Vacation rentals in Madison County

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Top-rated vacation rentals in Madison County

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Superhost

Home in Madison

4.94 out of 5 average rating, 117 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.

Top guest favorite

Cabin in Etlan

4.99 out of 5 average rating, 154 reviews

Modern Mountain Cabin w/WiFi, TV, Fire Pit,Patio

Come escape to our cozy retreat amidst the stunning beauty of the Shenandoah National Park region. Our unique 400 sq ft tiny home offers all the modern amenities, fully equipped kitchen, private patio w/ fire pit, loft bedroom , and spacious bathroom. Only minutes from Old Rag Mountain, wineries, breweries, horseback riding, trout fishing, and more. Unwind & relax after a day of exploring on your spacious patio.Are your desired dates already booked? Check out our other listing, Bald Eagle Cabin.

Top guest favorite

Tiny home in Madison

5 out of 5 average rating, 135 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

Cabin in Madison

5 out of 5 average rating, 153 reviews

Log Cabin and Ragged Rock Ridge

Mountaintop log cabin nestled in a mature, tranquil forest with spectacular views, ideally located near adventures like hiking in Shenandoah National Park (including Old Rag & White Oak Canyon), many local wineries/breweries/distilleries and quaint towns of Sperryville & Madison, VA. The authentic log cabin includes a cozy stone fireplace, porch, and patio with Old Rag views. Ponds, wildlife and hiking also available on the sprawling 300-acre property. Escape to the Cabin at Ragged Rock Ridge.

Top guest favorite

Guest suite in Reva

4.96 out of 5 average rating, 124 reviews

The Log Cabin at Ridgeview - Hiking, Wine, UVA

Entire main floor of quaint log cabin in the heart of Virginia's Wine Country. Close to Charlottesville airport, UVa campus, Shenandoah National Park, wineries, breweries, local restaurants. NOTE: Prices shown are for 2 bedrooms, 1 queen and 1 double, and 2 baths. For access to 3rd bedroom, at an additional fee which includes one double and one single, set number of guests to 5 or 6. Access to laundry. Cozy front porch, tons of parking, screened in porch out back for dining or relaxing.

Top guest favorite

Guesthouse in Syria

4.96 out of 5 average rating, 394 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

Yurt in Etlan

4.96 out of 5 average rating, 235 reviews

Peaceful Secluded Old Rag Retreat

The spacious one bedroom yurt is located high on a forested hillside in the middle of 15+ acres. Come enjoy a natural and serene getaway with all the comforts of home- a full kitchen (ie, all utensils, setting for four), a bathroom with shower and laundry, a queen bedroom, and a queen foldout sofa in the living room by the wood burning stove. The windows roll up from the outside and have permanent screens inside. There is also a BBQ grill, a separate firepit, and WiFi via satellite.

Guest favorite

Home in Madison

4.96 out of 5 average rating, 163 reviews

Spacious Shenandoah Home on 35 Private Acres

Sitting on 35 acres of private land to be explored, this classic countryside vacation rental ticks all the boxes for a relaxing outdoors-geared getaway! You can practically picture yourself enjoying a glass of wine after a long day of exploring the natural beauty of Virginia from this perched hillside home, sporting a long private drive, and an expansive furnished deck. This 2-bed, 2.5-bath outdoors oasis is sure to have everyone unplugged, outside and enjoying living in the moment.

Superhost

Cottage in Madison

4.92 out of 5 average rating, 164 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

Guesthouse in Boston

4.98 out of 5 average rating, 199 reviews

The Bunkhouse- 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 bunkhouse is stocked with roasted coffee, farm-fresh eggs, fresh-baked bread, teas and soaps from our incredible local homesteaders and artisans.

Guest favorite

Cabin in Pratts

4.97 out of 5 average rating, 147 reviews

Stunning Modern Cabin w WiFi near Shenandoah Park

My family lovingly restored this log cabin and it was recently featured in the Washingtonian as one of the top places to visit in the DC region! We’re so excited to share it with you! It is one of the only houses in the area with reliable high speed xfinity wifi. It is a short drive to so many of the popular Shenandoah National Park hikes and it's centrally located to so many of the popular breweries, wineries, restaurants, and adorable small towns.

Guest favorite

Chalet in Brightwood

4.97 out of 5 average rating, 150 reviews

Charming Chalet in Blue Ridge Wine Country

NEW! PICKLEBALL/BASKETBALL COURT PUTT PUTT GOLF Sunset Ridge is in the heart of all you want to do! Newlyweds to families, everyone will love it here! The peace and quiet of the country, or the excitement of exploring new and different places, all await you! Check out our guidebook for local attractions, restaurants, nightlife, and sightseeing. Enjoy the serenity of the country! Follow us: @sunsetridgechalet