House holiday rentals in Charlottesville

4.93 out of 5 average rating, 295 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

5 out of 5 average rating, 226 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.

5 out of 5 average rating, 114 reviews

A comfortable living area features a gray sofa adorned with patterned throw pillows. A modern table sits in front, displaying a potted plant and a decorative tray. Colorful artwork hangs above the sofa, while a lamp provides soft lighting in the corner.

Home in Keswick

One Level Living at Shadwell Terrace

Set in the heart of Wine Enthusiast’s Wine Region of the Year, this newly renovated 2-bedroom, 800 sq/ft terrace level flat with separate entrance, is located in a private setting in the Keswick area. Close to Downtown Charlottesville, we are adjacent to Clifton Inn and Glenmore and minutes to Keswick Hall. After exploring many of Virginia’s wineries, breweries, and historical sites, kick your feet up between the trees in the hammock or share your adventures online with our high speed Wi-Fi.

A cozy living area features a mix of comfortable seating, including two armchairs and a sofa with vibrant cushions. A wooden coffee table occupies the center, resting on a patterned rug. Large windows allow natural light to fill the space, complemented by wooden accents and a ceiling fan.

4.96 out of 5 average rating, 416 reviews

Beautiful Sunny 1 bedroom Home In Charlottesville

Bright clean and sunny small HOUSE with hardwood floors and high ceilings. Walk to the downtown mall and concert pavilion in less than 10 minutes. Or just enjoy neighborhood restaurants and bars right here in historic Belmont. 2 minutes walk to Mas, Tavola, The Local, Junction, Belle coffee , Beer run and BBQ. Very close to highway 64 Monticello and all vineyards. Private driveway cable tv WiFi and all amenities. If you’re looking for longer than 5 days or even several months just contact me.

4.97 out of 5 average rating, 110 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

Unwind at this very special oasis, highly rated by our guests! Stillhouse Creek Cottage has everything you need: large kitchen, dining nook, living room with queen sofa bed, and two bedrooms with queen and king beds. The outdoor deck is perfect for sitting and dining under the sun and the stars, with a view for miles. Relax at night in the hot tub! When you’re ready to explore, hike on nearby Appalachian Trail, swim the local reservoirs, and visit many close-by wineries, breweries and music!

4.97 out of 5 average rating, 375 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!

4.95 out of 5 average rating, 151 reviews

Belmont Private Suite, 1/2 mile to Downtown Mall

Cozy, quiet high-ceiling basement suite located in historic Belmont neighborhood. Private entrance with keypad lock for easy check-in/out. Space includes living area, 1 large bedroom with queen bed (air mattress provided if needed), full bathroom with towels/essentials, coffee maker, electric tea kettle, microwave and mini fridge. Walking distance to Downtown mall and numerous restaurants, coffee shops, and parks nearby. 1-2 mile walk from UVA and 3 miles to Monticello. Free street parking.

4.97 out of 5 average rating, 116 reviews

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.

Home in Woolen Mills

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

4.95 out of 5 average rating, 433 reviews

Home in Woolen Mills

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.

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, 210 reviews

Woodwind Cottage

Woodwind Cottage is a brand new, beautifully built cottage with living room, bedroom, bath, kitchen and loft. It has charming architectural details and a covered porch for enjoying the view of the woods. The loft has a fold out sofa for an extra guest or private work space. The home has wifi, smart tv for streaming, and a gas fireplace. Enjoy reading in the oversized window seat, rise early to see deer in the yard or, perhaps, a hot air balloon overhead in the spring and fall.

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.

4.98 out of 5 average rating, 145 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, 192 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 house rentals in Charlottesville

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Wintergreen Resort

A panoramic view of rolling mountains is framed by lush green treetops. Soft mist blankets the valleys below, gently illuminated by the sunlight above. The vibrant sky showcases clear blue hues with wisps of clouds, creating a serene and peaceful atmosphere.

4.97 out of 5 average rating, 118 reviews

Cliffs Edge -A Contemporary Mountain Home

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.

4.93 out of 5 average rating, 233 reviews

Pine Lake Lodge

4.96 out of 5 average rating, 232 reviews

A private in-ground swimming pool is surrounded by a wooden deck and sun loungers. Shade is provided by a canopy, and lush greenery is visible in the background, highlighting the calming outdoor setting. The pool features a net for recreational activities.

Home in Lovingston

Private Pool Opens April 1 - All Year Hot Tub

4.94 out of 5 average rating, 154 reviews

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.

Home in Afton

Farmhouse on Working Vineyard

4.98 out of 5 average rating, 158 reviews

The entrance to Fairhill Farm is marked by a white wooden sign displaying the name, set against a backdrop of rolling hills adorned with autumn foliage. A vibrant red bush frames the sign, contributing to the natural beauty of the landscape.

