Holiday rentals with outdoor seating in Charlottesville

5 out of 5 average rating, 248 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, 150 reviews

Downtown Retreat | Fenced Yard + Pets Welcome

Peaceful North Downtown retreat just minutes from UVA, Downtown Charlottesville, Martha Jefferson Hospital, Virginia’s Wine Trail, and the Blue Ridge Mountains. This bright, single-level, pet-friendly home sleeps up to five guests and features a private fenced backyard with a fire pit and grill, a fully equipped kitchen, high-speed Wi-Fi, and a newly renovated spa-inspired bathroom. Whether you’re visiting for a UVA weekend, wine tasting, work, or a relaxing getaway, you’ll feel right at home.

4.99 out of 5 average rating, 106 reviews

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.

Home in Afton

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.

5 out of 5 average rating, 238 reviews

Home in Greenwood

Gorgeous Modern Mountain Home + Blue Ridge Views

GREENWOOD VISTA - Escape to our modern mountain home 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, 184 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, 231 reviews

The dark wooden cabin, framed by lush greenery, sits at a hillside location with panoramic mountain views. A deck extends from the cabin, featuring a hanging basket chair. A warm sunset casts a golden hue across the sky, enhancing the serene atmosphere.

Cabin in Free Union

Shenandoah Stargazer with Sauna

Stargazer is the perfect place to get away from it all! The stillness and serenity of being nestled in a bird and wildlife sanctuary is so good for your soul. Watch the sunrise from a hanging basket chair at 2700 feet of elevation, or wait for moonrise and toast spectacular star views! Relax in the sauna after a day filled with hiking and an al fresco meal on the deck. Roast s’mores at the deck fire table or over the side yard fire pit. There's magic in the air at this mountaintop retreat!

4.99 out of 5 average rating, 247 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.

4.95 out of 5 average rating, 133 reviews

The exterior of the Ivy Rose Cottage features a rustic wooden facade with a steeply pitched roof and unique architectural elements, including arched windows. Surrounding greenery enhances the rural setting, while a gravel pathway leads to the inviting entrance.

Cabin in Charlottesville

Ivy Rose Cottage nestled b/t Cville & Vineyards

The Ivy Rose Cottage bestows an exceptional ambiance that will captivate your heart. Whisk yourself away to this two bedroom cottage located in Ivy halfway between the Shenandoah Park/Brewery Trail and Charlottesville, home of UVA. The Ivy Rose Cottage, designed and handbuilt by the hosts, is an enchanting mix of cypress, timber frame, copper trellis work, pergolas and other architectural treasures. Fully equipped kitchen and a washer/dryer for those lengthier stay conveniences.

4.99 out of 5 average rating, 161 reviews

An outdoor tub is positioned on a stone patio, surrounded by wooden fencing. Glass doors reveal a cozy bedroom with warm textiles. Soft lighting enhances the space, while a small table nearby holds two glasses and a bucket, inviting relaxation.

Cottage in Faber

Luxury Cottage | Outdoor Tub + Mountain Views

Soak in a private outdoor bathtub beneath the stars, wake to mountain views from your king bed, and open an entire wall of glass to bring the Blue Ridge Mountains inside. Welcome to The Cottage at Perkins Hollow Retreat! Located in Nelson County, just minutes from the Nelson 151 Brew Trail, award-winning wineries, breweries, hiking, and only 25 minutes from Charlottesville, The Cottage is the perfect destination for a romantic getaway, anniversary, honeymoon, or peaceful retreat.

4.95 out of 5 average rating, 731 reviews

Tranquil Estate, Cottage, Vineyards and C'ville

Guests consistently say the sunsets alone are worth the stay! We've had anniversary trips, proposals, creative retreats, and gal pal gatherings looking for fun. This area boasts award winning vineyards, gardens and history buffs enjoy Monticello and Montpelier. Our peaceful cottage offers the perfect space for couples, creatives, and anyone craving beauty just 10 minutes from downtown C'ville. *Read "Your Property." Pool is available most summer stays. Thank you!

Treehouse in Stanardsville

4.97 out of 5 average rating, 114 reviews

CloudPointe Retreat

Rare Appalachian Treehouse Gem! Luxurious, one-of-a-kind retreat for couples. Elevated tiny house among the treetops, private parking, plush bedroom, sleek bathroom, beautiful kitchenette, loveseat, lounge, private double-level decks, fireside lounging (wood provided), gas grill, and patio with a hot tub! Surrounded by nature, with wineries, hikes, restaurants and shopping all nearby. Please come and relax and revel in the beauty of nature! 4WD is recommended.

A spacious living area features large windows that allow natural light to illuminate the space. A comfortable gray sofa and black leather couch are arranged around a central coffee table. Plants add greenery, while a chandelier provides a touch of elegance above.

