Vacation rentals in Overton

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.

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.

Thomas Jefferson Pkwy - Gateway to Monticello

Farmhouse on 14 acres offers closest proximity to Monticello (4 minutes away). Jefferson Vineyard (1 min), Ash Lawn (3 min), Carter's Mountain & Michie Tavern (5 min), Downtown Open-Air Mall (14 min). Relax with a cold drink on the front porch or enjoy views of the mountains and pond from the back deck. There is plenty of space to breathe here. Full kitchen & laundry. Feel free to snack on whatever we have. Great views & country feeling but close to everything. Relax & make yourself at home!

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!

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.

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.

Beaver Pond Farm - Near Charlottesville

Relax at this unique and tranquil getaway. Sit on the screened in porch and enjoy the sights and sounds of nature while you enjoy a beverage. Visit the Downtown Mall, Monticello, a Winery, a Brewery, or UVA (20 min). Enjoy a dip in the pool (JUN-AUG) or relax by the firepit - perhaps joined by a Great Pyrenees for cocktails. Feel like staying in - SmartTVs with YouTubeTV (which includes local channels) and Gig-speed Internet await. Easy checkout. No cleaning fee.

Charming St. Charles

A beautifully renovated basement apartment in a family friendly neighborhood. Two blocks from our neighborhood park, with a connector to the Rivanna Trail. A 30 minute walk downtown, a bus stop one block away, & bike & scooter rentals make it much faster! Easy access to 250 bypass make Downtown & 29 North equally convenient destinations! Perfect for a couple with a young baby or toddler! Guests must acknowledge that footsteps and sound from our living area can be noisy!

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.

Cottage in the Country (close to UVA!)

Stay at our lovely cottage beside Stonybrook stream! Only 2 miles to the city of Charlottesville. You are invited to explore the land and enjoy the brook that runs through it. Guests love the fire pit and large lawn for playing with the kids. The large, covered outdoor entertaining area is for you to use as well! Turn on the party lights and enjoy the evening. A drop in to the Rivanna river is only a mile away at Darden Towe park for tubing, kayaks and more.