Holiday rentals in Wilderness

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Top-rated holiday rentals in Wilderness

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Top guest favourite
Cabin in Fredericksburg
4.97 out of 5 average rating, 33 reviews

Winter Little Stone Mill Historic Fredericksburg

Looking for the perfect cozy place for a little getaway? Book this unique one-of-a-kind charming replica of an Old Virginia Mill surrounded by a "little" river with a WORKING WATER WHEEL. It will transport you back to simpler times while offering all the luxury amenities & conveniences of the modern day! Traditional homestyle touches make for a truly comfortable & memorable trip. Located in the heart of a National Park & near historic sites, parks, rivers, lakes, wineries, restaurants & shopping

Top guest favourite
A cozy living room features a stone gas fireplace framed by elegant wooden details. Two black reclining chairs provide comfortable seating around a patterned area rug. Ambient lighting from decorative fixtures complements large windows that invite natural light into the space.
Cottage in Locust Grove
4.99 out of 5 average rating, 161 reviews

Quaint & Cozy LakeView Cottage - Lake of the Woods

Welcome to Brent and Carla's Lake View Cottage! Our beautifully renovated, fully furnished, unique and luxurious home is stocked with everything you need to enjoy your stay in beautiful Lake of the Woods. Our cozy cottage is a perfect get-away for your next vacation, visit with family, work trip, staycation or weekend getaway. You will instantly be set at ease as you enter our home featuring wonderful décor, detailed craftsmanship and lots of amenities to make your stay relaxing and memorable.

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, 279 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

Top guest favourite
A cozy living area is equipped with a vibrant yellow armchair and a light gray sectional sofa. A large screen TV is mounted on the wall, and natural light enters through a window adorned with white curtains. A round wooden coffee table sits on a patterned area rug.
Flat in Culpeper
4.98 out of 5 average rating, 123 reviews

Red Fox Retreat

Easily walkable to Downtown Culpeper! This restored and newly renovated historic property allows easy access to Downtown Culpeper. It features a large outdoor fire pit and expansive grounds to spread out and relax. This 1000 sqft unit is located in the upper level with views of the surrounding grounds and trees. Brightly decorated and designed in partnership with Lets Go and Stay properties; the Red Fox retreat is a great place to stay while visiting Culpeper and the surrounding area.

Top guest favourite
The exterior of the cabin features a rustic wooden facade with a steeply pitched roof and a welcoming front porch. A swing hangs from the porch ceiling, while the entry door is complemented by two symmetrical windows on either side, surrounded by natural greenery.
Cabin in Spotsylvania Courthouse
4.97 out of 5 average rating, 466 reviews

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.

Top guest favourite
The cabin features a welcoming front porch with a pair of white rocking chairs, providing a comfortable spot to relax. Wooden steps lead up to the porch, embraced by lush greenery and ferns, enhancing the cabin's secluded and natural setting.
Cabin in Culpeper
4.97 out of 5 average rating, 206 reviews

Comfortable and unique 1790's log cabin

Recently restored 1790's log cabin with modern amenities on a 30 acre horse farm. Secluded wooded setting with pond view, less than 1,000 feet from main house and only 5 miles from downtown Culpeper with it's fine dining and quaint shops. Take a short drive to scenic Shenandoah hiking & biking trails, local vineyards and distilleries, Civil War sites, Commonwealth Equestrian Park, stroll around the farm or just unwind on the front porch or in front of the wood stove with a good book.

Top guest favourite
A private cottage is nestled under a large tree, surrounded by well-kept grassy areas. The home features large windows that enhance natural light, with a welcoming entrance leading to a small staircase. The peaceful rural landscape extends in the background.
Farm stay in Warrenton
4.98 out of 5 average rating, 690 reviews

Winters Retreat Farm Cottage - Entire house

Need a change of view? Unplug, and relax in this independent private cottage on the homestead. Watch for deer, turkeys and birds in the field from the sunroom or take a hike around the farm. Centered in Fauquier's wine country it is ideal for the weekend escape, or day trips West to the mountains, East to DC or points south. Also, a perfect solution for accommodating family at get-to-gathers, wedding guest, or your "Halfway overnight stay" traveler North/ South or to the beach.

Top guest favourite
This historic brick building features a balanced façade with multiple windows and a gabled roof. The structure is complemented by surrounding trees and a parking area. Parked cars line the street, indicating an accessible location in a bustling downtown area.
Apartment in Fredericksburg
4.95 out of 5 average rating, 285 reviews

Casa 1776 - Spacious Apartment | Heart of Downtown

Rest in the heart of downtown Fredericksburg! You’ll stay in the lower level apartment of this historic home. Constructed during the Revolution, and used as a hospital during the Civil War, this home is directly across from the visitor center, within steps of landmarks, awesome restaurants, taprooms, and shops. It’s the perfect spot for a weekend away or historic excursion. The newly constructed River Front Park sits at the rear of the property and is awesome for the little ones.

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, 151 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
The spacious studio features a white, wooden bed with dark blue bedding, complemented by a bedside table and lamp. A kitchenette is visible, along with a dining area set for two. Light pours in through sliding glass doors, leading to a small outdoor area.
Guest suite in Fredericksburg
4.99 out of 5 average rating, 338 reviews

Spacious studio apartment - The Inn at Dewberry

The Inn at Dewberry. Our roomy studio apartment is located in a quiet friendly neighborhood just 4 miles from downtown historic Fredericksburg. For traveling medical personnel, Mary Washington Hospital is less than 4 miles away. Our area is rich in Civil War history with lots of great places to dine, shop, or catch a Fredericksburg National game at the ballpark. Close to I95 for a trip to Washington, DC (60 mi) or south to Richmond. Kitchenette but no stove. Microwave.

Top guest favourite
A modern studio space features large windows that allow natural light to fill the room. A cozy yellow chair sits beside a small coffee table, with a guitar resting on a stand nearby. The bed area is visible in the background, framed by a stylish shelf.
Guest house in Boston
4.99 out of 5 average rating, 217 reviews

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.

Superhost
A modern kitchen features warm wood cabinetry and granite countertops. Stainless steel appliances, including a refrigerator and microwave, are visible. Two bar stools are set at the kitchen island, which provides additional seating. Soft lighting illuminates the space, highlighting the tile flooring.
Flat in Locust Grove
5 out of 5 average rating, 6 reviews

Feel Completely at Home 3

Luxurious, furnished basement with a private entrance, granite kitchen & bath. Cute as a button and worth every penny! Close to shopping in a beautiful and very quiet neighborhood with walking trails. Kitchen, living & dining rooms; breakfast nook; washer & dryer. Driveway parking. I am seeking a single (as in one (1) person) professional individual with a day shift job. You must be clean & neat. You won't be disappointed! PLEASE READ THE HOUSE RULES.

Popular amenities for Wilderness holiday rentals