Vacation rentals in Madison County

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Top-rated vacation rentals in Madison County

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
A modern yurt is showcased with a domed roof and wooden exterior, surrounded by a green lawn. The large windows offer views of the landscape, while a spacious porch extends around the front. Autumn foliage adds color to the background.
Cabin in Syria
4.96 out of 5 average rating, 314 reviews

⭐️Mongolian Yurt⭐️1100ft²⭐️Fire Pit⭐️Full Kitchen

Modern day interpretation of Mongolian yurt with view of Blue Ridge Mountains and the Rose River Valley • 17ft (5m) domed living room ceiling • Fire pit (wood supplied) • Fully equipped kitchen • Extremely safe neighborhood • Onsite, secured parking for 4 vehicles • 1,100ft² / 100m² • 50 inch Smart TV with satellite connection and movie channels . No cleaning fee or extra charges Note: High speed satellite WIFI is complimentary, though it can be impacted by weather. Follow us @roseriverfarm

Guest favorite
An aerial view captures the surrounding countryside, featuring sprawling green fields and distant mountains under a partly cloudy sky. The image shows a mix of residential buildings, including cottages and a red-roofed structure, situated amidst lush trees.
Cottage in Madison
4.91 out of 5 average rating, 172 reviews

Robinson River Roost - Cottage near Shenandoah NP

Enjoy a slice of country life in our rustic 2 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.

Top guest favorite
A hot tub is positioned on a wooden deck, overlooking a scenic valley and distant mountains. The sky is filled with vibrant hues of orange and purple as the sun sets, creating a tranquil ambiance in this outdoor space.
Cabin in Stanley
4.99 out of 5 average rating, 276 reviews

New, 5BD/4BA | hot tub, arcade, pool table, views

Welcome to this new, 2,880 sf LUXE retreat in Shenandoah Woods--a spacious cabin designed for unforgettable getaways. It features 5 king beds, 4 full baths (2 en suite, 1 adjoining, 1 hall), and stunning views from the porches, hot tub, and rooms. More highlights: ★Arcade, board games, 6 ft pool table ★Fire pit ★Elect fireplace ★Elect Grill on deck ★Smart TVs up to 70" ★Fast WiFi ★Dining for 10 ★Well-equipped kitchen ★5 mins-Stanley ★13-15 mins-Luray Caverns ★25 mins-Shenandoah National Park

Top guest favorite
Guest suite in Reva
4.97 out of 5 average rating, 154 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
Home in Madison
4.96 out of 5 average rating, 183 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.

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
4.97 out of 5 average rating, 128 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 charming cabin with light-colored wood siding is set against a snowy landscape. A welcoming wreath adorns the front door. The surrounding area features tall trees blanketed in white snow, with steps leading up to the porch where a rocking chair is placed.
Home in Montpelier Station
4.93 out of 5 average rating, 555 reviews

The Cottage At Liberty Mill Upgraded WI FI Pet $50

Brand new charming cabin with views of the Blue Ridge Mountains. Two bedrooms, Loft with 2 twin beds, two large bathrooms and a spacious common area. Exposed chestnut beams, working gas fireplace make this cabin a perfect getaway. All the amenities you could want. Located minutes from James Madisons' Montpelier, 5 minutes from Historic Orange, 30 minutes to Charlottesville, 20 minutes to Culpeper and less than 2 hours to Washington, DC. A loft area with 2 twin beds. Upgraded WIFI

Guest favorite
A rustic cabin sits atop a rocky incline, surrounded by tall trees that reach towards the cloudy sky. The structure features a sloped roof with exposed wooden beams and a deck extending towards the front, providing an inviting space to enjoy nature.
Farm stay in Brightwood
4.94 out of 5 average rating, 163 reviews

Robinson River Cabin - Tri Creek Farm

If you spend most of your career glued to a computer and other screens, this place is for you. TriCreek Farm is a place for you to disconnect, reboot, and fuel your soul. This riverfront cabin is situated on ~100 acres, over 1/2 mile of Robinson River frontage, with breathtaking views. There are creeks, fishing, and hiking trails to explore and enjoy. The cabin is located in Brightwood, Virginia, a small town located in Madison County between Culpeper and Charlottesville Virginia.

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
4.93 out of 5 average rating, 177 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
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, 472 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! 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.

Top guest favorite
Guesthouse in Boston
4.97 out of 5 average rating, 233 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.

Top guest favorite
The exterior of a two-story cottage is visible, featuring a welcoming porch. Large windows allow for natural light, and seating is arranged on the porch. Surrounding greenery and a gravel pathway add to the peaceful ambiance, with a gently sloped landscape in the background.
Barn in Boston
5 out of 5 average rating, 126 reviews

Pet Friendly Cottage on 21 acre farm

Enjoy the lovely, quiet setting on 21 acres. Newly renovated 2 story bank barn will be your home away from home. Soft, muted colors, zen feel. Come relax, hike, ride your bike, go wine and craft beer tasting, Copper Fox Distillery, has nice gin and bourbon if you prefer. Visit Luray Caverns and Shenandoah National Park, or shop at Sperryville gift shops, restaurants, antique markets and art galleries. Old Rag Mountain is only 20 minutes away!

Popular amenities for Madison County vacation rentals