating, 139 reviews

Urban Cowboy Suite: Private Workspace, Walkable

4.99 out of 5 average rating, 122 reviews

A bright and airy space is highlighted by large windows that invite natural light. A daybed with plush pillows offers a cozy seating area, while a wooden table adds functionality. Light hardwood flooring complements the warm atmosphere, with greenery visible outside.

Flat in Bridgewater

Big views! - The Loft at Wildwood

Apartment rentals with outdoor seating

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

The two-story condo features a warm wood exterior, framed by lush greenery and trees. Wide wooden steps lead to the entrance, giving access to individual balconies that enhance the inviting appearance of the building.

4.96 out of 5 average rating, 354 reviews

Five Minute Walk to Everything!

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.

4.97 out of 5 average rating, 119 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, 216 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.

4.96 out of 5 average rating, 171 reviews

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

A scenic waterfall cascades down a rocky hillside, surrounded by trees that stretch upward toward the sky. Moss-covered stones are visible in the foreground, adding to the natural setting. Sunlight filters through the branches, illuminating the waterfall's flowing movement.

4.91 out of 5 average rating, 163 reviews

Cozy Comfort with a View - Wintergreen Resort

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.