Holiday rentals with breakfast in Charlottesville

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.

The LoriAnn, A Boutique Stay New Sleep Number Bed

This beautifully restored 1940’s home in the City of Waynesboro is just a short drive from the Blue Ridge Parkway. Modern amenities, light complimentary breakfast items and assurance of comfort awaits! Enjoy one of a kind Autographed Movie and TV Memorabilia. The spacious front porch is yours to enjoy including a 100 yr old porch swing that belonged to my Great Grandmother. Along with the Parkway & Skyline Drive, enjoy Restaurants, Breweries, Vineyards, movie theaters and exploring Route 151.

Tiny Luxury Retreat: Lake, Hikes, Brews & Vines

Welcome to our luxurious tiny house nestled in the heart of Nelson County, Virginia. This enchanting retreat, surrounded by the majestic Blue Ridge Mountains, offers an unparalleled experience in a landscape dotted with wineries, breweries, distilleries, and sprawling farmland. This luxury tiny house was built in 2022 and is available for couples, solo travelers, or a small family wanting to explore this beautiful stretch of the Blue Ridge Mountains. FREE Electric Vehicle Charger on-site.

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.

Farm Cottage just outside town of Orange.

Charming 1920's cottage on a large farm just outside the town of Orange. Completely renovated and updated. Convenient to vineyards, battlefields, wedding venues and popular tourist destinations. Bucolic setting, very private. Spaces to enjoy the out of doors. Less than 2 miles to in-town wedding venues and Rounton Farm. Less than 4 miles to Inn at Willow Grove. 5 miles to Montpelier. Less than 7 miles to Grelen. 10 miles to Gordonsville. 12 miles to Barboursville. 19 miles to Mineral.

Little Forest Tiny Cottages in Free Union

Enjoy the breathtaking views of the Blue Ridge Mountains on this 26 acre Olde English Babydoll Sheep farm right from your window. Our farm is a haven of peace and serenity in a secluded but centrally located area just 18 miles northwest of Charlottesville. Wake up to delicious farm fresh breakfast from our eco-friendly farm. Take pictures of fluffy sheep and angora rabbits grazing on rolling hills. Hike our private trail. Breathe in the fresh mountain airs. Sleep in. Slow down. Relax.

Walkable/Peaceful/Spacious Suite/Downtown/UVA/1 BR

Enjoy private entry, peaceful, 3 blocks to Downtown Mall. 2nd floor suite, wood floor, 1 queen bed, sofa, electric fireplace, study/desk-remote work, double bathroom-step-in shower, 4' clawfoot tub. Private coffee room/library: compact refrigerator, microwave, ceramic cookware, full dish set, flatware, wineglasses, electric kettle, pour-over coffee Chemex, locally ground coffee, bakery breakfast bread, NO KITCHEN/no stove-Support local restaurants! By request:Extra bed for $35/night.

Delightful one bedroom treehouse with king bed

You'll love this unique and romantic escape. Come and disconnect from the world and reconnect with each other in the Treehouse at Backabit Farm. You can enjoy the indoor fireplace or outside propane fire pit! Private deck for gazing at the stars or watching the wildlife. Two person hammock tucked under the trees! Inside you will find king bed with a view out of the three large windows, loveseat, tv, microwave, small fridge, coffee station and quaint bathroom with tiled shower.

Wakefield Ct | Private Parking spots | Fast WiFi

Cozy stay in an updated colonial style house on a quiet street. Short drive from great local spots along Downtown Cville, UVA Corner, Monticello, Blue Ridge Parkway, The Appalachian Trail, breweries and local wineries. An excellent choice for hosting small gathering with good yard space and pouch. A wonderful stay if you like to be close to all the attractions Cville has to offer, but still far enough to enjoy peace and quiet. Thank you, for your time and consideration.

The Barn at Haden near Wineries and C'ville

The Barn at Haden is a custom well appointed finished 2 bedroom, 1 full bath space elevated above a detached 3 car garage with a large outdoor private deck. It features a fully equipped gourmet kitchen with high end finishes. Whether staying for a night or for the weekend, it is an experience to enjoy the easy living Crozet has to offer. Walkable/bikeable to downtown Crozet, 2 miles to King Family Vineyard & Chiles Peach Orchard and 15 minutes from Charlottesville.

Unit B -Tatum’s Retreat -SAUNA- Hiking-Wineries

Beautifully renovated and cozy home in Madison, VA. Unit B is the bottom level of a duplex offering a peaceful setting, amazing views, close to wineries, wedding venues, hiking. SAUNA! Near Early Mtn Vineyards, Prince Michelle, Yoder's Market, Bald Top Brewing & Plow & Hearth. A 30 min drive to Charlottesville, Greene, Shenandoah Nat. Park, Culpeper & Orange, w/ shopping, restaurants, breweries, hiking, antiquing, site seeing & more. Dogs allowed- $30 fee.

The Loft at Firefly: Studio Apt

This unique & fun studio apartment is above FIREFLY Restaurant + Game Room, located in Charlottesville's Woolen Mills neighborhood. You're half a mile to downtown Cville, Ting Pavilion, the Rivanna River & trail, and the popular Belmont neighborhood. Major perk: while you're here you'll enjoy 20% off all food at FIREFLY - Open for lunch & dinner Tues-Sat. If you'd prefer to cook, there's a full kitchen in the apartment. Sleeps up to 5.