Holiday houses in Lake Monticello

Small cozy Cabin in the foothills! Dogs welcome!

Peace and tranquility is what you will find in this guest cabin for two nestled in the rolling hills of Esmont. The 60+ acre farm is teeming with wildlife. Spend your morning walking over two miles of private trails (when open) throughout the property and enjoy evenings sitting around the fire pit. Hate cleaning fees? Us too, so we've decided to eliminate it for our rentals-just please clean up after yourselves. Dog friendly with a $50 NON-REFUNDABLE fee. Dog must be noted on your reservation.

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.

Cozy cabin for 2 w/mountain views & trails

Cozy cabin in the woods with beautiful mountain views from covered back deck! Perfect for nature lovers, couples, singles. Ideal for a peaceful escape or visiting local wine/brew trail. While remote, also a convenient base to visit area attractions, hikes & easy drive to C'ville. Relax on the covered back deck watching the sunset and wildlife. Over 2 miles of wooded trails on property for guest use. 15-20 min walk through woods trails (part of this walk is on a hill) to access Rockfish River.

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.

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.

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.

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).

Luxury tiny house 3 min from UVA

La Casita is a new tiny home combining modern luxury with central location adjacent to UVA, central to wineries, and 10 minutes from Monticello. La Casita is design built to offer custom furnishings and luxurious touches. We are in the residential pedestrian-friendly neighborhood of Fry's Spring, near I 64. Walk to restaurants and Scott Stadium. Enjoy all amenities including a high-speed internet.