4.94 out of 5 average rating, 357 reviews

The Octagon ~ bright/spacious 2BR Downtown Retreat

Bright and spacious two bedroom apartment with ample free off-street parking, two blocks from the Historic Downtown Mall. Walk to shops, restaurants, coffee, yoga, and music venues. 10 minute walk ~ the historic downtown mall 5 min ~ Rivanna River - walking trail and tubing/kayaking/SUP 5-10 min ~ UVA 5-10 min ~ Monticello Trail 10-15 min ~ Monticello 15-30 min ~ MANY popular wineries, breweries, and hiking in the Blue Ridge Mountains

Popular amenities for Charlottesville outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

A single-story home with light blue siding is set against a clear sky. A vibrant door adds a pop of color to the entrance, which is framed by landscaped flower beds. A paved walkway leads up from the driveway, inviting visitors towards the front entrance.

4.98 out of 5 average rating, 145 reviews

3BR / Pets Welcome / Fenced Yard / Fiber Internet

4.93 out of 5 average rating, 138 reviews

The Ordinary is surrounded by a spacious lawn, framed by trees and greenery. A small outbuilding is visible to the left, while the house features a welcoming porch and a pitched roof. Natural light brightens the exterior, emphasizing its classic Virginia charm.

Home in Barboursville

Historic 1790 House Near Charlottesville

The exterior of a two-story colonial-style house is visible, showcasing a well-maintained front yard with mature greenery. A gravel driveway leads to a covered parking area. Bright blue skies and scattered clouds frame the scene, highlighting the peaceful, natural surroundings.

4.98 out of 5 average rating, 183 reviews

Wakefield Ct | Private Parking spots | Fast WiFi

The exterior of the guesthouse is presented, featuring a light gray facade and landscaping that includes manicured grass, shrubs, and colorful flower beds. A brick walkway leads to the entrance, which is framed by large windows and a welcoming front door.

4.95 out of 5 average rating, 126 reviews

Unit 4 - Luxury King Suite with Private Balcony

Superhost

4.95 out of 5 average rating, 456 reviews

Walk DT | Pets | Soaking Tub | Parking

4.98 out of 5 average rating, 122 reviews

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.

Home in Afton

Perfect getaway among the orchards of Batesville

4.93 out of 5 average rating, 307 reviews

A charming cottage with a metal roof features a welcoming front porch, surrounded by greenery. Rocking chairs offer a cozy spot, while stone pathways lead to a landscaped yard. Light spills onto the deck from nearby trees, blending indoor and outdoor spaces harmoniously.

Home in Barboursville

Spaniel Hill; cozy hilltop home w privacy & views

An open living area is highlighted by a light-colored sofa and a wooden coffee table. A spiral staircase leads to an upper loft, while a dining table with wooden chairs sits nearby. Large windows provide ample natural light, illuminating the space.

4.98 out of 5 average rating, 617 reviews

The Loft at Minor Mill - Private loft apartment.

Apartment rentals with outdoor seating

Apartment in North Downtown

A living room featuring a classic tiled fireplace with an electric insert, surrounded by dark wooden paneling. A cozy red trunk and a wooden chair complement the space, while a patterned rug adds warmth. Glass display cabinets showcase decorative items, enhancing a historic ambiance.

4.91 out of 5 average rating, 415 reviews

Boho Vibe: Walkable, Quiet, Historic Downtown

A well-lit living area features a comfortable sofa, two patterned chairs, and a coffee table. A television is placed on a white entertainment unit, while soft lighting from nearby lamps creates a cozy ambiance. Light wood flooring complements the neutral color scheme.

4.84 out of 5 average rating, 242 reviews

Private, Clean, Central, Spacious - UVA/Downtown

A bright living area features large windows allowing natural light to fill the space. A comfortable white couch is paired with a maroon ottoman and a dining table with chairs. Framed artwork adorns the walls, adding character to the room.

4.84 out of 5 average rating, 825 reviews

Belmont Loft· Walk Downtown· Work or Wine Weekends

A bright living area features a striped sofa adorned with green and gold cushions. A wooden coffee table sits in the center, complemented by a soft armchair nearby. Natural light filters through two windows, casting a warm glow on the decor, including framed artwork and a large flat-screen TV.

4.98 out of 5 average rating, 270 reviews

Belmont BnB ~ 2BR/1BA ~ Comfort & Convenience

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

4.98 out of 5 average rating, 201 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

4.95 out of 5 average rating, 287 reviews

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.

Apartment in Staunton

Bee & Key—Staunton downtown

A modern living area features a gray couch adorned with red accent pillows. A colorful abstract wall art hangs above a white media console, which holds a television. The kitchen area is visible in the background, complemented by red bar stools and wooden cabinets.

4.91 out of 5 average rating, 878 reviews

Modern Belmont home - steps from Downtown Mall!

Condo rentals with outdoor seating

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, 154 reviews

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

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, 358 reviews

Five Minute Walk to Everything!

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, 176 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, 121 reviews

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

4.97 out of 5 average rating, 176 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, 165 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.

4.99 out of 5 average rating, 274 reviews

Panoramic Sunsets Mountain Views Pool $99 Midweek

A cozy living area features soft sofas arranged around a wooden coffee table. A stone fireplace occupies one wall, with a fire burning brightly. Large windows provide natural light and a view of the surrounding landscape.