Holiday rentals in Wilderness

The Country House

✔ Peaceful setting with long private driveway ✔ Fire pit w/ string lights & Adirondack chairs ✔ Beautifully maintained outdoor spaces w/ front and back patios & charcoal grill ✔️Surrounded by mature-towering trees ✔ Fast Wi-Fi & easy check-in ✔ Convenient drive to Fredericksburg, Lake Anna, Spotsylvania battlefields & upcoming Kalahari water park Perfect for couples, solo travelers, small families/groups looking for a quiet, peaceful stay, a connection to nature and a short drive to everything

Hot Tub, Arcade, Golf, Pub, Beach: The Lucky Duck!

Unforgettable retreat with partial lake view, luxurious 7-person Jacuzzi, custom pub featuring a retro 4-player arcade with 7,500+ games and trackball, cozy woodstove, and delightful surprises! Ideal for epic family vacations, The Lucky Duck in the exclusive gated Lake of the Woods offers year-round fun—two lakes, eight pristine beaches, two pools, a golf course, an equestrian center, and scenic parks with fitness trails await! Come experience lakeside fun and relaxation! #TheLuckyDuckLOW

Cozy Farm Apt near Cville•wineries, mt. views

Come experience a relaxing getaway on our family’s dairy farm! Set in beautiful Orange County, We are close enough to Charlottesville (25 min) to fulfill all your shopping and eating needs, but have the privacy, calm and tranquility of the country, with beautiful majestic mountain views! This is a wonderful location for exploring all of wine country, unwinding from the hustle of busy life, and then taking in the sunset in this quiet country setting with rolling hills as your backdrop!

Lakefront at Turtle Cove

Enjoy the lake life in a peaceful quiet cove on the gorgeous large lake within Lake of the Woods. When not enjoying the newly renovated home with a vaulted ceiling great room, huge screened porch, and a desk and flat screen TV in each room, you can swim, float, kayak, or paddleboard in the quiet, secluded cove, or enjoy the 9 beaches or 2 community pools. Catch fish off the dock in one of the best fishing coves on the lake, and then warm up at night by the fire pit . Great for families.

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.

The Tobacco Barn

A high-peaked ceiling and exposed-log crossbeams reveal the Tobacco Barn’s past life as a place for hanging tobacco leaves to dry. Now converted to a one-room guest house, it features a front porch swing, cozy fireplace, soapstone floors, a homey sitting area, and a tall, high-post bed. The pressed-tin ceiling and whiskey-barrel sink in the bathroom add to its charm. Pets are allowed and are charged a fee of $25 (first night) and $15 (per ea. add'l night). Maximum two-person occupancy.

Stanley’s Cabin- Beautiful farm with private pond

Located at the foothills of the Blue Ridge Mountains in rural Culpeper County, Stanley’s Cabin sits on a private 7 acre pond surrounded by trees, open land, and grazing cattle. Ideal for couples, families, or small groups! Play a game of corn hole, fish for large mouth bass, take the kayak or canoe on the water, or just enjoy a peaceful walk. Many tourist attractions and activities are within proximity. Stanley’s Cabin awaits your next adventure or trip for rest and relaxation!

luxury couples retreat with HOT TUB!

This geodesic dome is more than a place to stay; it's an invitation to a world of intimacy and enchantment. It's designed exclusively for couples seeking a secluded and meaningful escape. Whether you're celebrating a special occasion or simply craving quality time together, our dome is the perfect setting. Has all you need King size bed, A/C, heating, luxurious bath, modern kitchenette, private outdoor space, hot tub, fire pit and grill all yours for an unforgettable ESCAPE!

Hidden Haven

Hidden Haven is just that! A 600 square foot romantic, private, peaceful, little haven. Hidden in the woods just 6 miles outside of the Town of Orange. Open the garage door in the living area and step out on the 300 square foot screened in porch where you can relax at the firepit under the covered roof. On the porch at Hidden Haven, we like to say, "time wasted is time well spent". The romantic vibe and modern amenities make it a prefect place for a couple's getaway.

c. 1830 Log Cabin Near Shenandoah National Park

Stay in a beautifully restored circa-1830 log cabin tucked into the forests of Virginia’s Piedmont near Shenandoah National Park. Crooked Tree Cabin blends historic charm with modern comfort, including central heat & AC and Starlink internet. Surrounded by wineries, Civil War history, and scenic countryside, the cabin offers a peaceful retreat for two. Located about 90 minutes from Washington D.C., it’s an easy countryside escape from the city.

Bond House: Historic Retreat at Walnut Grove

Escape from the city to a historic 1740s cottage with a distant view of the Blue Ridge Mountains and peaceful surroundings with the opportunity to experience the slower pace of country living. Spend the day at Lake Anna to swim/ kayak/ boat or visit the state park, just 5 minutes away. Enjoy local wineries, and explore historic Civil War battlefields. After a fun filled day, return to your private oasis with a fully equipped kitchen.

Life on the Lake, enjoy the peace and kayaks

Located within 20 minutes of both Fredericksburg and Culpeper, Virginia, this 2000 square foot home offers lakefront living on the 24-acre Keaton’s Lake within the gated community of Lake of the Woods. Keaton’s lake is ideal for fishing, swimming, kayaking or just lounging on the hammock or by the firepit enjoying the peaceful setting and beautiful view. Guests can also enjoy the 500 acre Main Lake and its beaches and parks.