Holiday rentals in Wilderness

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Top-rated holiday rentals in Wilderness

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Top guest favourite
Farm stay in Elkwood
4.99 out of 5 average rating, 144 reviews

The Garden View Suite—Zero In Hidden Fees!

Private luxury. This serene guest suite is situated on a 43-acre farm--Bees & Trees--and is attached to the North end of the main farmhouse. A private garden-gate takes you straight to your suite just steps from the pool. Enjoy a magical sky full of stars while relaxing in the hot tub or enjoying the fireplace! There are breathtaking sunrise views from your front windows, gorgeous sunsets from your back porch and the nearby gazebo gives you both views. You owe yourself a stay with us!

Guest favourite
A well-equipped kitchen features white cabinetry and a spacious countertop. Stainless steel pots hang above the gas stove, while a microwave and dishwasher are visible. Natural light is provided by overhead lighting, highlighting the organized kitchen tools and appliances.
Flat in Fredericksburg
4.86 out of 5 average rating, 289 reviews

Cozy Entire Apt Designer Kitchen 4 miles from Expo

SUMMARY Guest love our cozy, comfortable smoke free property 2 bedroom. Sorry no pets allowed. Close to historic Fredericksburg and restaurants, Expo Convention Center in a quiet neighborhood. You’ll love the proximity to Civil War Historic Parks. Enjoy a comfy queen bed and crib in one bedroom and a double bed with twin bed above and with a pull out second twin bed if needed in the second bedroom. Proximity to DC, Richmond, King's Dominion, and Shenandoah. One night stays ok Sunday -Thur

Guest favourite
A welcoming house is set amidst tall trees, showcasing a pathway leading to a front entryway. Large windows invite natural light, while the surrounding greenery highlights the property. The serene lakeside environment is enhanced by well-maintained landscaping.
Home in Locust Grove
4.81 out of 5 average rating, 53 reviews

Harrison Hideaway

Introducing Harrison Hideaway, a peaceful family friendly lake front getaway at Lake of the Woods! The full renovation of this lake front home is now complete & is available for rent to family groups. Our house features 5 bedrooms, 3 full baths, a sunroom, a great room with kitchen, dining/family room with lake views & a lower level rec room with ping pong table. You can also charge your electric car in the carport with our level 2 charger. We also have a canoe, kayak and paddle boards.

Top guest favourite
A charming green cottage is presented, featuring a small front porch with two chairs and potted flowers. Large windows allow natural light to fill the space, while the surrounding landscape includes grassy areas and trees, providing a peaceful rural setting.
Bungalow in Orange
4.99 out of 5 average rating, 469 reviews

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.

Top guest favourite
Guest suite in Fredericksburg
4.98 out of 5 average rating, 248 reviews

Downtown Oasis (Pets Welcome)

Our warmly decorated guest suite is attached to but fully separate from the main part of our home, with its own private entrance. The suite includes a spacious bedroom, large bathroom and separate living/sleeping area with a TV, mini-fridge/freezer, microwave, and Keurig. An adjacent laundry room is available for your use upon request (FOC). The small deck, patio and fully fenced yard are included for your exclusive use. Parking is available on the street right out front of our home.

Guest favourite
A calm pond is viewed from the foreground, reflecting a blue sky with clouds. Lush greenery surrounds the water, with a dock visible in the distance. The scene conveys a sense of tranquility, highlighted by the still surface and natural surroundings.
Cabin in Culpeper
4.95 out of 5 average rating, 136 reviews

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!

Superhost
A spacious bed is adorned with a heart made of towels and surrounded by red rose petals. Red throw pillows with romantic phrases are positioned against the headboard, adding a touch of intimacy to the setting.
Dome in Unionville
4.84 out of 5 average rating, 172 reviews

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!

Top guest favourite
The living area features a dark leather sectional sofa and a light grey armchair, arranged around a round black coffee table. A large flat-screen TV is mounted on the wall, and sliding glass doors provide access to the outside. Decor includes a circular patterned rug.
Flat in Fredericksburg
4.98 out of 5 average rating, 156 reviews

Stay Awhile

“Stay Awhile” is a spacious walk out basement apartment in our home, very clean, in a quiet neighborhood minutes from Old Town Fredericksburg, University of Mary Washington, Fredericksburg Convention Center, FredNats baseball stadium, restaurants, shopping, historical sights, battlefields & Heritage Trail along the Rappahannock River. We have a walk/run/bike trail in our neighborhood and a tandem bike you may borrow. Enjoy our 82” TV and WIFI. We are 1 hr from DC & Richmond

Top guest favourite
A modern cabin-style home is nestled among tall trees, showcasing a sleek black exterior. A spacious screened-in porch is visible, supported by a deck with steps leading down to a gravel path. Large windows enhance the connection with the natural surroundings.
Home in Orange
4.98 out of 5 average rating, 177 reviews

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.

Top guest favourite
A charming historic cottage is featured, showcasing a white exterior with a red metal roof. The front porch is framed by a small staircase and surrounded by well-maintained greenery. Tall trees provide shade on the side, set against a backdrop of an expansive blue sky.
Cottage in Spotsylvania Courthouse
4.89 out of 5 average rating, 182 reviews

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.

Top guest favourite
A wooden dock extends over the lake, featuring two green adirondack chairs overlooking the water. Two kayaks, one blue and one black, rest on the shore, alongside smooth rocks and a planter with greenery.
Home in Locust Grove
4.97 out of 5 average rating, 66 reviews

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.

Top guest favourite
The cabin features a rustic log exterior with a steel roof, framed by trees displaying autumn foliage. A welcoming entrance is highlighted by a wooden door and two windows with green trim. Benches are positioned on the front porch, offering a comfortable outdoor seating area.
Cabin in Spotsylvania Courthouse
4.97 out of 5 average rating, 269 reviews

The Bedford Cabin

A gorgeous chink-style log cabin boasting a wood-burning fireplace, kitchenette, living room, and private patio. If you are looking for serenity and privacy in a rustic setting, this cabin is for you! This cabin is NOT pet-friendly. Take advantage of our walking trails that wind through hundreds of yards of Civil War earthworks!

Popular amenities for Wilderness holiday rentals