Holiday rentals in Shadwell

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Top-rated holiday rentals in Shadwell

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A sweeping landscape showcases rolling green hills under a partly cloudy sky. Tree-lined fields extend towards a winding road that leads to nearby structures, set amidst nature's tranquility.
Farm stay in Charlottesville
4.9 out of 5 average rating, 173 reviews

Jefferson Cottage quiet farm close to everything

The cottage circa 1802 offer a peaceful private setting on a historic horse farm once part of Monticello with close proximity to wineries (10 minutes), town (12 minutes), Rivanna River borders the property, Carter mountain (8 minutes) and many other activities. A "Jimmy Buffet" salt water pool complex has a private Jacuzzi for each unit, double bars, two fire pits, frig ,full bath/shower/changing room) There is a private lake (catch and release fishing) and many places to walk on the property.

Top guest favourite
A historic two-story estate is visible beyond a cobblestone driveway, framed by lush green trees. In the foreground, a stone statue of a dog holds a basket of fruit, adding charm to the property entrance against a clear blue sky.
Home in Charlottesville
4.98 out of 5 average rating, 110 reviews

Rivanna Farm Estate North I Pickleball I Pool

This historic 42-acre country estate features four distinct residences, three of which are Airbnb rentals. The "North” offers beautiful views of the Blue Ridge Mountains and includes 4 bedrooms: 2 bedrooms with queen beds, and another with 2 twin beds on the main floor, and an additional queen bedroom upstairs. The second floor has a full kitchen, living room, & dining area. On the lower level is a yoga studio, game room, outdoor patio area w/seating, and charcoal bbq. (Charcoal not provided)

Top guest favourite
A comfortable living area features a gray sofa adorned with patterned throw pillows. A modern table sits in front, displaying a potted plant and a decorative tray. Colorful artwork hangs above the sofa, while a lamp provides soft lighting in the corner.
Home in Keswick
5 out of 5 average rating, 113 reviews

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.

Top guest favourite
A charming farmhouse is set on a spacious green lawn, surrounded by trees. Featuring a welcoming front porch with railings, the house displays multiple peaked roofs and large windows, inviting natural light. The grounds offer ample space for outdoor activities.
Home in Charlottesville
5 out of 5 average rating, 200 reviews

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!

Top guest favourite
A single-story home with light blue siding is set against a clear sky. A vibrant door adds a pop of color to the entrance, which is framed by landscaped flower beds. A paved walkway leads up from the driveway, inviting visitors towards the front entrance.
Home in Woolen Mills
4.97 out of 5 average rating, 110 reviews

3BR / Pets Welcome / Fenced Yard / Fiber Internet

Sitting atop the neighborhood, Monticello 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. Freshly painted. Big Green Egg grill

Guest favourite
An open-concept living space is featured, showcasing a cozy seating area with a light grey armchair and a small side table. A dining table with black chairs is visible in the background, along with dark cabinetry and decorative items on display.
Home in Charlottesville
4.98 out of 5 average rating, 128 reviews

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.

Top guest favourite
The dark wooden cabin, framed by lush greenery, sits at a hillside location with panoramic mountain views. A deck extends from the cabin, featuring a hanging basket chair. A warm sunset casts a golden hue across the sky, enhancing the serene atmosphere.
Cabin in Free Union
4.99 out of 5 average rating, 202 reviews

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!

Top guest favourite
A welcoming exterior of a curved house is presented, featuring a light stone pathway leading to a front porch. Two white rocking chairs are positioned in front, with decorative planters filled with greenery on either side. The backdrop consists of lush trees and a blue sky.
Home in Charlottesville
4.98 out of 5 average rating, 145 reviews

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.

Top guest favourite
An aerial view captures a spacious guest house nestled among trees displaying vibrant autumn foliage. The surrounding landscape features a mix of green and colorful leaves, with an open area visible beside the property. Outdoor amenities are discernible, blending harmoniously with the natural setting.
Guest house in Troy
5 out of 5 average rating, 210 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. 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.

Top guest favourite
An open living area features a low stone coffee table atop a vibrant red and patterned area rug. A gray sofa offers comfortable seating, and a small potted plant adds a touch of greenery. A TV hangs on the wall, while a doorway leads to the bedroom.
Flat in Locust Grove
4.9 out of 5 average rating, 273 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!

Top guest favourite
A welcoming cottage entrance features a covered porch with a white railing, surrounded by lush greenery and colorful flowers. A stone pathway leads to the door, inviting guests into a serene outdoor space with various plantings.
Cottage in Charlottesville
4.99 out of 5 average rating, 187 reviews

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.

Top guest favourite
An open living area is highlighted by a light-colored sofa and a wooden coffee table. A spiral staircase leads to an upper loft, while a dining table with wooden chairs sits nearby. Large windows provide ample natural light, illuminating the space.
Home in Charlottesville
4.98 out of 5 average rating, 595 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).

Popular amenities for Shadwell holiday rentals

  1. Airbnb
  2. United States
  3. Virginia
  4. Albemarle County
  5. Shadwell