House holiday rentals in Charlottesville

4.97 out of 5 average rating, 147 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

We welcome you to our new modern house (2020) located on 52 private wooded acres, adjacent to our winery and the Blue Ridge. Designed and built by award winning Architect and wine maker, Barry Moss, it is gorgeous inside and out. Decks overlook the river, forest and mountain farms. A path leads down to the river beach. Walk up to the top of the mountain and experience the best wines and views of any winery in Virginia. Modern interiors with wood floors, granite counters, and tiled bathroom.

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A serene view of the Blue Ridge Mountains is presented, showcasing rolling hills blanketed in mist during sunrise. The sky is painted with soft pastel shades of orange and pink, highlighting the natural beauty of the surrounding landscape.

4.98 out of 5 average rating, 129 reviews

Mountain Mama- Amazing Views! + Hot Tub!

MOUNTAIN MAMA - The home for gorgeous Blue Ridge Mountain views : ) Situated on a graceful 26 acres minutes off Rt. 151, our mountainside home is nestled within the beautiful Rockfish Valley and offers incredible views from every window in a truly unique and newly renovated home. Enjoy sunsets over 3600’ Humpback Mountain due west and sunrises lighting up the valley ridges. If you need time to be inspired by nature’s beauty, this home offers a rare breath of fresh air! Book your stay today!

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The exterior of the West Wing showcases a welcoming entrance with a vibrant pink door. Steps lead up to the porch, which is surrounded by lush greenery and potted plants. The house's architecture features a combination of siding and a screened-in area, blending with the mature garden.

4.91 out of 5 average rating, 321 reviews

West Wing

Quiet West Wing of my home, was newly renovated February 2020. The West Wing has a private entrance set in a mature garden. Two bedrooms upstairs sleep up to four people. One w/queen size bed and views of the garden.The 2nd has 1 full and 1 twin bed, plus walkout balcony. Each floor has a full bath. The 1st floor has a combined living room/dining area with a counter, bar sink, microwave, coffee maker, toaster oven andTV. Pet dogs only are welcome. The cleaning fee is included in the base price

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4.93 out of 5 average rating, 311 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

Cozy hilltop with Views, deck and hot tub. Cottage furnished with original art and antiques collected by us, the cottage is easy to get to but feels like a world away. Recently renovated main level has three cozy bedrooms and 1.5 baths, sleeps 6, and the garden level suite offers one large king bed and a twin bed with full bath and separate sink area, sleeps 3. Close to UVA, Pantops 250 corridor, theDowntown Mall, Gordonsville and Orange to our north. Over 20 highly rated wineries within 20 m

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4.99 out of 5 average rating, 153 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.

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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, 107 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.

LocationFamilyQuiet

5.0 out of 5 average rating, 239 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.

LocationFamilyDecor

4.96 out of 5 average rating, 354 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

Iconic home and Farm in Dyke, Virginia, circa 1891. Situated on the Roach River with views of the Blue Ridge mountains and pastures. Relax on one of the double porches or under on of the shade trees. The stone fireplace warms the heart and soul on a cool evening. Minutes from the Shenandoah National Parkway, the Blue Ridge School and several beautiful wineries. Approx. 12 miles from CHO airport, 20 min from Blue ridge Parkway, 10 min. to Standardsville and 20 miles to Charlottesville.

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4.97 out of 5 average rating, 395 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!

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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, 150 reviews

3BR / Pets Welcome / Fenced Yard / Fiber Internet

Sitting atop the neighborhood, Monticello can be seen from our Ridgetop home. Convenient to all parts of Charlottesville, including Downtown, UVA, and Hospitals. Local parks offer swimming, boating, & are all walkable. The fenced yard allows for a safe space for dogs and the private patio is perfect for relaxing. The home offers an open design in the kitchen, living & dining room. Bath has a modern tile with a jacuzzi tub. Fast TING fiber internet. Freshly painted. Big Green Egg grill

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Superhost

4.95 out of 5 average rating, 460 reviews

Walk DT | Pets | Soaking Tub | Parking

The High‑Note Craftsman Cottage – live like a local in downtown Charlottesville Stay in a charming and pet friendly Craftsman cottage just minutes from Charlottesville’s Downtown Mall. Enjoy a soaking tub, fast Ting fiber Wi-Fi, and rare free parking — perfect for couples, families, and remote work travelers. This bright, comfortable home blends historic character with modern amenities, creating the ideal base for exploring Charlottesville, UVA, wineries, and the Blue Ridge Mountains.

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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, 159 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.

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Popular amenities for Charlottesville house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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.

4.92 out of 5 average rating, 239 reviews

Pine Lake Lodge

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A historic two-story estate is visible beyond a cobblestone driveway, framed by lush green trees. In the foreground, a stone statue of a dog holds a basket of fruit, adding charm to the property entrance against a clear blue sky.

4.98 out of 5 average rating, 123 reviews

Rivanna Farm Estate North I Pickleball I Pool

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A functional kitchen with wooden cabinetry and an island is featured. The space includes a stove, modern appliances, and a ceiling fan. A brick wood stove adds a rustic element, while a small plant sits on the island, providing a touch of greenery.

