Holiday houses in Madison

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Top-rated holiday rentals in Madison

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Guest favourite

Apartment in Madison

4.9 out of 5 average rating, 230 reviews

The Studio at Dark Run Retreat

Quiet studio on a secluded 5 acres only 3 miles from town. Kick back and relax by the pool in the warmer months, or in the hot tub in the cooler months. Small trails lead to the creek running along the property, maybe you'll even catch a glimpse of the deer or turkey that wander thru...we've even seen a lil bear once! There is an apartment above the studio, so we ask that you be mindful of those guests if occupied. *The studio got a make-over! As of 10/6/20, we will no longer be hosting pets*

Guest favourite

Cottage in Madison

4.91 out of 5 average rating, 142 reviews

Robinson River Roost - Cottage near Shenandoah NP

Enjoy a slice of country life in our rustic 3 BR, 1.5 bath cottage nestled along the Blue Ridge in Madison County. Great for a family or small group. Minutes to scenic hikes at White Oak and Old Rag in Shenandoah National Park, plus wineries, breweries and festivals at Graves Mountain Lodge. Steps away from trout fishing and swimming holes of the peaceful Robinson River, plus Possum's Store across the street. Convenient to Charlottesville, Culpeper, Blue Ridge Pkwy, Luray Caverns, Camp Varsity.

Guest favourite

Farm stay in Madison

5.0 out of 5 average rating, 204 reviews

Rustic Farmhouse on Farm W/ Mountain & River 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.

Guest favourite

Cottage in Madison

4.98 out of 5 average rating, 130 reviews

Fishback Cottage, Central location

Conveniently located in beautiful countryside of Madison, VA. With easy access to route 29 and centrally located to local breweries, wineries and hiking. Free fast wifi makes it easy for a business trip or for a night of relaxation with Netflix. Local places to visit include Bald Top Brewing Company, Early Mountain Vineyards, Prince Michel Vineyard, Yoder's Country Market, Piedmont Deli, Shenandoah National Park and Graves Mtn Farms. An easy 25-30 minute drive to Charlottesville or Culpeper.

Guest favourite

Home in Madison

4.96 out of 5 average rating, 350 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. New 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. Pet (dogs only) $30 per night.

Guest favourite

Guesthouse in Syria

4.95 out of 5 average rating, 335 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 favourite

Guest suite in Culpeper

4.98 out of 5 average rating, 255 reviews

Spacious property-deluxe amenities; hot tub & more

Enjoy the beauty of nature in our beautiful private 2 room suite. Located in Culpeper County Virginia, you are minutes away from world class dining, wineries, great breweries while only 20 minutes from Shenandoah National Park. Retreat to the deck for an evening soak in the hot tub after a day of exploring the area. This space provides a queen bed, plenty of sitting space, full private bathroom, walk in closet, 50 inch smart TV, WIFI, mini fridge, ice maker, microwave, and coffee maker.

Guest favourite

Guest suite in Ruckersville

4.98 out of 5 average rating, 137 reviews

Serenity Lakeview Cottage

Renovated lakefront apartment, downstairs from the main home. It is located on beautiful Greene Mountain Lake with year-round lake and mountain views. Wildlife on the lake includes geese, herons, ducks, osprey, eagles, turtles, and beavers. The setting is serene and peaceful. You will have a private entrance and a covered porch. Pedal kayaks are available (with short training) for your use on the lake. Unit approved with a Special Use Permit for Tourist Lodging by Greene County.

Guest favourite

Yurt in Etlan

4.95 out of 5 average rating, 195 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 favourite

Cottage in Ruckersville

4.91 out of 5 average rating, 269 reviews

Lake Haven Cottage

Make yourself at home at our peaceful 1-bedroom cottage that has everything you need for your trip to the Blue Ridge Mountains. The cottage comes with heating, AC, Washer+Dryer and DIRECTV. During your stay, you can also enjoy using a convenient private bathroom, kitchen, and living room. Our Airbnb is within driving distance to UVA, the Skyline Drive & Shenandoah National Park, local wineries, craft breweries and much more!

Guest favourite

Chalet in Brightwood

4.97 out of 5 average rating, 108 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

Guest favourite

Guesthouse in Madison

4.97 out of 5 average rating, 230 reviews

Hebron Valley Cottage

Nestled in the scenic Hebron Valley, this 2 bedroom 1 bath cottage is the perfect getaway from busy, city life. The cottage offers panoramic views of the Blue Ridge Mountains, including Old Rag and is located near several wineries, breweries, restaurants, antique shops, hiking trails and historic sites. The cottage is 3 miles from the town of Madison and is convenient to Charlottesville, Culpeper and Orange.