Guesthouse holiday rentals in Charlottesville

A bright living area features a tall ceiling with two large windows, allowing natural light to fill the space. A gray sectional sofa is accompanied by a wooden coffee table and an armchair. Artwork is displayed on the wall, enhancing the contemporary ambiance.

4.98 out of 5 average rating, 188 reviews

Delightful loft cottage in the heart of CVille

A short walk to the Downtown Mall, Main Street shops and restaurants, and the UVA hospital, this brand-new guest house will welcome you to the heart of Charlottesville. Cozy and modern, our light filled sanctuary features high end finishes and warm details. A comfortable desk and high-speed internet makes the space perfectly suited for traveling professionals. Make this your urban home base, as you explore the Virginia outdoors, with dozens of wineries and gorgeous hikes within a short drive.

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5.0 out of 5 average rating, 150 reviews

Historic HomeTract Cottage UVA/Charlottesville/Ivy

Hometract Cottage is a historic one bedroom home (NRHP, circa 1800) centrally located 15 minutes or less from Charlottesville, UVA, Crozet, Monticello, wineries and more. The cottage features ensuite bath, fully stocked kitchen, living/workspace with comfortable sleeper sofa, mature landscaping for privacy, and covered front porch. Hometract is a quiet 3-acre property with terraced garden views. Visit our chicken coop, relax in the hammock, or walk to the garden shop or Duner's restaurant.

ValueFamilyAir conditioning

4.97 out of 5 average rating, 233 reviews

A welcoming living area is highlighted by a comfortable couch, complemented by a decorative pillow. Natural light enters through windows adorned with light curtains, creating an airy feel. A stylish area rug adds warmth, while a lamp and small plant enhance the inviting atmosphere.

Guesthouse in Crozet

Crozet Cottage | Close to Wineries & DT Crozet

Enjoy a cozy getaway at our centrally-located carriage house, in the heart of sought-after Crozet, VA. Completely renovated in 2022, the carriage house feels brand new! Our space offers 1 queen bed and 1 full-bed pull-out couch. The space is .5 miles from downtown Crozet, 2.5 miles to King Family Vineyard and 3.5 miles to Chiles Orchard. It is equipped with a kitchen, a large closet (fits a pack n' play!), high speed internet and Apple TV. We have assigned parking spots in the driveway.

ValueFamilyLaundry

A modern structure is nestled among tall trees, surrounded by lush greenery. The building features a dark exterior with large windows, allowing natural light to highlight the inviting entrance. Vibrant plants and foliage are visible in the foreground, enhancing the serene landscape.

4.98 out of 5 average rating, 323 reviews

Renew @ Coniferidge.

Constructed in 2017 “ Renew” offers a peaceful, clean and simple space furnished with a comfortable modern mix style. It is situated a short distance from the main home and offers just the privacy you are looking for. This property, located outside beautiful Charlottesville Va. is an easy drive to restaurants, shopping, art, culture, wineries, history, parks and the Uva . Flat Screen Smart TV (use your logins to access your favorite sites ) NO pets - out of consideration of future guests

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Guesthouse in Earlysville

A charming cottage is nestled among mature trees and vibrant landscaping, featuring a welcoming entrance. The rustic structure is complemented by lush greenery and seasonal foliage, emphasizing a serene, natural setting.

4.97 out of 5 average rating, 393 reviews

Cottage at Frog Jump- woodland privacy at its best

Guesthouse ideal for two people. Small cottage (1 bed, 1 bath) is situated in a country setting on ten wooded acres along a large serene pond. It features a darling kitchenette with sink, fridge, microwave and toaster/convection oven. (No stove top, no oven.) You'll enjoy birdsong and views of various wildlife. A quiet, restful place to stay when you want to be near Shenandoah Nat’l Park, UVA, Charlottesville, Virginia wineries, Monticello, Montpelier, CHO, and other close-by attractions.

FamilyValueCondition

A charming brick cottage features a sloped metal roof and white-trimmed front door, framed by vibrant greenery and flowering bushes. A grassy area leads to the entrance, creating a welcoming exterior. Soft clouds drift above, adding to the serene outdoor setting.

