Vacation rentals in Wolftown

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Top-rated vacation rentals in Wolftown

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Superhost

A wooden cabin with dark siding is positioned amidst greenery, surrounded by trees. A deck extends from one side, providing outdoor space. Large windows invite natural light into the interior, visible through the windows. A gravel path leads to the entrance, enhancing accessibility.

Home in Madison

4.94 out of 5 average rating, 118 reviews

Designer cabin in the woods at Shennadoah NP

Come relax at our scandi inspired cabin in the woods. Five acres of pristine woods are the perfect backdrop for our renovated house, making it an ideal weekend retreat away from the busy city life. Discover the best spots in the area, including wineries and breweries, caverns and trails, antique shops and local makers, only a few miles from the house. Whether you are looking for a restful getaway, a source of inspiration, or a place to stay while you discover Virginia, this is the place for you.

Guest favorite

A living area features a dark leather armchair and a black sofa adorned with decorative pillows. A round coffee table sits on a patterned rug, while a floor lamp provides soft lighting. Large windows offer a view of the surrounding nature.

Cottage in Hood

4.95 out of 5 average rating, 114 reviews

The Cozy Conway Cottage

Enjoy peace and quiet along the Conway River. This relaxing getaway is about 1/4 mile off of rte 230. The cottage was an original one-room cabin with a centrally located wood stove/fireplace. It now boasts 2 bedrooms, 1 bathroom, a full kitchen, large windows and a patio/deck with river views. During the fall and winter months, you can see the sunset over the mountains of the National park. It’s a 20 min drive to the Shenandoah National Park entrance and 5 minutes from Early Mountain Vineyard.

Top guest favorite

A luxury tiny cottage is showcased amidst a lush green landscape, with a curved outdoor sauna adjacent to the home. The gravel pathway leads to a spacious deck with steps, while expansive views of rolling hills and trees form the backdrop, complementing the serene setting.

Tiny home in Madison

5 out of 5 average rating, 142 reviews

Luxury Tiny Home 2: Sauna, Farm & Mountain Views

The retreat at Rooted Land Co. consists of 1 farmhouse and 3 luxury tiny cottages on 350 private acres nestled at the base of the Blue Ridge Mountains with more than 1-mile of Rapidan River frontage. Each home is spaced with privacy in mind and positioned with breathtaking views. Countless outdoor activities including fishing, hiking, and wildlife viewing provide a unique experience during your stay. Rooted Land Co. is located just minutes from wineries, breweries, and Shenandoah National Park.

Top guest favorite

Lush green shrubs form a natural foreground against rolling hills. A distant mountain is partially shrouded in mist, while blue skies are visible above. Farm buildings are seen in the background, nestled among the trees and fields.

Chalet in Hood

4.99 out of 5 average rating, 281 reviews

Firnew Studio

Romantic getaway from the city in the heart of Virginia Wine Country, 15 minutes to Shenandoah National Park, 30 minutes to Charlottesville. Private art studio on 265 acre farm with spectacular Blue Ridge views. Deck overlooks pond. Perfect sunrise and sunset viewing. Walk to swimming hole, collect fresh eggs, feed goats, canoe in pond or simply relax on large private deck. Perfect for one couple. Close to wineries, breweries, hiking, Montpelier, Monticello. 1.5 hrs from DC/ Richmond.

Top guest favorite

A round green yurt nestled among trees displays a welcoming entrance with wooden steps leading to its door. Lush foliage surrounds the structure, adding a natural backdrop. Sunlight filters through the branches, highlighting the peaceful setting of the retreat.

Yurt in Stanardsville

4.95 out of 5 average rating, 1,226 reviews

Yurt*POOLpeace*FARM*horses*goats*woods*STARS*Hotub

Come experience living in a round structure filled with amenities-fully equipped kitchen, deep tub, heating and AC, hot tub and in ground pool. Great for couples, friends, and families. A 10 minute hike gets you into Shenandoah National Park, explore our 58 acres on numerous walking trails, visit Charlottesville, historical sites, caves, or play in rivers. Child friendly- no pets. Private hot tub Labor Day-Memorial Day. Check out Cair Paravel Farmstead on FB/the web to see all we have to offer

Guest favorite

A charming cottage is framed by lush greenery, with a covered porch extending across the front. Colorful flowering bushes add vibrancy to the landscape, which features well-maintained garden beds and a birdbath. The cottage is situated on a grassy area that leads to a secluded wooded backdrop.

Guesthouse in Syria

4.96 out of 5 average rating, 396 reviews

Little House on Strother Run

Nestled between Mount Tom and Double Top Mountain and at the edge of the Shenandoah National Forest, Little House is the perfect starting out and ending point for a peaceful and relaxing stay in the Appalachian Mountains. Little House is located at the edge of our 7 acre property. You'll enjoy the bucolic atmosphere of our farmette which includes use of our shared sitting area on Strother Run. The sitting area is shared with the main house which is rented or used by our family periodically.

