Guesthouse holiday 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-beautiful loft 9 minutes from UVA

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)

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.

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

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

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.

Luxury tiny house 3 min from UVA

La Casita, a new tiny home, combines modern luxury with a prime location near UVA, wineries, and Monticello. Designed to offer custom furnishings and luxurious touches, La Casita is situated in the residential, pedestrian-friendly neighborhood of Fry’s Spring, conveniently located near I-64. Residents can enjoy easy access to restaurants and Scott Stadium. Amenities include high-speed internet and other modern conveniences.

Walk Downtown and to UVA

🏳️‍🌈 ALL ARE WELCOME 🏳️‍🌈 Please note: the Pool House is for 1-2 adult guests only. The pool is for guests only and is a shared space with the owners and their family. Great space in a great location- close to everything! Neighborhood restaurants, coffee shops, and breweries. Only 1/2 mile to the Downtown mall, UVA, and Main Street. Private space with a kitchen, full bath, and queen bed.

Cabin in The Pines

The natural wood cabin is conveniently located 12 miles east of Charlottesville on a private 100 acre farm. The owners are on property which is located near Interstate 64, a major shopping center, Martha Jefferson Hospital, University of Virginia as well as many vineyards, breweries, and historic attractions.