
Holiday rentals with outdoor seating in Madison County
Find and book unique Holiday Houses with Outdoor Seating on Airbnb
Top-rated Holiday Houses with Outdoor Seating in Madison County
Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.

⭐️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
Outdoor spacesLocationView

Mountain Cabin Getaway 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
LocationOutdoor spacesWalkability

Log Cabin at 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.
ValueOutdoor spacesAccess

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.
LocationOutdoor spacesSleep quality

Countryside getaway 5 min. from Old Rag parking!
Just 5 min away from Old Rag trailhead in Shenandoah National Park and merely minutes from wineries/breweries. Our guest house is close to White Oak Canyon, Skyline Drive, Three Blacksmiths, Washington, and Luray Caverns! Book here if you like: -Escaping the hustle and bustle, and relaxing in nature -Hearing birds sing while sipping coffee/tea/wine on the porch -Observing wildlife (including our chickens and bees) -Fishing on the Hughes River in our backyard -Stargazing and spotting fireflies
LocationOutdoor spacesSleep quality

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.
ValueOutdoor spacesDecor

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!
LocationValueParks

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.
LocationValueParking

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.
Outdoor spacesValueTV

Red Gate Cabin: Hike into Shenandoah National Park
A true local gem, Red Gate Cabin is a one-of-a-kind, secluded, luxury cabin adjoining the Shenandoah National Park. You can hike directly from the cabin to the Appalachian Trail, Big Meadows, and Skyline Drive. At the cabin you will find modern amenities, including an EV charger, spacious outdoor decks, rocking chairs, smart TVs, a firepit, and much more! At 1,800 feet in elevation the air is cooler in the summer and views are spectacular year-round including the stars at night!
ValueLocationView

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.
ValueLocationHospitality

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.
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Popular amenities for Madison County outdoor seating rentals
Holiday House Rentals with Outdoor Seating

Monrovia on Main
Outdoor spacesValueNearby

Atlast-The Farmhouse
LocationOutdoor spacesWi-Fi

Unit A-Mountain Retreat- SAUNA-Hiking-Wineries
ValueLocationWi-Fi

Robinson River Retreat - Near River, SNP & Graves
Outdoor spacesLocationBathroom

Enchanted-Historic Shenandoah Farm
Outdoor spacesLocationTV

Firnew Cottage
ValueLocationBeach

Family Getaway at Cross Mountain
ValueOutdoor spacesFamily

Modern Farmhouse near Shenandoah Nat'l Park + Lake
Outdoor spacesLocationCheckout
Apartment rentals with outdoor seating

1 Bedroom Apartment With a Kitchenette on 28 Acres
Outdoor spacesLocationShared spaces

Couples' Cozy Gettaway in Orange Va
LocationHospitalityIndoor spaces

The Apartment at Dark Run Retreat
LocationValueQuiet

come and stay at bird song hill
LocationOutdoor spacesParking

The Studio at Dark Run Retreat
LocationValueBathroom

Spacious Upstairs Apartment on beautiful grounds
Outdoor spacesLocationCheck-in
Other holiday rentals with outdoor seating

Stay near Old Rag +White Oak Canyon—Cozy Log Cabin
LocationValueAccess

10-Acre Dog-Friendly House w Grill & Near Wineries
LocationOutdoor spacesCleanliness

The Cabin at the Lake
Outdoor spacesLocationComfort

Private Fenced Yard for Dogs/Horses - 2BR Cottage
LocationOutdoor spacesHospitality

Farm Cottage just outside town of Orange.
Outdoor spacesValueWi-Fi

Madison Farmette Guest House
LocationOutdoor spacesCleanliness

Spectacular Mountain Retreat
LocationValueCondition

Comfy Cottage Near SNP, Hiking, & Wineries
Outdoor spacesValueWi-Fi
Destinations to explore
- Family-friendly rentals Madison County
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- Rentals with a fire pit Madison County
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- Rentals with a fireplace Madison County
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- Bed and breakfasts Madison County
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- Rentals with a washing machine and dryer Madison County
- Pet-friendly rentals Madison County
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- Cottage rentals Madison County
- Rentals with a kayak Madison County
- Rentals with outdoor seating Virginia
- Rentals with outdoor seating United States
- Shenandoah National Park
- Luray Caverns
- Lake Anna State Park
- Bryce Resort
- University of Virginia
- Early Mountain Winery
- Jiffy Lube Live
- James Madison University
- Monticello
- Glass House Winery
- Blenheim Vineyards
- Cardinal Point Winery
- Prince Michel Winery
- Shenandoah River Outfitters
- The Rotunda
- John Paul Jones Arena
- Frontier Culture Museum
- James Monroe's Highland
- Downtown Mall
- Sky Meadows State Park
- Shenandoah Caverns
- Grand Caverns
- White Oak Lavender Farm & The Purple WOLF Vineyard
- IX Art Park





