Guesthouse holiday rentals in Charlottesville

4.98 out of 5 average rating, 218 reviews

Pop's Cottage

Perched on a hilltop overlooking mountains, a river and cattle , POP'S COTTAGE is a fully appointed, dog friendly , one bedroom guest cottage offering a location second to none in the heart of central Virginia's wine, brewery, bourbon and cider country. Pop's Cottage is 10 miles from UVA & within 3 miles from Pippin Hill Vineyard. Wine Enthusiast named Virginia as one of the "Top 10 Best Wine Travel Destinations" in the world, so make your reservation at Pop's Cottage! Facebook & Instagram

FamilyLocationOutdoor spaces

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

Wake to gorgeous Mountain views & rolling green meadows bordering the Rockfish River on our family estate. Private attached unit with built in pool (mid April-mid Sept)in the Blue Ridge mountains of Nelson County Virginia on the center of the 151 Brew Ridge Trail. Much preparation has gone into making your stay beautiful, convenient and comfy. No need to physically interact if that’s your desire. Enjoy swimming, hiking, kayaking, horse back riding, skiing, snowboarding, and more! 3 nite minimum

LocationFamilyKitchen

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, 186 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.

ValueFamilyIndoor spaces

5 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.

LocationValueAmenities

4.97 out of 5 average rating, 228 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.

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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, 322 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

FamilyValueQuiet

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, 390 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.

FamilyLocationBathroom

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

ValueLocationPets

4.92 out of 5 average rating, 700 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.

LocationValueView

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, 205 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.

ValueFamilyBreakfast

4.92 out of 5 average rating, 484 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

Our guesthouse is located in the historic Tree Streets Neighborhood of Waynesboro, VA, an official Appalachian Trail town, located at the southern end of the Shenandoah National Park. We've aptly named the guesthouse "The Stable" because it was originally built and functioned as a stable. It has since been converted into a cozy cottage for guests.

LocationValueParking

4.96 out of 5 average rating, 139 reviews

The cottage is set in a wooded area, elevated on a wraparound deck surrounded by mature trees. Natural light is filtered through the leaves, creating dappled patterns on the ground. The exterior features a muted color palette complemented by a charming brick chimney.

Guesthouse in Keswick

Gladstone Cottage

Charming, private 1 bedroom cottage oasis in the heart of Keswick horse country, estates and vineyards, yet only 18 minutes to UVA. Very secluded and peaceful setting. Nestled in woods but full of light. Large bay window looks out on a walk-through perennial garden. From the deck, enjoy watching horses graze in the adjacent pasture.

FamilyLocationIndoor spaces

Popular amenities for Charlottesville guesthouses

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-Friendly guesthouses

4.96 out of 5 average rating, 784 reviews

A charming guest house is nestled among lush green trees, showcasing a steeply pitched roof and large windows. A wooden staircase leads up to the entrance, which features a small deck surrounded by vibrant foliage.

Guesthouse in Hinton

StreamSide Guesthouse in Mountains/National Forest

LocationFamilyBiking

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

LocationFamilySleep quality

4.97 out of 5 average rating, 238 reviews

A modern studio space features large windows that allow natural light to fill the room. A cozy yellow chair sits beside a small coffee table, with a guitar resting on a stand nearby. The bed area is visible in the background, framed by a stylish shelf.

Guesthouse in Boston

The Skyhouse- simple & serene w/mountain views

FamilyValueComfort

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

FamilyLocationBackyard

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, 131 reviews

Honey House-beautiful loft 9 minutes from UVA

LocationFamilyDecor

4.97 out of 5 average rating, 288 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

LocationFamilyWalkability

4.92 out of 5 average rating, 411 reviews

Guesthouse in Schuyler

Homestead at HeartRock

LocationValueParking

4.88 out of 5 average rating, 718 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.

FamilyLocationCleanliness

Guesthouses with a patio

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.

4.95 out of 5 average rating, 125 reviews

Swanky and Modern Downtown Guesthouse

FamilyLocationOutdoor spaces

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, 112 reviews

Solar-powered Guesthouse at Peak Time Property

LocationFamilyCleanliness

The kitchen is equipped with modern appliances, including a stainless-steel refrigerator, range oven, and dishwasher. A wooden countertop has bar seating for two, while natural light illuminates the space. Neutral green walls add a calming touch, complemented by sleek lighting fixtures.

4.92 out of 5 average rating, 38 reviews

Eastham Guesthouse

FamilyLocationAmenities

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, 194 reviews

Country Cabin near JMU/ Skyline Dr / Massanutten

ValueLocationIndoor spaces

4.9 out of 5 average rating, 210 reviews

Guesthouse in Shenandoah

Guesthouse with Massage Chair & GAME ROOM

FamilyLocationQuiet

4.91 out of 5 average rating, 102 reviews

A spacious bedroom features a king-sized bed with a dark blanket. Warm wood accents and a vintage wardrobe enhance the decor. Soft lighting from a decorative chandelier complements the green walls. The room's windows are adorned with patterned shades, and artwork is displayed on the walls.

Guesthouse in Culpeper

Charming, Private 1 Bedroom Suite in Downtown

FamilyLocationView

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.

4.96 out of 5 average rating, 80 reviews

Belmont Hidden Gem

LocationBackyardAir conditioning

5 out of 5 average rating, 317 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

LocationFamilyLaundry

Guest house rentals with a washing machine and dryer

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.

5 out of 5 average rating, 49 reviews

Greenbrier Guesthouse: a Charlottesville gem!

FamilyLocationSleep quality

4.99 out of 5 average rating, 83 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

FamilyValueHiking

4.97 out of 5 average rating, 64 reviews

Charming one room cottage with parking.

FamilyLocationQuiet

4.87 out of 5 average rating, 344 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

FamilyValueCheck-in

4.99 out of 5 average rating, 85 reviews

A modern garage apartment stands amidst lush greenery, showcasing a dark exterior with wooden accents. A gravel driveway leads to the entrance, where steps ascend to the private apartment above. Large garage doors and a small plant add subtle details to the setting.

Guesthouse in Nellysford

The Nest...lovely 2 bedroom apartment in the woods

LocationFamilyNearby

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, 48 reviews

Guest House at Annandale

LocationFamilyAmenities

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.

4.98 out of 5 average rating, 93 reviews

Burnley Cottage

FamilyValueBiking