
Holiday rentals in Wilderness
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Top-rated holiday rentals in Wilderness
Guests agree: these stays are highly rated for location, cleanliness and more.

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

Hummingbird Lakehouse
Hummingbird Lakehouse in Locus Grove, VA, offers waterfront access to the lake and various outdoor activities like golfing, kayaking, swimming, fishing, and horseback riding. Guests can gather around the fire pit and access community amenities like the pool and beaches. Nearby historic sites & hiking trails provide additional exploration opportunities. If you're looking for a peaceful getaway or an adventure-filled vacation, this lake house offers an idyllic setting for making lasting memories.

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.

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.

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!

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

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.

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.

Mountain Cabin Getaway w/WiFi, TV, Fire Pit, Patio
This unique, modern cabin is located only minutes from Old Rag Mountain, White Oak Canyon, trout fishing, horseback riding, wineries, breweries, and more! This 400 sq ft. tiny home has all the modern amenities you need to feel right at home. Step outside and relax on your private patio with a cozy fire and s’mores. Are your desired dates already booked? Check out our other listing, Black Bear Cabin!

Lake House | Outdoor Chimney | Gazebo & Dock
★☆ ABOUT THIS SPACE ☆★ Discover our lakeside retreat directly on Lake Wilderness. Enjoy indoor comfort with a cozy living room and well-equipped kitchen. Outside, embrace nature on the deck, in the gazebo, the dock, or by the lakefront chimney. Kayaking, fishing, and ample parking add to the adventure. Welcome to your waterfront escape.
Popular amenities for Wilderness holiday rentals
Other great holiday rentals in Wilderness

Private Retreat Near Lake Anna & Local Wineries!

*Spring Fun*|4BR Lakefront|Fireplace| Firepit|BBQ

The House on Stoney Creek Drive!

Lakefront retreat with huge screened-in porch

Riverfront* Views* Balcony* King-2* BBQ* Peaceful

Wilderness Resort- Hot tub Rancher

Cabin’ A Good Time- Lake Front Property

Sauna & Game Room: Lake House in Locust Grove!
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Long Island Holiday rentals
- Western North Carolina Holiday rentals
- Washington Holiday rentals
- East River Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Pocono Mountains Holiday rentals
- Charlotte Holiday rentals
- Shenandoah National Park
- Kings Dominion
- Luray Caverns
- National Harbor
- Early Mountain Winery
- University of Virginia
- Downtown Mall
- Lake Anna State Park
- James Monroe's Highland
- Prince Michel Winery
- Tysons Corner Center
- George Mason University
- John Paul Jones Arena
- Monticello
- Jiffy Lube Live
- Glass House Winery
- Maryland International Raceway
- Sky Meadows State Park
- Shenandoah River Outfitters
- The Rotunda
- Ingleside Vineyards
- White Lotus Eco Spa Retreat
- Mosaic District
- Cooter's Place




