Guesthouse holiday rentals in Charlottesville

A light-filled living area features large windows that overlook a serene outdoor space. A cozy sofa with cushions is positioned beside a standing lamp, while a decorative rug lies on the polished wooden floor. A potted plant adds a touch of greenery to the inviting atmosphere.

5 out of 5 average rating, 120 reviews

Honey House-modern loft near UVA/Monticello

Modern loft style 800sqft guesthouse. Lots of light and privacy in a quiet neighborhood, just 7-10 minutes to Scott Stadium/UVA/restaurants/downtown mall and Thomas Jefferson’s Monticello. Central to many wineries/breweries. You are in nature but close to everything Charlottesville. With a comfortable Queen size bed, and sleeping cot available if necessary. It is clean, comfortable and spacious. A great place to unwind for a good night’s sleep and sweet dreams. (discount apply to weekly/monthly)

4.92 out of 5 average rating, 615 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

Spacious Tiny Home Close to Wine, Beer & Mountains

A six-figure tiny home in the epicenter of VA's Brew Ridge Trail. FORBES listed this model as the most beautiful tiny house in the world. "Big Tiny", built in 2017, is a luxurious retreat that is huge on both character and amenities. This handcrafted home boasts a full-sized kitchen private bedroom, cozy sleeping loft, 2 large screen TVs, and full bath with tub. With a cathedral ceiling and walls of windows, this Escape Traveler XL is the flagship offering of the premiere tiny home builder.

4.98 out of 5 average rating, 161 reviews

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.

Guesthouse in Fifeville

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.

5 out of 5 average rating, 282 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

Above garage guesthouse with private, self check-in entrance, off-street parking, among historic homes, 4 blocks to restaurants, shops, park, etc. in downtown Orange. Includes a fully equipped kitchen, queen bed, full bath, seating area, TV, wifi and balcony. Custom heart pine furniture, EV charger, refrig, stove, microwave, toaster and Keurig. Close to superb wineries, breweries and historic sites. Four blocks from the railroad so you will occasionally hear "that lonesome whistle blow".

A covered front porch features a mix of seating options, including wicker chairs and a small table. Hanging planters add greenery, while potted plants contribute to the inviting setting. The porch overlooks mature landscaping, providing a serene outdoor environment.

5 out of 5 average rating, 102 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.

4.97 out of 5 average rating, 199 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.

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, 300 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

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.

4.98 out of 5 average rating, 377 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.

Guesthouse in Earlysville

An open studio space features vaulted ceilings with decorative wooden beams. Soft lighting from large paper lanterns illuminates the room, adorned with large plants and a seating area that includes a cozy couch and mixed seating. Large windows allow ample natural light and outdoor views.

4.95 out of 5 average rating, 193 reviews

Modern Cottage near Charlottesville

Bright and open studio space that sits on a 2.5 acre parcel and is about 150 feet away from the main house where we live. It is less than 10 minutes to the airport and under 30 minutes to downtown. The space features a kitchenette, one full bath and an open lofted bedroom space (queen size bed) upstairs. The twin beds are located on the main floor. We can only allow a maximum of 2 cars due to limited space on the property. Use of candles or fire stove is not permitted.

Guesthouse in Fry's Spring

A well-appointed sleeping area features a dual-purpose bed with a dark blue coverlet and neatly arranged towels. A large window allows natural light to illuminate the space, complemented by a chair and colorful area rug that adds warmth to the wood floors.

4.88 out of 5 average rating, 162 reviews

Cavalier Suite | Near UVA | Amenities | Parking

Small yet mighty. This carriage house is the perfect retreat for UVA games, special events, and those exploring Charlottesville. Conveniently located within walking distance to Scott Stadium, and a short distance to UVA, Downtown Charlottesville, and 5th Street Station Shopping Center. Hosts have 2 small, friendly dogs (Mac and Pippie) in the main house which may be seen in the patio entrance area. Guests have access to patio and grill.

4.87 out of 5 average rating, 682 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.

In the heart of the Shenandoah mountains. 1 mile from White Oak Canyon and Old Rag for amazing hikes. Perfect for the fly fisherman (lots of local streams) or a nice quiet get-away for a couple. Once you park your car you can sit back and just listen to the river flowing in the back yard & enjoy a nice beverage next to the fire pit. The property is a very special place! UPDATE: New kitchen counters and new table and chairs

Guesthouse in Fry's Spring

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 out of 5 average rating, 184 reviews

Luxury tiny house 3 min from UVA

La Casita is a new tiny home combining modern luxury with central location adjacent to UVA, central to wineries, and 10 minutes from Monticello. La Casita is design built to offer custom furnishings and luxurious touches. We are in the residential pedestrian-friendly neighborhood of Fry's Spring, near I 64. Walk to restaurants and Scott Stadium. Enjoy all amenities including a high-speed internet.

Popular amenities for Charlottesville guesthouses

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-Friendly guesthouses

4.71 out of 5 average rating, 155 reviews

The exterior of the Carriage House features a modern design with white siding and black shutters. A welcoming front door is adorned with a decorative wreath. Solar panels are positioned on the roof, and a landscaped garden with plants and mulch runs alongside the stone pathway.

Guesthouse in Belmont

Belmont Carriage House

Guesthouse in Woolen Mills

4.97 out of 5 average rating, 59 reviews

Charming one room cottage with parking.

