Family-friendly vacation rentals in Charlottesville

Cozy Mountain Cottage on Brew/Wine Trail-King Bed

Welcome to the Sugah Shack, a cozy, beautifully appointed new construction cottage nestled in the foothills of the Blue Ridge Mountains! Located midway on the Brew Ridge Trail, but 500 yards off the byway, so guests have a quiet retreat. Perfect for romantic getaways, destination telework space, or families exploring this outdoor paradise community. Stunning property boasts beautiful vistas with sweeping 300-degree mountain and a year-round calendar of outdoor activities. GAS FIREPLACE/FIREPIT

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.

Belmont Home with Hot Tub - steps from Downtown

The perfect destination for your Charlottesville visit in the hip neighborhood of Belmont, where you can read on the loggia with great views or in the hot tub on the patio. From this modern home, you can walk to the best restaurants the city has to offer as well as the popular Downtown Mall and IX Art Park. The University of Virginia and Monticello are each just a short drive, and the home is convenient to the Monticello Wine Trail and Skyline Drive. See below for link to basement apt. listing.

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.

Elk Mountain Overlook: Breathtaking Views

Mountaintop overlook with jaw dropping views and camp themed interior design. Perched upon Elk Mountain just off the Blue Ridge Parkway this petite chalet is under 30 min from Charlottesville, 10 min to 151 vineyards/breweries/cideries, and 10 min to Waynesboro. Relax in this natural retreat featuring 2 king bedrooms, 2 person soaker tub, double headed shower, and ample kitchen w/many extras. Take in the views from the large deck, firepit, under porch swing, or mountainside adirondack chairs.

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.

3BR / Pets Welcome / Fenced Yard / Fiber Internet

Sitting atop the neighborhood, Monticello can be seen from our Ridgetop home. Convenient to all parts of Charlottesville, including Downtown, UVA, and Hospitals. Local parks offer swimming, boating, & are all walkable. The fenced yard allows for a safe space for dogs and the private patio is perfect for relaxing. The home offers an open design in the kitchen, living & dining room. Bath has a modern tile with a jacuzzi tub. Fast TING fiber internet. Freshly painted. Big Green Egg grill

The Bungalow at Afton Mountain Retreat by Veritas

Welcome to The Bungalow at Afton Mountain Retreat in the heart of Brewery Trail/Route 151, Vineyard country and the foothills of the Blue Ridge Mountains. The Bungalow is located 1/4th mile from Veritas Vineyard. It is within 10 minutes to every brewery, vineyard, distillery and cidery along Route 151 Crozet, 1 mile from the newly opened Blue Ridge Tunnel and 20 minutes to Wintergreen Resort for winter fun! Completely remodeled and ready to spoil the best guests who simply want to unwind.

Walk DT | Pets | Soaking Tub | Parking

The High‑Note Craftsman Cottage – live like a local in downtown Charlottesville Stay in a charming and pet friendly Craftsman cottage just minutes from Charlottesville’s Downtown Mall. Enjoy a soaking tub, fast Ting fiber Wi-Fi, and rare free parking — perfect for couples, families, and remote work travelers. This bright, comfortable home blends historic character with modern amenities, creating the ideal base for exploring Charlottesville, UVA, wineries, and the Blue Ridge Mountains.

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.

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.

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!