4.94 out of 5 average rating, 160 reviews

Farmhouse on Working Vineyard

LocationFamilyLayout

4.99 out of 5 average rating, 171 reviews

A spacious deck is surrounded by greenery, featuring several black Adirondack chairs arranged around a firepit. The glass railing provides an unobstructed view of the outdoors, enhancing the inviting outdoor space.

Home in Nellysford

151Escape | 5☆ Group Fun! Game Room/Bar/Deck/4kTVs

LocationFamilyBeach

4.94 out of 5 average rating, 252 reviews

An open living area features high wooden ceilings with exposed beams, creating a spacious atmosphere. A large kitchen island with bar seating is situated near a dining table. Two spiral staircases lead to upper levels, while large windows frame views of the surrounding nature.

Home in Robertson

One Of A Kind Home in VA Wine Country on 50 acres

LocationFamilyIndoor spaces

5.0 out of 5 average rating, 110 reviews

A hot tub bubbles invitingly on a concrete pad in a spacious yard. Surrounding the tub is a well-maintained green lawn, with majestic mountains visible in the background. White Adirondack chairs are positioned nearby for relaxing moments outdoors.

Home in Nellysford

Game Room+Screen Porch+Hot Tub+Fire Pit on 151

LocationFamilyPool

4.89 out of 5 average rating, 129 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

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Home in Wintergreen Resort

4.97 out of 5 average rating, 127 reviews

Cliffs Edge -A Contemporary Mountain Home

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Weekly house rentals

4.95 out of 5 average rating, 228 reviews

A single-story house with light yellow siding is framed by neatly trimmed bushes and mature trees. A set of wooden steps leads to the front porch, with a welcoming entrance door in the center. A gravel driveway provides access to the property.

Home in North Downtown

Walk Downtown | Off-Street Parking | Sleeps 6

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Superhost

The living area features a modern sectional sofa in shades of green, accompanied by a glass coffee table. A pair of armchairs provides additional seating. Colorful artwork adorns the walls, complementing the natural light filtering through the windows, with a dining area visible in the background.

4.84 out of 5 average rating, 255 reviews

Mountain View Rambler | 3 Bedrooms | Private deck

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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.

4.97 out of 5 average rating, 186 reviews

Wakefield Ct | Private Parking spots | Fast WiFi

LocationFamilyParking

A spacious deck features a hot tub and a dining area set for six. Scenic views of a vibrant sunset and surrounding landscape create a calming atmosphere, while the wooden decking enhances the connection to nature.

4.95 out of 5 average rating, 144 reviews

Sycamore Shade: 151 House, HOT TUB, Mountain Views

LocationValueBarbecue

A cozy brick house features a welcoming front deck set against a backdrop of lush greenery. A large window is visible, allowing natural light to fill the interior. Flowering shrubs and tall grass surround the entrance, highlighting the home's inviting exterior.

4.96 out of 5 average rating, 224 reviews

Cozy 3 bedroom home near UVa and Downtown Mall.

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4.93 out of 5 average rating, 166 reviews

A bright bedroom features a spacious bed adorned with coral floral bedding. Two bedside tables with lamps are positioned on either side, providing soft illumination. Above the bed, three narrow windows allow natural light to fill the room, creating an airy atmosphere.

Home in North Downtown

The Carriage House at Wine Cellar Circle

ValueFamilyCleanliness

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.

5.0 out of 5 average rating, 208 reviews

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

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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, 124 reviews

Perfect getaway among the orchards of Batesville

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Private house rentals

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.

5.0 out of 5 average rating, 112 reviews

Downtown living

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A spacious living area displays soft beige sofas paired with dark blue accent tables. Natural light filters through large windows, enhancing the warm, neutral tones of the walls. A glimpse of the kitchen and bedroom can be seen through open doorways, providing a sense of flow.

4.96 out of 5 average rating, 222 reviews

Woodwind Cottage

LocationFamilyNearby

4.92 out of 5 average rating, 119 reviews

Charlottesville Bungalow close to UVA

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An inviting outdoor space features a hot tub surrounded by a spacious deck, with mountain views in the background. A large dining table with wooden chairs is positioned indoors, complemented by a fully-equipped kitchen visible in the adjacent area. A cozy fire pit with adirondack chairs provides a warm setting.

4.99 out of 5 average rating, 154 reviews

Hot Tub, Firepit, Mtn Views, Walk to Coffee & Park

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A panoramic view reveals rolling hills and a vibrant landscape adorned with autumn foliage. Lush green fields stretch towards the horizon, bordered by trees displaying a spectrum of fall colors under a clear blue sky.

4.95 out of 5 average rating, 143 reviews

Scenic Private Farm House Great for Large Groups

LocationValueWi-Fi

4.98 out of 5 average rating, 132 reviews

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

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The two-story house features a white exterior with dark shutters and a welcoming front porch. A gently sloped lawn surrounds the home, leading to mature trees and a scenic backdrop. The roof is accented with three gabled dormer windows, adding character to the facade.

4.98 out of 5 average rating, 191 reviews

Clean family-friendly 5br for wine country getaway

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A spacious living area features natural wood paneling and a mix of modern and vintage furnishings. Soft light from pendant lamps highlights a green sofa and an orange chair. Plants are strategically placed, adding a touch of nature to the inviting atmosphere.