Guesthouse in Harrisonburg

The studio apartment features a spacious bed with white bedding, complemented by a brown leather futon. A flat screen TV is mounted on the wall opposite the bed. A modern kitchenette with dark cabinetry and light countertops is visible, along with polished wooden flooring.

4.94 out of 5 average rating, 98 reviews

Swanky and Modern Downtown Guesthouse

4.95 out of 5 average rating, 20 reviews

The studio apartment features hardwood flooring, with a spacious arrangement including a king bed, a cozy sofa, and a dining table. Natural light enters through large windows, and a ceiling fan adds functionality to the serene space.

Guesthouse in Troy

Memas Place Close to multiple Vineyards

5 out of 5 average rating, 45 reviews

A hot tub is positioned on a wooden deck, providing an unobstructed view of rolling hills and trees. The sky displays soft pastel colors during sunset, enhancing the serene atmosphere of the surrounding countryside.

Guesthouse in Culpeper

Rare Mountain Views in Culpeper ~ Hot tub ~ Arcade

4.98 out of 5 average rating, 59 reviews

A welcoming kitchen space is displayed with vibrant yellow walls. Stainless steel appliances include a refrigerator and an oven with a hood. A wooden dining table is set with placemats, and natural light filters through the window above the sink.

Guesthouse in Staunton

Peaceful rural retreat with pool and spa

5 out of 5 average rating, 87 reviews

The cottage features a two-story structure with a white exterior and black accents. A private deck is visible on the second floor, providing outdoor space. The surrounding lawn is lush, offering a serene setting with glimpses of the pasture and trees in the background.

Guesthouse in Arrington

Crestvue Cottage

A spacious living area features a light-colored sofa and a wooden coffee table. Bright lighting illuminates the room, which opens to a modern kitchen with bar seating. A large mirror with a colorful frame enhances the sense of space, while plush carpet adds comfort.

4.84 out of 5 average rating, 49 reviews

Luxury 2BR Suite One Mile From UVa, Near Downtown

Guesthouses with a patio

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, 91 reviews

Solar-powered Guesthouse at Peak Time Property

A broad view of lush green fields extends under a bright blue sky dotted with soft white clouds. The surrounding landscape showcases the gentle slopes of the Blue Ridge mountains, framed by a variety of trees and greenery, offering a serene outdoor setting.

5 out of 5 average rating, 17 reviews

Spacious carriage house on 1780’s farm

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, 168 reviews

Country Cabin near JMU/ Skyline Dr / Massanutten

4.99 out of 5 average rating, 199 reviews

An aerial view captures a spacious guest house nestled among trees displaying vibrant autumn foliage. The surrounding landscape features a mix of green and colorful leaves, with an open area visible beside the property. Outdoor amenities are discernible, blending harmoniously with the natural setting.

Guesthouse in Troy

Beaver Pond Farm - Near Charlottesville

4.93 out of 5 average rating, 136 reviews

Guesthouse in Shenandoah

Guesthouse with Massage Chair & GAME ROOM

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 out of 5 average rating, 37 reviews

Guest House at Annandale

Guesthouse in Barboursville

An open kitchen features a spacious wooden island with black bar stools. Modern appliances are visible, along with open shelving displaying kitchenware. Light grey walls provide a neutral backdrop, while a doorway leads to adjacent areas, enhancing the layout's flow.

4.97 out of 5 average rating, 74 reviews

Burnley Cottage

The cottage is set against a backdrop of rolling hills under a serene sky. A porch is visible in the front, flanked by trees, and the landscape features a spacious lawn. A small shed stands in the background, completing the secluded countryside ambiance.

4.98 out of 5 average rating, 57 reviews

Cozy Cottage Retreat at The Midway

Guest house rentals with a washing machine and dryer

5 out of 5 average rating, 30 reviews

The kitchenette features a modern design with a light wood cabinetry and patterned wall. Appliances include an electric range, microwave, and refrigerator. A washer and dryer are conveniently positioned beside the kitchen area. Natural light enters through a window, illuminating the space.

Guesthouse in Greenbrier

Greenbrier Guesthouse: a Charlottesville gem!

5 out of 5 average rating, 58 reviews

A charming two-story loft studio features a red exterior with a modern design and a covered carport. A set of stairs leads to the entrance, while lush greenery and well-maintained landscaping surround the building, creating an inviting outdoor space.

Guesthouse in Crozet

The Loft at St. George

4.86 out of 5 average rating, 323 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

Guesthouse in 10th and Page

The interior space showcases a sliding barn-style door leading to the bathroom, with a view of the kitchenette area featuring wooden cabinetry and stainless steel appliances. Natural light enters through the nearby glass door, enhancing the warm color palette of the room.

4.89 out of 5 average rating, 630 reviews

Downtown studio, walk to corner/downtown mall/UVA

Guesthouse in North Downtown

A pebbled pathway is flanked by lush greenery and planters, leading the eye towards a large tree. A small metal table and chairs invite outdoor seating, nestled among the tranquil surroundings of the cottage.

4.77 out of 5 average rating, 125 reviews

Historic Cottage in Downtown Charlottesville

4.97 out of 5 average rating, 256 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

5 out of 5 average rating, 63 reviews

A cozy outdoor patio is illuminated by soft string lights, featuring two comfortable chairs positioned near a fire pit. The cottage exterior, adorned with warm lighting, invites relaxation in a serene evening setting, with lush green grass surrounding the space.

Guesthouse in Culpeper

The Winehouse at Mount Airy