Holiday rentals with outdoor seating in Charlottesville

5 out of 5 average rating, 235 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

5 out of 5 average rating, 154 reviews

A charming cottage is nestled among lush green grass and surrounded by trees. Its metal roof and white siding are complemented by well-maintained shrubbery. Dappled sunlight filters through the tree branches, creating a serene outdoor ambiance.

Cottage in Covesville

Historic cottage with stunning mountain views

Welcome to Rose Cottage in picturesque Albemarle County, where you'll enjoy expansive 360-degree views of the mountains surrounding historic Cove Lawn Farm. Relax in the tranquil rural setting or stroll more than two miles of comfortable walking paths that wind through 25 acres of stream-lined hayfields. From Rose Cottage, you're just minutes from the best local cideries, distilleries, and wineries including Pippin Hill Farm & Vineyards. Easy 20-minute drive to UVa and 22 minutes to Monticello.

5 out of 5 average rating, 228 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.

4.99 out of 5 average rating, 149 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.

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, 172 reviews

Wakefield Ct | Private Parking spots | Fast WiFi

BRAND NEW LISITING! Cozy stay in an updated colonial style house on a quiet street. Short drive from great local spots along Downtown Cville, UVA Corner, Monticello, Blue Ridge Parkway, The Appalachian Trail, breweries and local wineries. An excellent choice for hosting small gathering with good yard space and pouch. A wonderful stay if you like to be close to all the attractions Cville has to offer, but still far enough to enjoy peace and quiet. Thank you, for your time and consideration.

4.99 out of 5 average rating, 209 reviews

The entrance features double wooden doors that open to a welcoming interior. A 'hello' mat is placed on the threshold, and two stylish chairs are positioned on the balcony above, inviting guests to enjoy the view. Lush plants accentuate both sides of the entrance.

Flat in Somerset

Cozy Farm Apt near Cville•wineries, mt. views

Come experience a relaxing getaway on our family’s dairy farm! Set in beautiful Orange County, We are close enough to Charlottesville (25 min) to fulfill all your shopping and eating needs, but have the privacy, calm and tranquility of the country, with beautiful majestic mountain views! This is a wonderful location for exploring all of wine country, unwinding from the hustle of busy life, and then taking in the sunset in this quiet country setting with rolling hills as your backdrop!

4.97 out of 5 average rating, 379 reviews

The image features a charming two-story home surrounded by lush greenery and flowering trees. A circular driveway leads to the entrance, with manicured lawns enhancing the exterior. The backdrop includes rolling hills and bright blue skies, creating a serene and inviting setting.

Home in North Garden

Lux Country Retreat minutes from Charlottesville!

Located just off route 29 this private luxury retreat with surrounding 2 acre fenced yard is one mile from Pippin Hill Farm & Vineyard and only 15 minutes from UVA/Charlottesville. You will find this home spacious, bright and airy, perfect for entertaining groups or families. The house is completely equipped with everything you may need to host the perfect getaway! Nearby attractions: Pippin Hill, Albemarle Ciderworks, Ragged Branch Distillery, Potter's Craft Cider and Charlottesville!

4.99 out of 5 average rating, 210 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!

4.96 out of 5 average rating, 125 reviews

A rustic cottage exterior is showcased, featuring weathered wood siding and a steeply pitched roof adorned with a central peaked window. Flanking the entrance are symmetrical decorative elements and manicured greenery. The surrounding landscape includes seasonal foliage, enhancing the natural setting.

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.

Cottage in Charlottesville

A serene patio area features a small round table surrounded by two black chairs. Lush greenery and a pathway visible in the background enhance the tranquil setting, with garden views inviting relaxation.

5 out of 5 average rating, 187 reviews

Honey B - Beautiful small house 9 minutes from UVA

Best of both worlds! In beautiful nature but close to UVA, Monticello and downtown. Honey B (Honey House 2) has a lofty feel with the footprint of a small house. High ceilings and several skylights allow for light and privacy in the quiet neighborhood, Located on the southwest side of Charlottesville, just 7 minutes to Scott Stadium, UVA campus, and restaurants, 10 minutes to historic downtown mall, Thomas Jefferson’s Monticello and central to many major wineries and breweries.

A welcoming exterior of a curved house is presented, featuring a light stone pathway leading to a front porch. Two white rocking chairs are positioned in front, with decorative planters filled with greenery on either side. The backdrop consists of lush trees and a blue sky.

