Kid-friendly holiday rentals in Madison County

New~5BD/4BA~Upscale~Arcade~LL

★New LUXE cabin, new build, A+ views, 2880 sf ★5 king bedrooms, 4 full baths (2 en suite, 1 adjoining, 1 hall) ★In Shenandoah Woods ★Arcade & board games, books, 6 ft pool table ★Porches & hot tub overlooking valley & mountains ★Fire pit ★Electric outdoor grill ★Fireplace (elect.) ★Smart TVs (incl. a 70") ★Fast WiFi ★Dining for up to 10 people (with extension) ★Firewood provided for fire pit ★Well-equipped kitchen ★5 mins-Stanley ★13-15 mins-Luray/Luray Caverns ★25 mins-Shenandoah National Park

The Conway House

Get away on the Conway, a place to recharge, relax and explore. Located just outside a back entrance to the Shenandoah national park. Walk, run, or bike these lightly traveled country roads to access the trail heads. This private cottage is the ideal location for visiting the Shenandoah national park, hiking, fishing, biking, wineries, and getting away to relax. This newly remodeled mountain retreat is updated with modern decor and all the essentials for an unforgettable mountain getaway.

Willie's Place Country Cottage Pets Allowed

Step out your front door and pet horses located next door. Willie's place is newly renovated and has all the amenities you need. Located close to wineries, shopping, wedding venues, Historic Montpelier, Corn Maze, Town of Orange, Woodberry Forest School, 10 minutes to Gordonsville, 30 minutes to Charlottesville. Kayak the Rapidan, take a horseback ride at Oakland Heights or see a play at Barboursville. Exposed beams throughout, a beautiful Loft and back porch for sitting. You won't go wrong.

The Tool Shed, Pet Friendly

The Tool Shed at Mountain Field Farm provides a delightful retreat just a short 20-minute drive from the majestic Old Rag Mountain and the serene White Oak Falls. Immerse yourself in the breathtaking landscape, explore the nearby exquisite wineries and craft breweries, and meander through the quaint streets of Culpeper, where adventure blends seamlessly with relaxation and fine dining. Don’t forget to bring along some peppermints for our gentle horses, who are always eager to greet visitors.

Creekside Cottage at Shenandoah

Welcome to our secluded cottage in the woods overlooking Shenandoah National Park! Your home base is located 10 mins from the cute town of Luray, through idyllic farmland and on acres of private hillside forest along a relaxing creek. As you enter this 3br/2ba home, you’ll find cozy cottage charm with thoughtful updates and modern amenities complete with a private hot tub. Within ~20 mins you'll find: - Shenandoah NP entrance - Luray Caverns - Wine country - Canoeing the Shenandoah River

Serendipity with a View. (cozy mountain retreat)

If you want relax with a quiet mountain view. WE HAVE STARLINK WIFI. Very little to no cell sevice. Serendipity is perfect place to reconnect with a family, group of friends, or romantic getaway ( Fire place inside, games, books) Fabulous view is Graves Mountain. Great hiking with the famous Whiteoak Canyon Trail and Old Rag Mountain Trail, just to name a few. Lots of local wineries to explore. Robinson River steps away for great trout fishing. Private pond access .25 away.

Charming Carrie's Cottage at Fairhill Farm

Carrie's Cottage is nestled in a private corner of our Fairhill Farm. Delight in the bold views of the Blue Ridge Mountains. Hike private trails on our 150 acres. Fish in pond or river. Enjoy pool. Delight in farm animals including our miniature horses. Located 2 hours southwest of Washington, DC, 1 1/2 hours east of Richmond and 25 minutes north of Charlottesville, VA. Near wineries; Shenandoah National Park and AP; Monticello, Montpelier, Ash Lawn, and UVA

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.

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