Vacation rentals in Overton

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Top-rated vacation rentals in Overton

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Guest favorite

Guest suite in Charlottesville

4.98 out of 5 average rating, 364 reviews

2 King Beds/1XL Twin, 2 BDRM Apt Close to Downtown

Basement apt in a quiet neighborhood 1 mile from UVA Hospital and Downtown Mall and 2 miles from UVA. Two bedrooms (2 memory foam King beds new in Spring '24, a Twin XL bed, & a toddler bed), a full kitchen, coffee/snacks, washer/dryer, bathroom, toiletries, a living area with a Roku TV & Netflix, free parking, & a private entrance with a patio. Our guests love the value, amenities, & cleanliness! No smoking of any kind. Please read note about the slope to the entrance and potential for noise.

Guest favorite

Cabin in Schuyler

4.98 out of 5 average rating, 182 reviews

Cozy cabin for 2 w/mountain views & trails

Cozy cabin in the woods with beautiful mountain views from covered back deck! Perfect for nature lovers, couples, singles. Ideal for a peaceful escape or visiting local wine/brew trail. While remote, also a convenient base to visit area attractions, hikes & easy drive to C'ville. Relax on the covered back deck watching the sunset and wildlife. Over 2 miles of wooded trails on property for guest use. 15-20 min walk through woods trails (part of this walk is on a hill) to access Rockfish River.

Guest favorite

Cottage in Charlottesville

5 out of 5 average rating, 129 reviews

Honey B (Honey House 2) Newly renovated near UVA

Newly renovated, clean and comfortable with many amenities. Honey B 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 of Sherwood Farms. Located on the southwest corner of Charlottesville, just beyond UVA campus, 7 minutes to Scott Stadium, UVA and restaurants, 10 minutes minus plus to everything Charlottesville : historic downtown mall, Thomas Jefferson’s Monticello, Many wineries and breweries.

Guest favorite

Guesthouse in Troy

4.99 out of 5 average rating, 157 reviews

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. Take a walk on miles of trails that are adjacent to the property. 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 the horses for cocktails. Feel like staying in - SmartTVs and Gig-speed Internet await. Easy checkout. No cleaning fee.

Guest favorite

Guesthouse in Charlottesville

4.91 out of 5 average rating, 145 reviews

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.

Guest favorite

Tiny home in Scottsville

4.98 out of 5 average rating, 388 reviews

Rare Find: Private Animal Sanctuary & Tiny Cottage

Voted one of the coolest Airbnbs in Virginia by Trips to Discover! Voted one of the top 12 tiny houses in Virginia by Trip101! Peaceful, safe, and magical are just a few words guests use to describe our farm. It's the perfect retreat to relax and reconnect with yourself and nature. Enjoy exploring the farm, spending time with our animals, and stargazing by the firepit. We invite you to soak in all the richness the farm and animals have to offer. We’re also 420 friendly.

Guest favorite

Rental unit in Charlottesville

4.89 out of 5 average rating, 208 reviews

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!

Guest favorite

Tiny home in Charlottesville

4.94 out of 5 average rating, 698 reviews

Oxford Cottage: Cville’s favorite tiny home!

This 350 sq ft cottage is a tiny home concept space, boasting an airy entry, living area, storage landing, kitchenette, bathroom and sleeping loft. Perfect for a romantic getaway, a work retreat, a stop through town on the way to another location, a small family, or a group of friends participating in the many events held in Charlottesville- weddings, concerts, triathlons. Accommodates 1-4 people looking for a relaxed, stylish, modern and comfortable place to stay.

Guest favorite

Tiny home in Scottsville

4.91 out of 5 average rating, 220 reviews

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.

Guest favorite

Farm stay in Esmont

4.93 out of 5 average rating, 173 reviews

Small cozy Cabin in the foothills! Dogs welcome!

Peace and tranquility is what you will find in this guest cabin for two nestled in the rolling hills of Esmont. The 60+ acre farm is teeming with wildlife. Spend your morning walking over two miles of private trails (when open) throughout the property and enjoy evenings sitting around the fire pit. Hate cleaning fees? Me too, so I've decided to eliminate it for my rental.....just please clean up after yourselves. Dog friendly with a $50 NON-REFUNDABLE deposit.

Guest favorite

Barn in Charlottesville

4.98 out of 5 average rating, 516 reviews

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).

Guest favorite

Guesthouse in Charlottesville

4.95 out of 5 average rating, 286 reviews

Walk to UVa from our Charming Tiny Home

Walk to UVa from this brand-new 250sq ft "tiny home". Its perfect for game days (1 mile walk along sidewalks to Scott Stadium) or a stylish alternative to hotels for events or work travel! This cottage features a open floor plan with vaulted ceiling, a living room with TV/WiFi, kitchenette, bathroom with tub/shower and sleeping loft. Accommodates 1-4 people looking for a modern, comfortable and centrally-located place to stay.