4.97 out of 5 average rating, 147 reviews

Unit 1_Expansive Luxury Suite for up to 4 Persons

Take a journey to Albemarle County and experience historical sites and luxurious accommodations. Sonsak is uniquely situated on the Thomas Jefferson Parkway; nears area's most celebrated landmarks, including Monticello - Home of Thomas Jefferson, directly across Michie Tavern and near Ash Lawn - Home of James Monroe, Carter Mountain Orchard and numerous Vineyards. Embark on a 'Journey Through Hallowed Ground', an unforgettable experience that's packed with history and beauty.

5 out of 5 average rating, 195 reviews

The kitchen features white cabinetry with glass-front doors and a herringbone backsplash. A farmhouse sink sits below a window, complemented by modern appliances, including a gas stove and a stainless-steel dishwasher. Natural light streams in, highlighting the spacious countertop area.

Home in Lewis Mountain

Cavalier Cottage-3 BR/Bath, Calm Amid UVA Grounds

Fully-updated, custom home in premier location. Warm hardwoods, lots of light, comfortable sofas & beds, easy check-in -- we strive to make your stay restful and refreshing. Nestled between Scott Stadium & JPJ, O'Hill & the Rotunda, wine country & the downtown mall, you could not be closer to the action yet in a quiet, residential neighborhood. The perfect place for any & all Cville/UVA events, work trips, reunions, weddings, family vacations, college visits, etc.

Popular amenities for outdoor seating rentals in Charlottesville

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

4.98 out of 5 average rating, 105 reviews

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.

Home in Afton

Cottage at Mountain View Meadow

An open-concept living space is featured, showcasing a cozy seating area with a light grey armchair and a small side table. A dining table with black chairs is visible in the background, along with dark cabinetry and decorative items on display.

4.98 out of 5 average rating, 130 reviews

Rooftop*Mountains*Lake/Near Monticello/DT/Wineries

A bright bedroom features a spacious bed layered with white bedding and a navy throw blanket. Two bedside tables with lamps are positioned next to the bed. Natural light enters through two windows, and a colorful artwork of the Eiffel Tower decorates the wall above.

4.93 out of 5 average rating, 147 reviews

Avon House | Bright Large Family Home

4.96 out of 5 average rating, 343 reviews

A spacious, two-story house with white siding and large porches is featured. Lush green grass surrounds the structure, and the landscape includes open pastures and trees. The setting is serene, with plenty of natural light illuminating the exterior.

Home in Dyke

Living Water Farm, Blue Ridge

A contemporary two-story house features a gray exterior with multiple windows of varying sizes. The front porch is accessed by a small set of stairs, and a blue front door adds a pop of color. A driveway accommodates a parked vehicle beside landscaped bushes.

5 out of 5 average rating, 107 reviews

Downtown living

4.97 out of 5 average rating, 113 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

4.97 out of 5 average rating, 139 reviews

A modern house is nestled within a lush forest, partially hidden by tall trees. Large glass windows reflect the surrounding greenery, while a spacious deck extends from the structure, offering a view of the forest floor. The entrance is accessed via a gravel pathway.

Home in Dyke

Moss Vineyards Lodging

4.9 out of 5 average rating, 105 reviews

Cozy Downtown Cottage!

Apartment rentals with outdoor seating

Superhost

An open concept living area showcases wooden beams and heart pine floors. A cozy armchair with a floral pattern introduces color, while a desk and chair provide a workspace. The kitchen area features stainless steel appliances and an inviting countertop, fostering a warm communal space.

Flat in Fifeville

4.78 out of 5 average rating, 302 reviews

Classy new renovation in Fifeville

4.91 out of 5 average rating, 406 reviews

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.

Flat in North Downtown

Downtown Mall & Monticello-Celebrate America's 250

4.83 out of 5 average rating, 812 reviews

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.

Flat in Charlottesville

Belmont Loft· Walk Downtown· Work or Wine Weekends

4.98 out of 5 average rating, 255 reviews

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.

Flat in Charlottesville

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

4.97 out of 5 average rating, 234 reviews

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.

Flat in Stanardsville

Parker Mountain Carriage House Near SNP, UVA & JMU

4.98 out of 5 average rating, 220 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!

4.96 out of 5 average rating, 247 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.

Flat in Staunton

Bee & Key—Staunton downtown

4.95 out of 5 average rating, 419 reviews

Flat in Staunton

Travelers Nook - close to downtown

Apartment 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, 253 reviews

The Modern Mountain Condo

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, 350 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.

4.96 out of 5 average rating, 169 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.

4.97 out of 5 average rating, 118 reviews

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

4.9 out of 5 average rating, 146 reviews

Panoramic Peak: Wintergreen Condo with Views

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, 167 reviews

2-min drive to resort, Outdoor HOA pool opens 5/25

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, 161 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.