Guesthouse vacation rentals in Charlottesville

Stylish Carriage House Suite near Crozet center

Peaceful retreat walkable to downtown Crozet (cafes, galleries, restaurants, yoga, spa.) One bedrm, now with Queen, clawfoot tub, stovetop, granite countertops, reclaimed barn wood features, visual electric "fireplace" focal point, 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.) We give winery tours thru CrozetTrolley. Main house next door for large groups

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

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)

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.

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.

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

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. 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 a Great Pyrenees for cocktails. Feel like staying in - SmartTVs with YouTubeTV (which includes local channels) and Gig-speed Internet await. Easy checkout. No cleaning fee.

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.

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.

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.

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.

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.