Vacation rentals in Overton

Newly Built Luxury Home 3min to UVA–Near Downtown

Walk to UVA, Stadium & Downtown! 🚶‍♂️ Our 3-story, 5BR retreat is the ultimate Charlottesville base for fans, families & wine lovers. ✨ Location: 🎓 UVA: 3m drive | 10m walk 🏈 Stadium: 4m drive | 15m walk 🛍️ Downtown: 5m drive | 18m walk 🍷 Wineries: 12-20m drive ✨ Amenities: ☕ Breville Barista: Pro espresso & beans 🎮 Fun: PS5,Foosball,Netflix,Disney+& Hulu 🏋️ Gym: Rowing machine, arm twister & yoga mat 👶 Family: Crib & kid gear 🅿️ FREE 2-car driveway + unlimited street parking! 🎓🏈🍷

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

Spacious modern house with a brand new rooftop deck overlooking Carter Mountain and Monticello. 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 from each level 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 (3.5 mi/5 min+) & breweries.

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!

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.

3BR / Pets Welcome / Fenced Yard / Fiber Internet

Sitting atop the neighborhood, Monticello mountain 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. Big Green Egg grill

The Cottage at Eastwood Farm and Winery

The Winery Cottage at Eastwood Farm and Winery is located on the historic Woodland estate, built and owned by Jefferson builder, John Dunkum in 1810. Our 78 Cville acres include our family’s winery with indoor (year round) and outdoor (Apr-Nov.) tasting rooms, extensive wooded trails, incredible mountain views and apple orchard. Nestled on the same ridge as Monticello, Carter's Mtn, Jefferson Vineyards, Blenheim and Trump Vineyards. Five minutes to Belmont and Downtown Mall.

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.

Cavalier Cottage-3 BR/Bath, Calm Amid UVA Grounds

Fully-updated, custom home in premier location. Warm hardwoods, lots of light, comfortable sofas & beds, easy check-in -- we strive to make your stay restful and refreshing. Nestled between Scott Stadium & JPJ, O'Hill & the Rotunda, wine country & the downtown mall, you could not be closer to the action yet in a quiet, residential neighborhood. The perfect place for any & all Cville/UVA events, work trips, reunions, weddings, family vacations, college visits, etc.

The Loft at Minor Mill - Private loft apartment.

Our place is a newly constructed barn loft in our 1960's barn. Enjoy beautiful views of the surrounding countryside from large windows and a private balcony. The barn is surrounded by our horse pastures and neighboring fields. Self check in with the key lockbox. This loft is separate from the main house where we live. Private parking and entrance for our guests directly outside of barn loft (this is separate from the main house driveway).

10 Vineyards Within 10 Mi, EV charger & Mini Goats

Upscale boutique Carriage House on a 25-acre farm in Charlottesville Wine Country. 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. 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.

Scenic Private Farm House Great for Large Groups

CHURCH FIELD HOUSE. Large 5 bedroom, 4 bath house with sweeping 360 degree views featuring beautiful pastoral and mountain landscapes on a 250 year old family farm in the Southern Albemarle Historic District. Enjoy large windows in almost every room with unobstructed western views. Large outdoor deck and a separate fire pit area are favorite places to view spectacular sunsets over the Blue Ridge Mountains.

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.