Fitness-friendly holiday rentals in Charlottesville

The Cherry Tree, downtown estate, 8 parking spaces

Excellent downtown location & beautifully restored historic home within walking distance to the downtown mall, Main Street shops, and restaurants. Incredible attention to convenience details such as a wired conference room table, plumbed coffee machines, and a power strip next to every seat and bed. No need to compromise with small rooms or fight for bathrooms. Enjoy a bathroom to every bedroom and more than plenty of space, seating, and sleeping for 16 people. Come isolate in comfort and style.

2 bdrm/2 full bath Best Views of Blue Ridge Mtns.

Best View of the Blue Ridge Mountains! Panoramic window views from the great room, dining area and kitchen. If you want to get a closer look step out on the observation deck to see the beautiful mountains and ski slopes (seasonal). Patio furniture is on the deck to enjoy morning sunrises and evening sunsets. All new stainless steel appliances in kitchen, Freshly painted throughout. 2 bedroom 2 bath Lots of activities to do at the Wintergreen Resort all year long. Year round resort activities.

Rivanna Farm Estate North I Pickleball I Pool

This historic 42-acre country estate features four distinct residences, three of which are Airbnb rentals. The "North” offers beautiful views of the Blue Ridge Mountains and includes 4 bedrooms: 2 bedrooms with queen beds, and another with 2 twin beds on the main floor, and an additional queen bedroom upstairs. The second floor has a full kitchen, living room, & dining area. On the lower level is a yoga studio, game room, outdoor patio area w/seating, and charcoal bbq. (Charcoal not provided)

Newly Built Luxury Home 3min to UVA–Near Downtown

Our house is located near UVA with 3 min drive to UVA (10 min walk) and 4 min drive from Scott Stadium (15 min walk). The house has a lot of space for large groups and there are many thing to make your stay memorable . The house includes Automatic Espresso Machine, PS5, Netflix, HBO Max, Apple TV+, ESPN+, etc. The house also is well equipped for families with kids and babies. We have exercise equipment such as rowing machine in the basement. You will have a lot of fun with the foosball table.

Rustling Meadows Nest

Enjoy the peaceful surroundings of grassy rolling hills, magnificent hardwood forest, and riding trails for self-guided enjoyment. An inspiring children and dog friendly environment. Centrally located in the urban ring of historic Charlottesville/Albemarle County, enjoy the option of hoteling your horse at beautiful Rustling Meadows Stable with the best of comforts. 2 Bedrooms with Option of a 3rd Bedroom if desired for extra $48.00 per night. Third Bedroom has full bed w/ twin overhead.

Cozy 1BD FULL PRIVATE APT in Charlottesville, VA

This is a full private apartment located in the lower level of a house in the Greenbrier neighborhood in the heart of Charlottesville, VA. It is self contained and includes a bedroom, living room, utility room, game room with pool table, darts and ping pong, small gym, and full kitchen and bath. 5 minutes from downtown and UVA. Under 5 minutes to JPJ, Amphitheater, downtown mall and Scott Stadium. Perfect for hiking, brewery and wine tastings, weddings, vacations, graduation, etc.!

The Barn at Galleywinter Farm

Our beautiful barn built of native wood is located on a 20 acre working horse and health farm in the Rockfish Valley. One queen cedar bed and a single bed. Great for those in need of a relaxing getaway, or anyone looking for aesthetic surroundings and food for the soul. This is a REAL Barn where you feel close to nature. There is a beautiful new all- wood outhouse with a composting toilet 20' from the barn as well as an outdoor shower. Located 4 miles from Skyline Drive.

Caprica (Private Ground Level Home)

Private Whole Lower Level. Caprica is the essential stay for an unforgettable Shenandoah Valley experience! Situated with perfect views of the outside, the guest quarters space is over 2200 sq ft. and features a lounge/media center, common meeting area, bedrooms & bathrooms, entertainment center with air hockey table and ping pong, and a fully supplied gym. See pictures for more details and information. Anyone is welcome to use the balcony, back patio, and fire pit.

Private Remodeled Pool on 151 Trail

Welcome to Nelson County! Cookies Place is the perfect spot for a family vacation or an adult getaway. Private pool. Tucked in a quiet neighborhood right off the hoppin Nelson 151 Beverage Trail. Breweries, wineries, cideries, hiking trails, scenic views.. all close by. Venture out to Charlottesville, Waynesboro, Blue Ridge Parkway, Blue Ridge Tunnel or Wintergreen Ski Resort. Pool: Pool will be closed starting September 4, 2025 Photos by Jill Ferrell Photography