Holiday houses in Lake Monticello

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.

Bluebird Cottage B: Quiet, Firepit, Patio, Games

You’ll enjoy the simple charms of this home for up to 4 guests conveniently located near Lake Monticello, Charlottesville, the Rivanna River, and wineries. Relax in peace in a quiet neighborhood. Enjoy your private patio with outdoor dining table. Play board games, cornhole, and horseshoes. Make memories around the firepit. You’ll have everything you need, including fully equipped kitchen, washer-dryer, electric fireplace, fast Wi-Fi, 2 smart TVs for streaming services w/antenna for local fare.

Mountain Overlook House - Blue Ridge Parkway

Unique octagonal house with stunning views of the Blue Ridge Mountains of Virginia. Located 2 miles from I-64, 15 minutes to downtown Waynesboro and an easy 25 min drive to Charlottesville and UVA. Open floor plan, perfect for gathering, and long-range 180 degree views from nearly every room. Fully equipped renovated kitchen. Quality linens and bedding. Rustic, yet modern decor. Home features large fireplace, outside fire pit, wifi, and board games galore. Stargazing and birdwatching heaven.

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.

Luxury Cottage | Outdoor Tub + Mountain Views

Soak in a private outdoor bathtub beneath the stars, wake to mountain views from your king bed, and open an entire wall of glass to bring the Blue Ridge Mountains inside. Welcome to The Cottage at Perkins Hollow Retreat! Located in Nelson County, just minutes from the Nelson 151 Brew Trail, award-winning wineries, breweries, hiking, and only 25 minutes from Charlottesville, The Cottage is the perfect destination for a romantic getaway, anniversary, honeymoon, or peaceful retreat.

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.

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.

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!

CloudPointe Retreat

Rare Appalachian Treehouse Gem! Luxurious, one-of-a-kind retreat for couples. Elevated tiny house among the treetops, private parking, plush bedroom, sleek bathroom, beautiful kitchenette, loveseat, lounge, private double-level decks, fireside lounging (wood provided), gas grill, and patio with a hot tub! Surrounded by nature, with wineries, hikes, restaurants and shopping all nearby. Please come and relax and revel in the beauty of nature! 4WD is recommended.

Cozy Wine Country Escape | Near Clifton Inn

Tucked in Keswick, Virginia, this renovated 2-bedroom, 850 sq/ft suite is your perfect wine country escape. Two queen bedrooms, full kitchen, living room, and private entrance — all your own. Less than a quarter mile from Clifton Inn, minutes from Keswick Hall, and surrounded by award-winning wineries. Downtown Charlottesville is 15 min away, Monticello just 7. When the day winds down, find your spot in the hammock under the trees.

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).