Guest house holiday rentals in Charlottesville

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Top-rated guest house rentals in Charlottesville

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Guest favourite

Guest house in Orange

5 out of 5 average rating, 222 reviews

Taj Garage Guesthouse

Newly constructed (2021) above garage guesthouse with private, self check-in entrance, off-street parking, located among historic homes just 4 blocks to restaurants, shops, park and art galleries in downtown Orange. Guesthouse includes a fully equipped kitchen, queen bed, full bath, seating area, TV, wifi and balcony. Handcrafted heart pine furniture. Level 2 EV Charger. Kitchen includes refrig, stove, microwave, toaster and Keurig. Close to superb wineries, breweries and historic sites.

Guest favourite

Guest house in Charlottesville

4.98 out of 5 average rating, 133 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.

Guest favourite

Guest house in Charlottesville

4.91 out of 5 average rating, 548 reviews

Downtown studio, walk to corner/downtown mall/UVA

Professionally cleaned, intimate space, walking distance to all of C-ville then you have found the right place! Come stay with us and enjoy everything this amazing city has to offer. The house is a separate structure from the main home. It has all the amenities of a hotel room to include off street parking (at no extra cost might I add) . It is centrally located with a 5-12 min walk to the Amtrak, west main shops, Preston Ave, downtown mall, The Corner, and UVA. See "Space" for more details.

Guest favourite

Guest house in Crozet

4.97 out of 5 average rating, 148 reviews

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.

Guest favourite

Guest house in Charlottesville

4.98 out of 5 average rating, 263 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

Guest favourite

Guest house in Earlysville

4.98 out of 5 average rating, 333 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.

Guest favourite

Guest house in Troy

4.99 out of 5 average rating, 147 reviews

Beaver Pond Farm - Near Charlottesville

Relax at this unique and tranquil getaway. Sit on the screened in porch and enjoy the sights and sounds of nature while you enjoy a beverage. Take a walk on miles of trails that are adjacent to the property. Visit the Downtown Mall, Monticello, a Winery, a Brewery, or UVA (20 min). Enjoy a dip in the pool (JUN-AUG) or relax by the firepit - perhaps joined by the horses for cocktails. Feel like staying in - SmartTVs and Gig-speed Internet await. Easy checkout. No cleaning fee.

Guest favourite

Guest house in Belmont

4.99 out of 5 average rating, 110 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

Guest favourite

Guest house in Charlottesville

4.91 out of 5 average rating, 124 reviews

Cavalier Carriage House Suite | Near UVA

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.

Guest favourite

Guest house in Charlottesville

5 out of 5 average rating, 147 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.

Guest favourite

Guest house in Afton

5 out of 5 average rating, 124 reviews

WEEKENDS, WINE & WAHOOS! - Private Detached Studio

Enjoy an escape in the heart of Virginia wine country! This renovated, detached studio is only 22 mins. south of Charlottesville & UVa. Whether you're attending a wedding or exploring everything the area has to offer, it's an ideal spot. You're close to multiple vineyards, Shenandoah NP/The Blue Ridge Parkway, breweries & hiking. Plus, there's fast, reliable internet & your own deck for relaxing.

Guest favourite

Guest house in Waynesboro

4.91 out of 5 average rating, 353 reviews

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.

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for guest house rentals in Charlottesville

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly guest house rentals

Guest favourite

Guest house in Charlottesville

4.92 out of 5 average rating, 144 reviews

The Cottage at Eastwood Farm and Winery

Guest house in Louisa

4.78 out of 5 average rating, 81 reviews

Waterfront LAKE ANNA home w/ dock PUBLIC/COLD SIDE

Guest favourite

Guest house in Boston

4.98 out of 5 average rating, 167 reviews

The Bunkhouse- simple & serene w/mountain views

Guest house in Madison

4.8 out of 5 average rating, 79 reviews

Madison Farmette Guest House

Guest favourite

Guest house in Madison

4.97 out of 5 average rating, 236 reviews

Hebron Valley Cottage

Guest favourite

Guest house in Charlottesville

5 out of 5 average rating, 118 reviews

Hidden Gem near town and Monticello with a pool

Superhost

Guest house in Charlottesville

4.85 out of 5 average rating, 40 reviews

Luxury 2BR Suite One Mile From UVa, Near Downtown

Guest favourite

Guest house in Ruckersville

4.99 out of 5 average rating, 268 reviews

Mountain Guesthouse*Hot Tub*WiFi*Firepit*Grill*SNP

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Guest house rentals with a patio