4.89 out of 5 average rating, 170 reviews

The Cottage at Eastwood Farm and Winery

The Winery Cottage at Eastwood Farm and Winery is located on the historic Woodland estate, built and owned by Jefferson builder, John Dunkum in 1810. Our 78 Cville acres include our family’s winery with indoor (year round) and outdoor (Apr-Nov.) tasting rooms, extensive wooded trails, incredible mountain views and apple orchard. Nestled on the same ridge as Monticello, Carter's Mtn, Jefferson Vineyards, Blenheim and Trump Vineyards. Five minutes to Belmont and Downtown Mall.

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A solar-powered cottage is highlighted, featuring a sloped roof and large windows. A wooden deck extends from the entrance, where a welcoming red door is positioned. A dog rests on the deck, with greenery surrounding the home, enhancing the serene outdoor setting.

4.99 out of 5 average rating, 141 reviews

Sun Cottage in Downtown Charlottesville

Solar powered cottage with 15 foot ceiling, sleeps four, This unique place has a style all its own. Italian fold out couch and a loft. kitchen and outdoor deck. It Is 75 feet from our house. We are 1.0 mile from the Downtown Mall of Charlottesville in Historic Woolen Mills, 5 blocks from the Rivanna River and Park. Off street parking, 250 sq ft plus loft. Has lots of light. Enjoy fresh eggs from our chickens!there is so much in our area from hiking to eating to contemplating

ValueLocationGetting around

4.92 out of 5 average rating, 704 reviews

An interior view showcases a cozy living space with wooden walls and ceiling, abundant natural light from large windows, and a ceiling fan. A gray sofa is complemented by a colorful throw blanket, while a small dining area with bright chairs is positioned nearby.

Guesthouse in Afton

Your Perfect Blue Ridge Mountain Hideaway near 151

A luxury tiny home built without compromise. This six-figure, custom-built retreat features high-end finishes, premium materials, and a refined layout that feels both elevated and comfortable. Set in the Blue Ridge Mountains, it offers privacy and tranquility with easy access to scenic drives, hiking, renowned breweries, and local wineries—ideal for a relaxed weekend escape focused on slowing down, good food and drinks, and returning home refreshed.

ValueFamilySolo travel

The exterior of the guesthouse is presented, showcasing a modern structure with three large glass doors. A stone patio area is depicted, featuring two outdoor chairs and a fire pit with kindling. Soft outdoor lighting enhances the serene environment among lush greenery.

4.98 out of 5 average rating, 107 reviews

Clean, cozy guesthouse near historic downtown mall

You're sure to enjoy this recently built (completed March 2020), private guesthouse in the charming Little High neighborhood near downtown Charlottesville. Cozy yet uncluttered space, high-speed wi-fi, private patio area, and a helpful host make for a pleasant stay in a great location. We are less than a mile from the historic downtown mall, two miles from UVa, four miles from Monticello, and within 15 miles of numerous hikes, vineyards and breweries.

LocationFamilyIndoor spaces

A bright dining space is showcased, featuring a white table surrounded by wooden chairs. Natural light filters through large windows, highlighting the modern decor. A stylish pendant light hangs above the table, complemented by a decorative centerpiece of fresh flowers.

5.0 out of 5 average rating, 206 reviews

Luxury tiny house 3 min from UVA

Experience modern luxury in La Casita, a new tiny home in Charlottesville's charming Fry’s Spring neighborhood. This stylish retreat, perfect for 2-4 guests, offers a private bedroom, deluxe sleeper sofa, and fully equipped kitchen, fast reliable internet for working. Enjoy easy access to UVA, Monticello, and local wineries. Ideal for short or long stays, blending comfort with convenience in a pedestrian-friendly neighborhood.

ValueFamilySleep quality

Superhost

The exterior of a white carriage house is shown, featuring a peaked roof and two garage doors. A well-maintained gravel driveway leads up to the building, with lush green fields visible in the background. Decorative wall sconces are mounted on each side of the garage doors.

Guesthouse in Crozet

4.93 out of 5 average rating, 245 reviews

Crozet Carriage House

Beautiful Crozet Carriage House close to UVA, vineyards, breweries and all Charlottesville has to offer. A brand new space above a detached 2 car garage with a private entrance. It is well appointed and set in a peaceful setting. It features 1 bedroom, a living room, 1 bathroom and a refrigerator and table in the living room. Come get away in Crozet!

