Cottage holiday rentals in Charlottesville

Cozy Mountain Cottage on Brew/Wine Trail-King Bed

Welcome to the Sugah Shack, a cozy, beautifully appointed new construction cottage nestled in the foothills of the Blue Ridge Mountains! Located midway on the Brew Ridge Trail, but 500 yards off the byway, so guests have a quiet retreat. Perfect for romantic getaways, destination telework space, or families exploring this outdoor paradise community. Stunning property boasts beautiful vistas with sweeping 300-degree mountain and a year-round calendar of outdoor activities. GAS FIREPLACE/FIREPIT

Tranquil Cottage and Art Studio

Enjoy a comfortable, well decorated home, breathtaking sunsets over the Blue Ridge mountains, 4 miles to downtown and minutes to many vineyards, shows, and more. During your stay here, experience the lifestyle of town and country. Walk our country roads, feed the horses, enjoy top 2% mountain views, and utilize our new art studio for an hour indoors or plein air. Sorry no pets or children under 8 for safety. Price based on 2 people. Stays of more than 3 nights add $20 for cleaners. See you soon!

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.

Private Forest Cottage near Pippin Hill/Wineries

Completely renovated in 2019, our private forest cabin in the heart of the Blue Ridge mtns and Albemarle wine/brewery country is perfect for getaways, weddings and outdoor enthusiasts. A picturesque oasis with an eco-friendly design (Separett composting toilet!), the cabin has a loft with queen bed and sleeper sofa in living area, 3 porches, private parking, neighborhood swimming pond, hiking trails right out your door, Crozet 10 mins, Wintergreen 30 mins; Cville 20 mins, Shenandoah 15 mins.

Idyllic Cottage Retreat

⭐️ Condé Nast Traveler Approved ⭐️ Cozy cottage nestled on a historic 400-acre Blue Ridge Mountain farm abutting Shenandoah National Park. Every space inside this cozy cottage is creatively styled, with tons of perfectly imperfect charm. Outside, a hammock beneath the elm trees, fire pit and grill, all allow for enjoying the splendor of this peaceful enclave. Excellent day-tripping to many of central Virginia's celebrated wineries and breweries, as well as scenic drives and hiking trails.

Meade Cottage

Lovely 1940s cottage located in beautiful downtown Charlottesville. Less than 1 mile to the downtown mall, with coffee shops and top Belmont restaurants close by, some within a 5 minute walking distance. The cottage is across the street from Meade Park and the Wednesday farmers market from May to September. Perfect for a romantic couples getaway or a family vacation. The space is ideal for a traveling professional in Charlottesville and needing to be close to the University or the Hospital.

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.

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.

Lake Haven Cottage

Make yourself at home at our peaceful 1-bedroom cottage that has everything you need for your trip to the Blue Ridge Mountains. The cottage comes with heating, AC, Washer+Dryer and DIRECTV. During your stay, you can also enjoy using a convenient private bathroom, kitchen, and living room. Our Airbnb is within driving distance to UVA, the Skyline Drive & Shenandoah National Park, local wineries, craft breweries and much more!

Hawkwood House King Bedroom

Hawkwood House is close to Charlottesville, VA. It is in a 100-acre wood. Two guests share downstairs bedroom. Guests may use upper floor only with prior arrangements. It is a very quiet, peaceful setting. It is located near historic sites from colonial times of the United States and the Civil War and near Charlottesville VA and homes to three early US presidents (Monticello, Ash Lawn and Montpelier).

Woolen Mills Cottage- 2 Beds, 1 Bath, Full Kitchen

This renovated 2 bedroom, 1 bath home includes a kitchen with full size fridge, range with convection, coffee pot and microwave. Everything you need to prepare meals and close to restaurants too. Living room and dining room spacious enough to easily accommodate 6. Shower with tub and two queen size beds. Towels and linens are provided for your stay. Pet friendly house with a large, flat back yard.

Country Cottage with Modern Amenities

Looking for a relaxing weekend getaway in Virginia's countryside? Welcome to the Shade Tree Cottage! This home dates back to the Civil War and is full of cottage vibes. Located just a 3-minute drive from downtown Gordonsville, the home is the perfect combination of rural retreat and launch pad to some of Central Virginia's best wineries, historic sites, and attractions.