Guest favourite

Guest house in Mount Crawford

4.95 out of 5 average rating, 132 reviews

Country Cabin near JMU/ Skyline Dr / Massanutten

Guest favourite

Guest house in Charlottesville

4.98 out of 5 average rating, 40 reviews

Stony Point Cottage

Guest favourite

Guest house in Barboursville

4.97 out of 5 average rating, 35 reviews

Burnley Cottage

Guest favourite

Guest house in Charlottesville

4.97 out of 5 average rating, 39 reviews

Cozy Cottage Retreat at The Midway

Guest favourite

Guest house in North Downtown

5 out of 5 average rating, 17 reviews

Belmont Hidden Gem

Guest favourite

Guest house in Waynesboro

4.9 out of 5 average rating, 62 reviews

Nona's Cottage-Waynesboro/Shenandoah Valley, VA

Superhost

Guest house in Keswick

4.86 out of 5 average rating, 35 reviews

The Woodhouse Cottage

Guest favourite

Guest house in Charlottesville

5 out of 5 average rating, 50 reviews

Historic HomeTract Cottage UVA/Charlottesville/Ivy

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Guest house rentals with a washing machine and dryer

Superhost

Guest house in Belmont

4.7 out of 5 average rating, 146 reviews

Belmont Carriage House

Guest favourite

Guest house in New Canton

5 out of 5 average rating, 7 reviews

Nordic Nights Studio & Sauna

Guest favourite

Guest house in Charlottesville

4.98 out of 5 average rating, 47 reviews

Charming one room cottage with parking.

Guest favourite

Guest house in Afton

4.92 out of 5 average rating, 542 reviews

Tiny House Bliss on Brew Ridge Trail. Wintergreen

Guest favourite

Guest house in Nellysford

4.98 out of 5 average rating, 51 reviews

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

Guest favourite

Guest house in Culpeper

4.97 out of 5 average rating, 31 reviews

The Wheelhouse at Mount Airy

Guest favourite

Guest house in Gordonsville

4.91 out of 5 average rating, 179 reviews

La Petite Maison at Hedgeapple Hollow

Guest favourite

Guest house in Cartersville

5 out of 5 average rating, 14 reviews

The Bright Spot Guest House

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Quick stats about guest house rentals in Charlottesville

Total rentals
30 properties
Total number of reviews
3.5K reviews
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi
Popular amenities
Kitchen, Wifi and Pool
Local attractions
Shenandoah National Park Trust, University of Virginia and John Paul Jones Arena

Guest house holiday rentals in Charlottesville

Top-rated guest house rentals in Charlottesville

Holiday rentals for every style

Houses

Flats

Cabins

Popular amenities for guest house rentals in Charlottesville

Family-friendly guest house rentals

Guest house in Charlottesville

Guest house in Louisa

Guest house in Boston

Guest house in Madison

Guest house in Madison

Guest house in Charlottesville

Guest house in Charlottesville

Guest house in Ruckersville

Guest house rentals with a patio

Guest house in Mount Crawford

Guest house in Charlottesville

Guest house in Barboursville

Guest house in Charlottesville

Guest house in North Downtown

Guest house in Waynesboro

Guest house in Keswick

Guest house in Charlottesville

Guest house rentals with a washing machine and dryer

Guest house in Belmont

Guest house in New Canton

Guest house in Charlottesville

Guest house in Afton

Guest house in Nellysford

Guest house in Culpeper

Guest house in Gordonsville

Guest house in Cartersville

Quick stats about guest house rentals in Charlottesville

Total rentals

Total number of reviews

Rentals with dedicated workspaces

Wifi availability

Popular amenities

Local attractions

Destinations to explore