Vacation rentals in Cunningham

Bluebird Cottage A: Dogs OK, Near Charlottesville

Simple pleasures, affordable – Bluebird Cottage pristine and uncomplicated space with charming décor provides everything you need for a comfortable stay. Perfect for guests seeking a yard with firepit and cornhole game; bring your doggy! Relax in peace in a quiet neighborhood where a fully equipped kitchen, washer-dryer, outdoor dining, patio, electric fireplace, outdoor kennel for your furry friend, fast Wi-Fi, and more await you. Close to Private Lake Monticello, CVille. $100 flat fee pet fee.

Green Willow Farm apartment near Monticello

*Winter update: Jan/mid-March. Our fairly long flat gravel driveway is hard to navigate in snow. AWD, or heavier cars, are helpful. We will shovel some, allow sun to melt the remaining. FYI when booking. Spacious farm apartment(walkout apt below our living space) in the rolling hills of Virginia. Galley kitchen. Large fireplace. Private entrance. Stone patio. Close to downtown Charlottesville and UVA(+/- 8 miles). A few miles from Monticello, Many vineyards, and Carter's Mountain Orchard.

Guest Suite by Wineries/Orchards/Cville/Monticello

Welcome to Deer Hideout Retreat! We are located in Palmyra, Virginia, on two acres of land. There's an abundance to see and to do around here, and we hope you choose our home for your stay. We are far enough outside of the city to enjoy the peace and quiet, but just a short drive to all the action. We are close to Monticello, James Monroe's Highland and 28 minutes away from the city center of historic Charlottesville. There are plenty of vineyards all around us and a couple of orchards, too.

Love 2B close 2U: Quiet, comfy Apartment & Pool!

Quiet, rural setting in neighborhood culdesac. Located off Rt 53, approx 15 mins from Monticello & FUMA. Basement of home, w/private entrance is a 1000 square foot apartment with a large full bathroom, large bedroom with 2 Queen size beds, open floor plan with living, dining area and kitchen. Space includes a large screened in porch w/ bed swing, patio area & swimming pool. No diving - deep end 6ft. View of woods on back of property w/ sunrise through the trees in morning. Lovely retreat.

The Cottage at Hardware Hills Vineyard

Head for the Hills! The Cottage at Hardware Hills Vineyard sits atop the property alongside the main estate house. Bask in Virginia sunsets over the vines. Take a short hike down to the Hardware River where you can dip a toe in or try your hand at fishing. On weekends, you have a family-owned winery right in your front yard to stroll down and sit by the vines to enjoy delicious wines. Centrally located to many wine trail attractions and all that the Charlottesville area has to offer.

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.

Rare Find: Private Animal Sanctuary & Tiny Cottage

For animal lovers seeking an exclusive and unique getaway, this boutique Airbnb in Scottsville offers a tranquil escape where guests can unwind in nature and connect with the sanctuary’s resident animals. Recognized by Northern Virginia Magazine, Trips 101, and Trips to Discover as one of Virginia’s most distinctive stays, this thoughtfully curated retreat features cozy furnishings, charming handcrafted details, and an expansive window that showcases views of the animals.

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.

Black Cat Retreat

Private entrance. upstairs, Lots of light, Wrap around deck! Full private bath in room. Large room with a small kitchenette. Refrigerator, microwave and coffeemaker a kitchen sink and induction burner to cook on. Also washer and dryer in the room. Upon your arrival there will be Banana Nut Bread, fruit & filtered water. All cotton sheets on the queen size bed (plus for the full size air mattress in room.) Cotton towels, shampoo, blow dryer, iron and ironing board.

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.

Cottage at Fruit Hill Orchard

The Cottage at Fruit Hill is nestled between our peach and apple orchards on my family’s 12 acre farm. Take a stroll through the peach blossoms, pick from our sunflower patch, enjoy some private time in the orchards during the fall, and gaze at our Christmas lights display in December. This charming cottage was originally built in the 1940’s and has recently been updated to be as comfortable for our guests as possible. Come enjoy a peaceful getaway at the orchard!

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).