Fitness-friendly holiday rentals in Madison County

The Cherry Tree, downtown estate, 8 parking spaces

Excellent downtown location & beautifully restored historic home within walking distance to the downtown mall, Main Street shops, and restaurants. Incredible attention to convenience details such as a wired conference room table, plumbed coffee machines, and a power strip next to every seat and bed. No need to compromise with small rooms or fight for bathrooms. Enjoy a bathroom to every bedroom and more than plenty of space, seating, and sleeping for 16 people. Come isolate in comfort and style.

Mountain Views, Game Room, Sauna, 3 Primary Suites

Discover the epitome of craftsmanship and luxury in this exquisite estate in Shenandoah Valley with magnificent views of Massanutten Mtn & Kennedy Peak. Three primary bedrooms with ensuites all on separate floors. Just minutes to Edinburg, National Forest & Parks, horseback riding, public river access, hiking, wineries/breweries, fly fishing, kayaking/rafting, canoeing, and offroad/ATV trails. Four-season resorts are 35 and 45 minutes away, with skiing/snowboarding, mountain biking, and more.

Rivanna Farm Estate North I Pickleball I Pool

This historic 42-acre country estate features four distinct residences, three of which are Airbnb rentals. The "North” offers beautiful views of the Blue Ridge Mountains and includes 4 bedrooms: 2 bedrooms with queen beds, and another with 2 twin beds on the main floor, and an additional queen bedroom upstairs. The second floor has a full kitchen, living room, & dining area. On the lower level is a yoga studio, game room, outdoor patio area w/seating, and charcoal bbq. (Charcoal not provided)

ONE MINUTE TO WINE HEAVEN ❤️ Hot tub ★ Home gym ★ Fire pit ★ Game Room ★ Private Footpath to Winery

Featured in Washingtonian Magazine, Fox Chase is nestled on five acres in the heart of Virginia’s wine country and is connected by a private footpath to Blue Valley Winery. Perfect for large groups, it is an ideal base from which to explore the vineyards, horse farms, history, hiking, and cycling routes of the Piedmont. Just four miles from Marshall, eight miles from Paris and Upperville, and 13 miles from Middleburg, the house is also close to some of the region’s finest shopping and dining.

Elmwood House

Find yourself surrounded by lush acreage & privacy in this fantastic home. Elmwood House is more than ready to assist in making the best memories with loved ones. You will feel as if you are secluded and away from it all. Step outside under the mature hardwoods and enjoy incredible views & the horses grazing. * We require honesty about your number of guests. Price is based on # of guests in accomodation* *Wifi- we care in the country and it is a hotspot- speeds vary* *We can house horses

Rustling Meadows Nest

Enjoy the peaceful surroundings of grassy rolling hills, magnificent hardwood forest, and riding trails for self-guided enjoyment. An inspiring children and dog friendly environment. Centrally located in the urban ring of historic Charlottesville/Albemarle County, enjoy the option of hoteling your horse at beautiful Rustling Meadows Stable with the best of comforts. 2 Bedrooms with Option of a 3rd Bedroom if desired for extra $48.00 per night. Third Bedroom has full bed w/ twin overhead.

ShenandoahEscape~HotTub~OutdoorCinema~DogFriendly

Why is Valley Crest Retreat a STEAL? Other 3BR houses with hot tubs cost $250+/night but they rarely come with so many extras! Your deal at Valley Crest Retreat is our Best Available Rate. You get an outdoor movie theater, fenced yard, EV charger, private hot tub, game room and hammock. We've even included complimentary firewood, s’mores kits, coffee/tea, sunscreen, insect repellent and more. And you can bring your dog! Rates vary by date – lock in prime weekends early for the best deal!

Cozy 1BD FULL PRIVATE APT in Charlottesville, VA

This is a full private apartment located in the lower level of a house in the Greenbrier neighborhood in the heart of Charlottesville, VA. It is self contained and includes a bedroom, living room, utility room, game room with pool table, darts and ping pong, small gym, and full kitchen and bath. 5 minutes from downtown and UVA. Under 5 minutes to JPJ, Amphitheater, downtown mall and Scott Stadium. Perfect for hiking, brewery and wine tastings, weddings, vacations, graduation, etc.!

Benji’s getaway Shenandoah. Pony rides for kids!

Named after my beloved son this little hideaway is the perfect spot for exploring all that this area has to offer. Apartment separate from main farmhouse but next to it, on 4 acres :) Please note this is a studio apartment so one room if you have more than two guests. There are horses, chickens and dogs on the property. Our pony ride business Benji’s Buckaroos does rides for young children! Wineries, hiking, breweries, antique shops, and our Mountain Views! Fire pit, Gas grill.

Walk to downtown - Cheerful Luray House!

Be close to everything when you stay at this centrally-located Main Street home, walking distance to Hawksbill Greenway trail, downtown coffee shops, restaurants, and art galleries. Our house is 13 minutes from Shenandoah National Park's Thornton Gap entrance and only 6 minutes from Luray Caverns. You will love sipping your morning coffee while lounging on the front porch's swinging chair and relaxing in our hotel-grade beds! Office area with fast wifi!

Massanutten Woodstone 2-BR, 2 Bath

I can offer you reduced prices on a week or two of vacation in a luxurious and spacious GOLD CROWN unit in a four seasons resort. All units have been recently remodeled in 2020, 2021 or 2022. You can expect a clean room that includes all the things you need in the kitchen and bathrooms. The resort has a mandatory $15.50 daily resort fee per unit payable upon check-in.

Relaxing Pet Friendly Home-Well Equipped-King Bed!

Step into Casa Massanutten, nestled within Massanutten Resort, where each season paints a new canvas of adventure! With 3 bedrooms, 2 baths, and pet-friendly vibes, it's your perfect getaway. Explore the resort activities, charming Harrisonburg, Shenandoah National Park, plus scenic trails and attractions. Don't miss out-Book now for family fun and relaxation!