Home in Stanardsville

Charming Carrie's Cottage at Fairhill Farm

Home in Wintergreen Resort

A wooden walkway leads to the entrance of the house, framed by vibrant pink rhododendron flowers. Tall trees provide a natural backdrop, with dappled sunlight filtering through the leaves, creating a serene outdoor setting.

4.95 out of 5 average rating, 146 reviews

Bear's Mountain Escape

4.9 out of 5 average rating, 116 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

Superhost

A single-story house with white vinyl siding is surrounded by well-maintained greenery. A front porch features a swing, while large windows invite ample natural light. The muted color palette of the exterior harmonizes with the inviting lawn space, creating a peaceful outdoor setting.

Home in Schuyler

4.8 out of 5 average rating, 117 reviews

Peaceful Cottage

Weekly house rentals

A charming cottage is framed by lush greenery and decorative shrubs. A gently sloping wooden deck leads to the entrance, while a rain barrel is positioned beside the house. The surrounding yard features a well-maintained grassy area and stepping stones that complement the outdoor space.

4.82 out of 5 average rating, 425 reviews

Adorable Downtown Cottage

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.

4.92 out of 5 average rating, 146 reviews

Avon House | Bright Large Family Home

Superhost

A covered deck provides a dining space with a glass top table surrounded by black chairs. The serene view overlooks rolling hills and trees showcasing autumn foliage, creating a tranquil outdoor setting for relaxation and enjoyment.

4.8 out of 5 average rating, 136 reviews

Secluded Home with Mountain Views | 2 Bed, 2 Bath

A modern kitchen is showcased with a central island featuring bar seating. Wall-mounted shelves hold magazines, and a stainless steel refrigerator is located nearby. The entrance door, crafted from wood, allows natural light to brighten the space, contributing to an open and inviting atmosphere.

4.94 out of 5 average rating, 125 reviews

Kid and Family Friendly Downtown

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, 104 reviews

Downtown living

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.

4.85 out of 5 average rating, 231 reviews

Mountain View Rambler | 3 Bedrooms | Private deck

4.99 out of 5 average rating, 889 reviews

A charming cottage with a peaked roof features a welcoming red door. Surrounding gardens with colorful flowers and lush greenery enhance the entryway, while a gravel path leads to the entrance. Trees provide a natural backdrop, contributing to the serene setting.

Home in Keswick

Charming Cottage at Golden Hill

5 out of 5 average rating, 126 reviews

The exterior of a spacious ranch-style home is presented, featuring a welcoming entrance with a landscaped pathway and well-maintained greenery. Flanking the home are ample trees providing shade, set against a blue sky with scattered clouds.

Home in Waynesboro

Beauty in the Shenandoah Valley

Private house rentals

5 out of 5 average rating, 95 reviews

The exterior of the house features a well-maintained façade with light grey siding and black shutters. A welcoming entrance door is flanked by greenery and floral landscaping, set on a lush green lawn, bringing a sense of tranquility to the setting.

Home in Greenbrier

Charming 3 bed/3 bath cottage centrally located

4.99 out of 5 average rating, 139 reviews

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.

Home in Afton

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

A sunroom is filled with natural light, featuring a dark sofa adorned with decorative pillows. A small side table with a lamp is positioned beside the couch. A comfortable chair complements the seating area, while large windows showcase lush greenery outside.

4.97 out of 5 average rating, 115 reviews

The Venable - A Gorgeous Home in the Heart of UVA

Superhost

Home in Fifeville

5 out of 5 average rating, 9 reviews

Cozy Charlottesville Loft

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.

4.83 out of 5 average rating, 203 reviews

Charming Belmont / Downtown cottage

5 out of 5 average rating, 73 reviews

A bright living room is highlighted by a high ceiling and large windows, allowing natural light to flow in. It features a cozy sofa with patterned pillows, two armchairs, and artwork adorning the walls. Potted plants add a touch of greenery to the space.

Home in Woolen Mills

The Modern at Woolen Mills

4.94 out of 5 average rating, 371 reviews

A spacious living area features exposed brick walls and large windows allowing natural light to fill the space. Two green velvet chairs and a grey sectional surround a coffee table on a colorful rug, complemented by modern artwork and a staircase leading to the upper level.

Home in North Downtown

Charlottesville Dreamin' | Parking | Sleeps 8

The exterior of a brick house is framed by vibrant autumn foliage, with golden and orange leaves. A pathway of bricks leads to the entrance, and subtle landscaping includes a small tree displaying colorful leaves, contributing to a serene outdoor setting.