
Holiday rentals in Wilderness
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Top-rated holiday rentals in Wilderness
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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!

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

The Farmer's Cottage at Kings Crossing
Keep it simple at this peaceful and centrally-located home. The Farmer's Cottage at Kings Crossing is a newly renovated and tastefully furnished three bedroom/two bathroom home. Its unique charm captures a modern farmhouse feel, next to the heart of historic Fredericksburg! King's Crossing is nestled between downtown Fredericksburg and the battlefields; you will find that getting to local attractions is an easy drive. Additionally, we are within 1 hour of DC, Richmond, and Shenandoah.

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.

The Skyhouse- simple & serene w/mountain views
Enjoy the solace and beauty of the Blue Ridge Mountains with modern and local comforts. Retreat and explore on this old 100acre farm- via foot- or float on the tiny pond in a kayak or SUP. Or venture out to Shenandoah National Park, the local coffee shops, eateries, wineries, and breweries. Whatever you choose the skyhouse is stocked with roasted coffee, farm-fresh eggs, fresh-baked bread, teas and soaps from our incredible local homesteaders and artisans.

Apartment, centrally located Historic DnTwnFXBG!
Welcome to downtown Fredericksburg's historic district! This charming 1st-floor apartment (~500 sqft) sleeps up to 4 with a modern-boho vibe. Enjoy a full kitchen, spacious living & dining area, and a large TV for unwinding. Steps from Caroline Street's shops, restaurants, and galleries — no car needed! Self check-in via smart lock makes arrival easy. Perfect for couples, small families, or a solo getaway in one of Virginia's most walkable historic towns.

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.
Popular amenities for Wilderness holiday rentals
Other great holiday rentals in Wilderness

Horse farm near wineries, breweries, and history.

Tiny Home on an Animal Farm

Private Retreat Near Lake Anna & Local Wineries!

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

Lakefront retreat with huge screened-in porch

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

Mount Hope

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
- East River Holiday rentals
- Washington 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
- John Paul Jones Arena
- George Mason University
- Monticello
- Glass House Winery
- Jiffy Lube Live
- Maryland International Raceway
- Shenandoah River Outfitters
- Sky Meadows State Park
- The Rotunda
- Ingleside Vineyards
- White Lotus Eco Spa Retreat
- Cooter's Place
- Mosaic District




