Family-friendly holiday rentals in Charlottesville

Idyllic Cottage Retreat

⭐️ Condé Nast Traveler Approved ⭐️ Cozy cottage nestled on a historic 400-acre Blue Ridge Mountain farm abutting Shenandoah National Park. Every space inside this cozy cottage is creatively styled, with tons of perfectly imperfect charm. Outside, a hammock beneath the elm trees, fire pit and grill, all allow for enjoying the splendor of this peaceful enclave. Excellent day-tripping to many of central Virginia's celebrated wineries and breweries, as well as scenic drives and hiking trails.

Green Willow Farm apartment near Monticello

*Winter update: Jan/mid-March. Our fairly long flat gravel driveway is hard to navigate in snow. AWD, or heavier cars, are helpful. We will shovel some, allow sun to melt the remaining. FYI when booking. Spacious farm apartment(walkout apt below our living space) in the rolling hills of Virginia. Galley kitchen. Large fireplace. Private entrance. Stone patio. Close to downtown Charlottesville and UVA(+/- 8 miles). A few miles from Monticello, Many vineyards, and Carter's Mountain Orchard.

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.

The LoriAnn, A Boutique Stay New Sleep Number Bed

This beautifully restored 1940’s home in the City of Waynesboro is just a short drive from the Blue Ridge Parkway. Modern amenities, light complimentary breakfast items and assurance of comfort awaits! Enjoy one of a kind Autographed Movie and TV Memorabilia. The spacious front porch is yours to enjoy including a 100 yr old porch swing that belonged to my Great Grandmother. Along with the Parkway & Skyline Drive, enjoy Restaurants, Breweries, Vineyards, movie theaters and exploring Route 151.

The Brothers Great Room

Your private guest suite is located in Northern Albemarle County Virginia. We cannot allow cats(due to family members with allergies and the extra cleaning required) We are just off of Route 29 with easy access to local venues. The suite is up one flight of stairs. Albemarle County is central to the University of Virginia, Monticello, Montpelier, wineries, craft beer breweries, and wedding venues in the area. Your dogs may run the open areas. Please clean up after your pet.

Moonfire Farm cozy Shenandoah Region Getaway

Experience charm and nature at Moonfire Farm! Our finished basement on a 5-acre hobby farm offers delightful animal encounters with chickens, ducks, alpacas, and hilarious goats. Our active family of three, including our 7-year-old daughter Piper, welcomes you. High-speed Internet and nearby wineries, breweries, hiking trails, and pick-your-own fruit locations await you. Explore our guidebook for recommendations. Book now for a memorable farm getaway!

Guesthouse at Hamilton Oaks

Escape to our guesthouse on a little farmette. This peaceful setting tucked away on several acres along a creek with nature trails is the perfect mountain getaway. We are conveniently situated near quaint wineries, breweries along with hiking and the Blue Ridge Parkway that is a short hop, jump and a skip away. Every effort has been made to keep this a green haven, chemical and synthetic scent free, so you can leave recharged and rested. Non-smoking

The Loft at Minor Mill - Private loft apartment.

Our place is a newly constructed barn loft in our 1960's barn. Enjoy beautiful views of the surrounding countryside from large windows and a private balcony. The barn is surrounded by our horse pastures and neighboring fields. Self check in with the key lockbox. This loft is separate from the main house where we live. Private parking and entrance for our guests directly outside of barn loft (this is separate from the main house driveway).

Oxford Cottage: Cville’s favorite tiny home!

Tiny living done right! Discover 350 sq ft of stylish simplicity in this thoughtfully designed mini cottage. With an airy entry, cozy living area, smart kitchenette, full bath, lofted sleeping nook, and clever storage, it’s perfect for 1–4 guests seeking a relaxed stay—whether for a romantic retreat, work escape, quick stopover, or lively Charlottesville event like weddings, concerts, or triathlons.

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.

Beautiful, Cozy, Downtown Apt!

Enjoy a stylish experience at this centrally-located place. Beautifully curated apartment with luxury kitchen, tiled bathroom and wonderful deck. It has two split units to keep the place as cool or as warm as you desire. Semi-firm Queen mattress for a perfect nights sleep. A short walk to the Historic Downtown Malls shops and restaurants and The Rivanna River for tubing, swimming, biking, picnics.

2 King/1 Twin Close to Downtown & UVA

⭐️Two bedroom lower-level apartment (2 king beds, 1 twin XL, 1 toddler bed, 1 pack-n-play) in a quiet neighborhood near downtown! ⭐️Our guests rave about the excellent value, amenities, & cleanliness! 📍1 mile from UVA Hospital and Downtown Mall 📍1.6 miles from UVA ⭐️No smoking! ⭐️Please read note about the slope to the entrance 🟢The person booking must be present during the stay.