LocationFamilyView

4.97 out of 5 average rating, 155 reviews

A charming cottage is nestled among lush trees, featuring a porch with seating. A gravel path leads to the front of the house, surrounded by greenery. The roof is metal, and natural light illuminates the inviting exterior.

Guesthouse in Faber

Country Cottage

Take a break and unwind at this peaceful cottage tucked in the woods but close to breweries, winerys, and Charlottesville. Our property is wooded and private. Please take note that we have a dog. While pets are not allowed in the cottage our dog Posie lives here and is very friendly. The cottage is 400 sq feet of open living space.

ValueFamilyIndoor spaces

Popular amenities for Charlottesville guesthouses

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-Friendly guesthouses

4.88 out of 5 average rating, 720 reviews

A small, rustic cabin is set amidst a lush green landscape, framed by trees. The cabin features a front porch with a green door and a chimney, surrounded by a well-maintained grassy area. Natural light filters through the foliage, creating a serene atmosphere.

Guesthouse in Syria

Cozy 1 room cabin in the mountains.

ValueLocationView

4.92 out of 5 average rating, 486 reviews

A wooden sign painted in soft colors displays the name 'The Stable' in a flowing, artistic script. The background is a light gray with hints of gold, while the lettering features a warm rust tone, prominently positioned against a red door.

Guesthouse in Waynesboro

The Stable

LocationFamilyGetting around

4.96 out of 5 average rating, 129 reviews

A colorful bedroom features a queen bed and a twin bed, both with patterned bedding. Walls are adorned with framed art, and windows are dressed with blue curtains. Warm lighting is provided by bedside lamps, creating a welcoming ambiance.

Guesthouse in Faber

Acorn Inn Cottage

LocationFamilyView

4.98 out of 5 average rating, 218 reviews

Pop's Cottage

FamilyLocationAmenities

4.98 out of 5 average rating, 223 reviews

A charming, two-story structure with a green metal roof is visible. The building features classic design elements and a gravel driveway, where a dark car is parked. Lush greenery surrounds the property, with distant mountains hinting at the natural landscape.

Guesthouse in Elkton

Carriage House private, 10 min to Shen. Nat'l Park

FamilyLocationDecor

4.92 out of 5 average rating, 411 reviews

Guesthouse in Schuyler

Homestead at HeartRock

ValueLocationWalkability

4.97 out of 5 average rating, 290 reviews

The cabin exterior is illuminated at night, featuring a mounted skull above the entrance. Colorful lights cast a glow on surrounding trees, creating an enchanting atmosphere. The sleek design includes a covered porch with modern railing, highlighting the cabin's rustic charm.

Guesthouse in Troy

Cabin in The Pines

ValueFamilyLayout

4.95 out of 5 average rating, 441 reviews

A charming cottage is framed by lush greenery, with a covered porch extending across the front. Colorful flowering bushes add vibrancy to the landscape, which features well-maintained garden beds and a birdbath. The cottage is situated on a grassy area that leads to a secluded wooded backdrop.

Guesthouse in Syria

Little House on Strother Run

ValueLocationBathroom

Guesthouses with a patio

The modern kitchen features sleek white cabinetry and stainless steel appliances, including a refrigerator and stove. A large window allows natural light to fill the space. A dining table and chairs are positioned nearby, creating an inviting area for meals.

4.99 out of 5 average rating, 116 reviews

Tucked Away in Central C-ville.

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Guesthouse in Sperryville

The guest house is framed by lush greenery and softly illuminated by hanging lights that create a welcoming ambiance. A spacious porch with potted plants invites relaxation, while the multi-gabled roof and cupola add character to the charming exterior. Gravel pathways lead to the entrance.

4.99 out of 5 average rating, 150 reviews

Countryside getaway 5 min. from Old Rag parking!

LocationFamilyView

5.0 out of 5 average rating, 318 reviews

A newly constructed guesthouse features a charming exterior with a sloped red roof and white trim. A covered balcony with a red umbrella overlooks landscaped gardens. Stone pathways and greenery surround the home, enhancing the inviting outdoor space.

Guesthouse in Orange

Taj Garage Guesthouse

LocationValueQuiet

Guesthouse in Massies Mill

Lush green grass stretches across the foreground, leading to a scenic vista dominated by rolling hills and misty mountains. The trees display varying shades of green, indicating the freshness of spring, with a backdrop of soft clouds partially covering the peaks.

