Guesthouse vacation rentals in Charlottesville

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Top-rated guesthouse rentals in Charlottesville

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Guest favorite

Guesthouse in Charlottesville

5 out of 5 average rating, 105 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)

Guest favorite

Guesthouse in Orange

5 out of 5 average rating, 228 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 favorite

Guesthouse in Charlottesville

4.98 out of 5 average rating, 136 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 favorite

Guesthouse in Charlottesville

4.91 out of 5 average rating, 554 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 favorite

Guesthouse in Crozet

4.97 out of 5 average rating, 155 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 favorite

Guesthouse in Charlottesville

4.98 out of 5 average rating, 267 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 favorite

Guesthouse in Earlysville

4.98 out of 5 average rating, 336 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 favorite

Guesthouse in Troy

4.99 out of 5 average rating, 155 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 favorite

Guesthouse in Belmont

4.99 out of 5 average rating, 113 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 favorite

Guesthouse in Crozet

4.86 out of 5 average rating, 296 reviews

Stylish Carriage House Suite near Crozet center

Peaceful retreat walkable to downtown Crozet (coffee shops, galleries, restaurants, yoga.) One bedrm, large bathrm with clawfoot tub, stovetop kitchen with granite countertops, electric fireplace, reclaimed barn wood features, and private deck. (Access to main house yard w permission, each time.) One small non-shed dog on Nexgard with permission and fee. (Some other breeds with discussion and sweep on check-out.) Find us for winery tours at CrozetTrolley.

Guest favorite

Guesthouse in Charlottesville

4.95 out of 5 average rating, 284 reviews

Walk to UVa from our Charming Tiny Home

Walk to UVa from this brand-new 250sq ft "tiny home". Its perfect for game days (1 mile walk along sidewalks to Scott Stadium) or a stylish alternative to hotels for events or work travel! This cottage features a open floor plan with vaulted ceiling, a living room with TV/WiFi, kitchenette, bathroom with tub/shower and sleeping loft. Accommodates 1-4 people looking for a modern, comfortable and centrally-located place to stay.

Guest favorite

Guesthouse in Charlottesville

5 out of 5 average rating, 150 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.