Holiday houses in Woodridge

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.

Family · Location · Parking

Ultimate cabin in the mountains

This unique and secluded cabin sits on 75 acres in the Blue Ridge mountains. Enjoy the cozy wood fireplace, hot tub, charcoal grill, and fast, reliable fiberoptic internet if you need to get some work done while you're away. It has a washer and dryer, a full kitchen, and is pet-friendly (no pet fee!), so you can enjoy it with the whole family. There is a 4K 55” smart TV with apps, a Tesla LVL 2 charger, a cabinet full of board games, books, and plenty of items to entertain both kids and adults!

Value · Location · Amenities

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.

Location · Family · Pets

Shenandoah Stargazer with Sauna

Stargazer is the perfect place to get away from it all! The stillness and serenity of being nestled in a bird and wildlife sanctuary is so good for your soul. Watch the sunrise from a hanging basket chair at 2700 feet of elevation, or wait for moonrise and toast spectacular star views! Relax in the sauna after a day filled with hiking and an al fresco meal on the deck. Roast s’mores at the deck fire table or over the side yard fire pit. There's magic in the air at this mountaintop retreat!

Location · Family · Checkout

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.

Value · Family · TV

Unit 4 - Luxury King Suite with Private Balcony

Experience luxury and a unique journey through history at Sonsak - a newly renovated guesthouse in Albemarle County. Situated near the esteemed landmarks of Thomas Jefferson Parkway, Monticello, Ash Lawn and Michie Tavern, Ash, Sonsak is in a renowned area of historical significance. The property dates back to 1942 and has since been exquisitely renovated with lavish furnishings and modern amenities.Treat yourself to a stay at Sonsak and leave with lasting memories of comfort and beauty.

Location · Family · Accuracy

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.

Location · Value · Nearby

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.

Value · Location · Long stay

Small cozy Cabin in the foothills! Dogs welcome!

Escape to this private guest cabin for two in the rolling hills of Esmont, just outside Charlottesville and Virginia wine country. Set on 60+ acres of peaceful farm and woods, this quiet retreat offers privacy, wildlife, and open skies. Walk over two miles of private trails (when open) and unwind by the fire pit under the stars. Perfect for a romantic getaway or Blue Ridge escape. No cleaning fees—please tidy up. Dog friendly with a $50 NON-REFUNDABLE fee; dogs must

Value · Family · Breakfast

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.

Family · Value · Amenities

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!

Location · Family · Barbecue

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.

Family · Location · View