Holiday rentals in Wilderness

Historic 1830 Cabin Near Shenandoah National Park

Nestled in Virginia’s Piedmont near Shenandoah National Park, this restored c.1830 log cabin offers a peaceful romantic escape for two. Crooked Tree Cabin blends historic charm with modern comfort, including central heat/AC and high-speed Starlink internet for remote work or streaming. Surrounded by vineyards, Civil War sites, hiking, and scenic countryside drives, it’s ideal for Virginia wine country and outdoor exploration. Just 90 minutes from Washington, DC, it’s an easy countryside getaway.

Luxury Apartment in Downtown Culpeper

Stay in the heart of downtown Culpeper in this luxury suite. Featuring a beautiful King bed, large bathroom and an amazing overlook of Davis Street, this second story apartment features a soaking tub, fireplace and a gorgeous view of the downtown. Walk down the stairs and directly into all of the restaurants, shopping and breweries within a one minute walk. You won't find another space like it. The suite has a shared entryway with one other suite (also available on Airbnb) but is very private.

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

The Adrian Cabin

This quaint log cabin tucked back in the woods of Stevenson Ridge is your perfect sanctuary from your bustling home life. With a private patio amid Virginia’s nature and wildlife, you will feel the weight lift off your shoulders as you relax and enjoy a glass of local Virginia wine or read up on our famous Civil War History. Two-person maximum occupancy. Additional roll-away bed may be added for $20/night. Pets are allowed and are charged a fee of $25 (first night) and $15 (per ea. add'l night).

Cabin Sweet Cabin

Relax with the whole family at this peaceful rustic resort getaway! D.C., Richmond, Lake Anna, Colonial Beach, Fredericksburg battlefields, Kings Dominion, and the Raceway are all just a short drive away for vacationing fun! OR stay & play at the cabin with the hot tub, walking trails, firepit, outdoor games, bumper pool, arcade games, connect 4 hoops, theater room, and lots of places to relax! Boat & RV parking available. A little bug spray recommended. Other amenities are available (ask us!).

Lakefront Retreat | Hot Tub • EV Charger • Gazebo

⭐ ABOUT THIS SPACE ⭐ Escape to your own private lakefront retreat on Wilderness Run Lake. Wake up to peaceful water views, spend your day kayaking or fishing right from the dock, and unwind in the hot tub surrounded by trees as the sun sets. 🌿 WHAT MAKES THIS PLACE SPECIAL 🌊 Direct lake access with private dock and kayaks 🛁 Secluded hot tub 🌳 Gazebo for enjoying nature and flat top grill for breakfast 🔥 Outdoor chimney by the lake 🔌 EV charger on-site (perfect for Tesla & EV travelers)

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.

Beachwalk Hideaway

Escape to our delightful Beachwalk Hideaway, a cozy retreat that offers easy access to the serene beach on the shimmering lake. Walk just 6 houses down to Ramsey Beach for sandy shores on the lake. Lounge by Ramsey Beach water's edge, build sandcastles, swim, and immerse yourself in the calm of lakeside living. As evening falls, enjoy breathtaking sunsets and starlit skies from your piece of paradise. Book your stay now and experience the ultimate in lakeside relaxation and recreation.

Spacious Shenandoah Home on 35 Private Acres

Sitting on 35 acres of private land to be explored, this classic countryside vacation rental ticks all the boxes for a relaxing outdoors-geared getaway! You can practically picture yourself enjoying a glass of wine after a long day of exploring the natural beauty of Virginia from this perched hillside home, sporting a long private drive, and an expansive furnished deck. This 2-bed, 2.5-bath outdoors oasis is sure to have everyone unplugged, outside and enjoying living in the moment.

Cozy Farmhouse Getaway

Life is good on the farm! Our charming three-bedroom guest house offers a true home-away-from-home experience, where rolling fields, open skies, and friendly cows are your closest neighbors. Enjoy breathtaking sunrises and sunsets in a peaceful countryside setting, just 11 miles from downtown Culpeper. You’ll be close to numerous wineries, breweries, and historic sites, with easy day trips to the Shenandoah Mountains, Lake Anna, Fredericksburg, Charlottesville, and Washington, DC.

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!

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.