4.99 out of 5 average rating, 114 reviews

Solar-powered Guesthouse at Peak Time Property

FamilyLocationHeating

Guesthouse in Mount Crawford

A welcoming living area features a large area rug with floral patterns. Two couches provide comfortable seating, and a flat-screen TV is mounted on the wall. The open layout allows views into the kitchen and dining space, enhancing the connection between areas.

4.96 out of 5 average rating, 195 reviews

Country Cabin near JMU/ Skyline Dr / Massanutten

LocationFamilyIndoor spaces

4.98 out of 5 average rating, 261 reviews

The exterior of the cottage is shown, featuring a private patio area with a small round table and four chairs. A large blue and white striped umbrella provides shade. To the side, a grill is visible, and a parking area is located nearby.

Guesthouse in Reva

Adorable cottage with partial blue ridge views

FamilyLocationKitchen

4.91 out of 5 average rating, 213 reviews

Guesthouse in Shenandoah

Guesthouse with Massage Chair & GAME ROOM

LocationFamilyParks

4.99 out of 5 average rating, 100 reviews

The exterior of a rustic cottage is highlighted at night, featuring a welcoming entrance illuminated by soft lighting. A pathway leads to the door, surrounded by well-maintained lawn and trees. Windows offer glimpses of the interior, contributing to the cozy ambiance.

Guesthouse in Culpeper

The Wheelhouse at Mount Airy

LocationFamilyKitchen

Guest house rentals with a washing machine and dryer

4.87 out of 5 average rating, 346 reviews

A well-lit kitchen area features a blend of modern and rustic elements, including a farmhouse-style island with seating. Light streams through the double French doors, leading to a small dining space with two chairs and a circular rug on the floor.

Guesthouse in Crozet

Stylish Carriage House Suite near Crozet center

FamilyLocationView

4.98 out of 5 average rating, 302 reviews

An open living and dining area is displayed, featuring a wooden dining table set with decorative placemats. A comfortable seating arrangement is visible in the background, alongside a console table and artwork on the walls. Natural light enters through sliding glass doors.

Guesthouse in Afton

Mountain Cottage, Swimming Pool, Views, Nelson 151

FamilyLocationSleep quality

Guesthouse in Gordonsville

The exterior of La Petite Maison showcases a charming guest house with a large screened porch, surrounded by vibrant flower beds. A turquoise umbrella shades a lounge chair next to the seasonal in-ground pool, providing a relaxing outdoor space.

4.9 out of 5 average rating, 195 reviews

La Petite Maison at Hedgeapple Hollow

FamilyValueKitchen

4.97 out of 5 average rating, 267 reviews

A covered porch area is visible, featuring several outdoor chairs and a table. The porch is bordered by a gravel path and landscaped with stones and flowers. The expansive grassy field extends beyond the structure under a clear blue sky.

Guesthouse in Madison

Hebron Valley Cottage

LocationFamilyLaundry

Guesthouse in Harrisonburg

An open living area features rustic wooden beams and skylights, providing natural light. A comfortable sofa and armchair in soft hues are positioned near a circular table. The decor includes a framed painting and a small round table, all atop a patterned area rug.

4.96 out of 5 average rating, 175 reviews

Hideaway Studio on Ashtree Lane

FamilyLocationLayout

4.9 out of 5 average rating, 101 reviews

An aerial view captures the South Fork Shenandoah River winding through a vast landscape of open fields and wooded areas. Rolling mountains rise in the distance, providing a scenic backdrop to the tranquil setting of the countryside.

Guesthouse in Stanley

Shenandoah River Retreat

ValueFamilyQuiet

Guesthouse in Gordonsville

A charming white house is framed by a vibrant tree with red foliage, set against a clear blue sky. A gravel path leads toward the home, which features a black roof and a welcoming front porch, surrounded by well-maintained grass and shrubs.

5.0 out of 5 average rating, 48 reviews

Guest House at Annandale

FamilyLocationCheck-in

A cozy living area features a light-colored sofa adorned with decorative pillows and a wooden coffee table. Local art pieces decorate the walls, complemented by a small dining table set for two. Natural light enters through a window, brightening the space.