Guest favorite

The kitchen features modern cabinetry and a central wooden island with high stools. A large window allows natural light to fill the space, complemented by stylish pendant lighting. Appliances include a black refrigerator, stove, and sink, creating a functional and inviting area for meal preparation.

Cottage in Madison

4.92 out of 5 average rating, 147 reviews

Creekside Cottage Near Hiking

Creekside Cottage is the perfect getaway home to escape to the beautiful Blue Ridge Mountains. This newly renovated luxury cottage is only minutes from hiking trails and just a short drive from the Old Rag trailhead. Nestled in Syria, Virginia, this comfortable space features updated amenities such as a rain shower, a well appointed kitchen, plenty of lounge spaces, board games for days, and a central wood burning stove. Just a few steps out the back door you'll find your own private creek.

Top guest favorite

A rustic log cabin is surrounded by lush greenery in a serene wooded setting. The spacious front lawn is fenced, providing a safe area for pets. The porch features a swing, inviting relaxation amidst the natural landscape.

Cabin in Madison

4.96 out of 5 average rating, 102 reviews

Relaxing 2BR CABIN, 12 acres, dog friendly, hiking

Bring the whole fur family & enjoy precious time away from the hustle & bustle of everyday life. This updated cabin sits on 12.5 acres of mainly wooded land in the heart of the blue ridge- Madison County. Within 30 minutes of wineries, breweries, hiking, & Charlottesville! Boasting a primary loft bedroom w/ a queen bed and a bonus room w/ a full bed, this home away from home can comfortably sleep 4-5! Front porch swing & fenced yard for the pups to play. Guests can completely relax!

Guest favorite

A welcoming entrance to the duplex is highlighted by a stone pathway leading to a wooden porch. Lush greenery surrounds the porch, with shrubs and trees providing a serene atmosphere. The sky is partially cloudy, adding to the tranquil outdoor setting.

Home in Madison

4.95 out of 5 average rating, 429 reviews

Unit A-Mountain Retreat- SAUNA-Hiking-Wineries

Renovated duplex in Madison, VA. Enjoy a peaceful setting, amazing views and convenient to wineries, wedding venues & hiking. SAUNA! On-site walking trail. Near Early Mtn Vineyards, Prince Michelle Winery, Yoder's Market, Bald Top Brewing & Plow & Hearth. A 30 min drive to Charlottesville, Shenandoah Nat. Park, Culpeper & Orange. Shopping, restaurants, breweries, antiquing, site seeing and more. *RENT ENTIRE HOME* - Inquire for our unit A & B combined rate. Dogs allowed-$30 fee.

Guest favorite

A charming guest cottage is nestled among lush green landscaping. The structure features a metal roof and a porch with simple white railings. Tall trees provide shade, contributing to the serene atmosphere of the surrounding countryside.

Cottage in Madison

4.92 out of 5 average rating, 165 reviews

Charming Guest Cottage at Winery

Early Mountain Vineyards' charming Guest Cottage, nestled next to our front block of grapevines and below our historic hilltop barn, offers breath-taking views of the Blue Ridge Mountains and a serene place to watch the sunset while sipping wine. Only short distance to our Tasting Room - open 5 days a week, Thursday - Monday. We recommend a reservation in advance - this can be made via our website, Early Mountain Vineyards, or by calling our winery directly.

Top guest favorite

The cabin exterior is surrounded by lush greenery, with a spacious covered porch featuring a wooden railing. Planters with flowers are visible at the front, while a well-maintained lawn leads to the entrance. A small outbuilding is located nearby among the trees.

Cabin in Stanardsville

5 out of 5 average rating, 120 reviews

Conway Cabin

Conway Cabin is an old hunting cabin that we have made into a comfortable and relaxing getaway. It is located at the foot of Lewis Mountain part of the Shenandoah Nation Park. National Hiking trails just up the road and Early Mountain Winery and Bald Top Brewery are 15 minutes away. Go out enjoy your day and come back and relax in the Conway River or on the large covered porch. STARTING SEPTEMBER 2025 FIREFLY WIFI WILL BE AVAILABLE AT CONWAY CABIN

Superhost

A small, rustic cabin is set amidst a lush green landscape, framed by trees. The cabin features a front porch with a green door and a chimney, surrounded by a well-maintained grassy area. Natural light filters through the foliage, creating a serene atmosphere.

Guesthouse in Syria

4.87 out of 5 average rating, 667 reviews

Cozy 1 room cabin in the mountains.

In the heart of the Shenandoah mountains. 1 mile from White Oak Canyon and Old Rag for amazing hikes. Perfect for the fly fisherman (lots of local streams) or a nice quiet get-away for a couple. Once you park your car you can sit back and just listen to the river flowing in the back yard & enjoy a nice beverage next to the fire pit. The property is a very special place! UPDATE: New kitchen counters and new table and chairs