Family-friendly holiday rentals in Charlottesville

The Peony Cottage in Charlottesville

This private cottage is conveniently located between Crozet and Ivy. Perfect location for accessing Monticello Wine Trail, the Blue Ridge Parkway/Skyline Drive, Wintergreen Resort, and enjoying all University of Virginia events! 3 miles from Downtown Crozet & King Family Vineyard 4.5 miles from Chiles Orchard 8.5 miles from John Paul Jones Arena 10 miles from Blue Ridge Parkway - North Entrance 30 miles from Wintergreen Resort Join us as we watch the progress of our newly planted peony field!

Historic cottage with stunning mountain views

Welcome to Rose Cottage in picturesque Albemarle County, where you'll enjoy expansive 360-degree views of the mountains surrounding historic Cove Lawn Farm. Relax in the tranquil rural setting or stroll more than two miles of comfortable walking paths that wind through 25 acres of stream-lined hayfields. From Rose Cottage, you're just minutes from the best local cideries, distilleries, and wineries including Pippin Hill Farm & Vineyards. Easy 20-minute drive to UVa and 22 minutes to Monticello.

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.

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.

Mountain Overlook House - Blue Ridge Parkway

Unique octagonal house with stunning views of the Blue Ridge Mountains of Virginia. Located 2 miles from I-64, 15 minutes to downtown Waynesboro and an easy 25 min drive to Charlottesville and UVA. Open floor plan, perfect for gathering, and long-range 180 degree views from nearly every room. Fully equipped renovated kitchen. Quality linens and bedding. Rustic, yet modern decor. Home features large fireplace, outside fire pit, wifi, and board games galore. Stargazing and birdwatching heaven.

Afton, Mountain View Mini Farm

Welcome to Mountain View Mini Farm! We are located in the Rockfish Valley(Afton, VA)with amazing views of the Blue Ridge Mountains. Our farm is just minutes to wineries, breweries, cideries, Shenandoah National Park and more! There is so much to do close by, but once you get on the farm, you won't want to leave! We have a total of 5 horses, with 3 being mini rescue horses. There's a fire pit area where you can roast S'mores while you watch the sunset. Be sure to look at bedrm 2 description.

Lux Country Retreat minutes from Charlottesville!

Located just off route 29 this private luxury retreat with surrounding 2 acre fenced yard is one mile from Pippin Hill Farm & Vineyard and only 15 minutes from UVA/Charlottesville. You will find this home spacious, bright and airy, perfect for entertaining groups or families. The house is completely equipped with everything you may need to host the perfect getaway! Nearby attractions: Pippin Hill, Albemarle Ciderworks, Ragged Branch Distillery, Potter's Craft Cider and Charlottesville!

Shenandoah Stargazer with Sauna

Stargazer is the perfect place to get away from it all! The stillness and serenity of being nestled in a bird and wildlife sanctuary is so good for your soul. Watch the sunrise from a hanging basket chair at 2700 feet of elevation, or wait for moonrise and toast spectacular star views! Relax in the sauna after a day filled with hiking and an al fresco meal on the deck. Roast s’mores at the deck fire table or over the side yard fire pit. There's magic in the air at this mountaintop retreat!

Adorable cottage steps from Grounds

A cozy Milton Grigg designed cottage and detached carriage house three minutes walk to the Lawn and ten minutes walk to the Stadium. Nestled in a wooded neighborhood. Perfect for visiting parents, UVA chapel weddings, med student rotations, and football games. NOTE: The cottage sleeps five adults and the carriage house two adults. There is one bathroom in the cottage and one in the carriage house. Please read through all the information in the 'Description' section below before booking.

Ivy Rose Cottage nestled b/t Cville & Vineyards

The Ivy Rose Cottage bestows an exceptional ambiance that will captivate your heart. Whisk yourself away to this two bedroom cottage located in Ivy halfway between the Shenandoah Park/Brewery Trail and Charlottesville, home of UVA. The Ivy Rose Cottage, designed and handbuilt by the hosts, is an enchanting mix of cypress, timber frame, copper trellis work, pergolas and other architectural treasures. Fully equipped kitchen and a washer/dryer for those lengthier stay conveniences.

Luxury Cottage | Outdoor Tub + Mountain Views

Soak in a private outdoor bathtub beneath the stars, wake to mountain views from your king bed, and open an entire wall of glass to bring the Blue Ridge Mountains inside. Welcome to The Cottage at Perkins Hollow Retreat! Located in Nelson County, just minutes from the Nelson 151 Brew Trail, award-winning wineries, breweries, hiking, and only 25 minutes from Charlottesville, The Cottage is the perfect destination for a romantic getaway, anniversary, honeymoon, or peaceful retreat.

Unit 1_Expansive Luxury Suite for up to 4 Persons

Take a journey to Albemarle County and experience historical sites and luxurious accommodations. Sonsak is uniquely situated on the Thomas Jefferson Parkway; nears area's most celebrated landmarks, including Monticello - Home of Thomas Jefferson, directly across Michie Tavern and near Ash Lawn - Home of James Monroe, Carter Mountain Orchard and numerous Vineyards. Embark on a 'Journey Through Hallowed Ground', an unforgettable experience that's packed with history and beauty.