Family-friendly holiday rentals in Charlottesville

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.

Shenandoah Getaway Cabin on 5 Acres w/ *Hot Tub*

Our Log Cabin has EVERYTHING you need for your mountain vacation! Miles of gorgeous mountain views off the large wrap around porch. *Outdoor Hot Tub *Indoor Wood Burning Fire Place *15 minutes from Shenandoah National Park *30+ Local Wineries!! *Outdoor Firepit *1GB WIFI and Huge TVs! *Close to UVA/ Charlottesville *Full Kitchen *Large, Private Deck with Mountain Views *Propane Grill *Outdoor Heater *Plenty of Space to Park Cars *Hiking *Maybelle's General Store less than a mile away

Rooftop*Mountains*Lake/Near Monticello/DT/Wineries

Spacious modern house with a large furnished rooftop deck overlooking Monticello & Carter Mountain. Two spacious primary bedroom suits (one on each floor) with attached decks, plus additional two bedrooms and a full bathroom on the 2nd floor. Located in a quiet neighborhood. Backs up to a lake for beautiful views and tranquil environment. Convenient location - minutes away from Monticello (2 mi/4 min), downtown (2.5 mi/6 min), UVA (3 mi/9 min), wineries (closest: 3.5 mi/5 min) & breweries.

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!

Shepherdess Cottage

Charming cottage located in Scottsville, Virginia on a 93 acre sheep farm. It is located 19 miles from Charlottesville. The Shepherdess Cottage is tiny, relatively private and offers beautiful views. We are a working farm so you may encounter us, but will respect your privacy as much as we can. You are welcome to "free range" with our sheep and enjoy exploring the property. Sometimes our lambing season (pretty much year-round) will offer bottle babies that you can feed and cuddle.

Log Cabin w/ Views! 8+ Acres! Pets!

Charming log cabin with amazing views of the Blue Ridge Mountains. Only 15 minutes to Route 151 brew trail and 25 minutes to UVA or Wintergreen Resort. Please note that while the cabin offers an idyllic hilltop setting, access requires a 4-wheel drive vehicle due to the steep gravel driveway. For guests without such vehicles, designated 2-wheel drive parking is available halfway up the driveway. Refer to “Other details to note" and “House Rules” prior to booking.

Main Street Downtown Balcony Apartment

Welcome to the center of Cville! Our newly renovated second floor balcony apartment is centrally located on historic West Main Street in the heart of Midtown. We are seven blocks from UVa campus/hospital, four blocks from the Downtown Mall and directly across from the Amtrak station. The free trolly stops are right outside your door along with many of Cville’s best reviewed and acclaimed restaurants. Join us and experience Cville from the inside out.

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!

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.

Charming Cottage at Golden Hill

Enjoy our lovely handcrafted cottage in its wooded, peaceful setting with its new keyhole-style herb garden. Just a mile off the Keswick exit of I-64 near Charlottesville, UVA, Monticello, many wineries and historic sites, this conveniently located property includes walking trails, hilarious chickens, beautiful gardens and a new playset for children. High speed internet is an added bonus.

2 King + 1 Twin XL Near 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