Vacation rentals in Overton

Belmont BnB ~ 2BR/1BA ~ Comfort & Convenience

Welcome to our well-appointed, centrally located 2 BR/1BA apartment! This cozy spot, with comfy queen beds, full kitchen, and cottage garden is a perfect homebase to relax in after a day of exploring. Set out on foot to: • Belmont Park (2 blocks) • Belmont Restaurants (15 min) • The Rivanna Trail (5 min) • The Downtown Mall (20 min) Short drives to Monticello (< 4 mi), grocery stores (1-2 mi), and UVA (2 mi). Your hosts are readily available in the above apartment should you need anything!

One Level Living at Shadwell Terrace

Set in the heart of Wine Enthusiast’s Wine Region of the Year, this newly renovated 2-bedroom, 800 sq/ft terrace level flat with separate entrance, is located in a private setting in the Keswick area. Close to Downtown Charlottesville, we are adjacent to Clifton Inn and Glenmore and minutes to Keswick Hall. After exploring many of Virginia’s wineries, breweries, and historical sites, kick your feet up between the trees in the hammock or share your adventures online with our high speed Wi-Fi.

Unit 4 - Luxury King Suite with Private Balcony

Experience luxury and a unique journey through history at Sonsak - a newly renovated guesthouse in Albemarle County. Situated near the esteemed landmarks of Thomas Jefferson Parkway, Monticello, Ash Lawn and Michie Tavern, Ash, Sonsak is in a renowned area of historical significance. The property dates back to 1942 and has since been exquisitely renovated with lavish furnishings and modern amenities.Treat yourself to a stay at Sonsak and leave with lasting memories of comfort and beauty.

Honey B - Beautiful loft near UVA, Monticello

Best of both worlds! In beautiful nature but close to UVA, Monticello and downtown. Honey B (Honey House 2) has a lofty feel with the footprint of a small house. High ceilings and several skylights allow for light and privacy in the quiet neighborhood, Located on the southwest side of Charlottesville, just 7 minutes to Scott Stadium, UVA campus, and restaurants, 10 minutes to historic downtown mall, Thomas Jefferson’s Monticello and central to many major wineries and breweries.

Small cozy Cabin in the foothills! Dogs welcome!

Escape to this private guest cabin for two in the rolling hills of Esmont, just outside Charlottesville and Virginia wine country. Set on 60+ acres of peaceful farm and woods, this quiet retreat offers privacy, wildlife, and open skies. Walk over two miles of private trails (when open) and unwind by the fire pit under the stars. Perfect for a romantic getaway or Blue Ridge escape. No cleaning fees—please tidy up. Dog friendly with a $50 NON-REFUNDABLE fee; dogs must

Convenient Rustic Cabin near Wineries

I’m located 6 miles from Scottsville, 15 miles from Charlottesville, 25-30 minute drive. A pasture of cattle is not too far away you can hear the mooing at times and see sightings of deer quite often. It’s a private and quiet location. Two large rivers, James and Rivanna offer recreational activities. Rustic cabin, country located. Clean and cozy with a well stocked kitchen with all your cooking needs. If not, leave suggestions on what is missed. Thank you.

10 Vineyards Within 10 Mi, EV charger & Mini Goats

Upscale boutique Carriage House on a 25-acre farm in Charlottesville Wine Country. Just minutes from top vineyards, this light-filled retreat features elegant rustic design, new furnishings, and spa-like comfort. Enjoy visits with Nigerian dwarf goats and free-ranging chickens—plus fresh eggs in season. Perfect for romantic getaways or remote work, with WiFi, cozy touches, and the beauty of nature all around. Tesla wall connector charger available for guests.

Mountain-view hot tub near downtown Cville

The Inner Hippie Garden is a studio suite in a quiet neighborhood fitting two people comfortably. Minutes from vibrant historic downtown Charlottesville and vineyards, wineries and music halls. Check out the Inner Hippie Guidebook in listing. Man-cave for book and 60s music -lovers, full bathroom with tub/shower. Bed and living room space are separated by shelving unit (see photos) Queen bed (see photos) Private Hottub overlooks the mountain.

Luxury tiny house 3 min from UVA

La Casita, a new tiny home, combines modern luxury with a prime location near UVA, wineries, and Monticello. Designed to offer custom furnishings and luxurious touches, La Casita is situated in the residential, pedestrian-friendly neighborhood of Fry’s Spring, conveniently located near I-64. Residents can enjoy easy access to restaurants and Scott Stadium. Amenities include high-speed internet and other modern conveniences.

Tranquil Estate Cottage + Art Studio

Guests consistently say the sunsets alone are worth the stay! We've had anniversary trips, proposals, creative retreats, and gal pal gatherings looking for fun. This area boasts award winning vineyards, gardens and history buffs enjoy Monticello and Montpelier. Our peaceful cottage offers the perfect space for couples, creatives, and anyone craving beauty just 10 minutes from downtown C'ville. *Read "Your Property"

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.