Fitness-friendly holiday rentals in Winchester

Modern Cabin: Hot Tub, Arcade, FirePit, Pets+Pool

Experience the epitome of luxury in our breathtaking A-frame cabin, nestled amidst the serene woods. This modern retreat offers lavish amenities and a stunning open living space with floor-to-ceiling windows, immersing you in nature's beauty. Indulge in the private hot tub, relax by the fire pit, and unleash your culinary skills in our fully equipped kitchen. The large screened porch provides a tranquil oasis, while nearby hiking trails, golf courses, and a spa offer an unforgettable getaway!

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.

Oldtown Schoolhouse. C&O Canal Lock 70.

The space is an open concept classroom inside of an old school 500 yards from the C&0 Canal Lock 70. Guests of Lock 70 Schoolhouse enjoy the entire space of this open concept which includes 1 King Bed, 2 Bunk Beds, and a fully stocked coffee bar area with a microwave, water cooler and refrigerator and internet. A private bathroom with a hot shower awaits after your long day on the trail. Also housed in the school is a restaurant and a small store (owned by a separate party, closed on Mondays.)

Bear Pines Retreat ~ Game Room ~ Screened Porch

Come enjoy this 3 bedroom/2 bath A frame cabin in The Woods. Bear Pines Retreat features 2 bedrooms on the lower level with 4 beds and full bathroom. The Master Suite loft has a queen bed with mountain spa bathroom. You can connect to the built in Bluetooth speaker and play some relaxing music while looking out the skylight above. The living area has plenty of seating with wood burning fireplace and 55” TV mounted above. You can enjoy over 100 cable channels, music and streaming services.

Luxury Mountain Getaway: Sunsets, Wines & Views

Celebrate your special moment in chic elegance and 5-star amenities for adult couples only. You deserve the Sunset Rouge. It's a destination in a relaxed and romantic setting to escape anxiety of kids, city, and work. Let the fun décor and panoramic views inspire the writer and artist within. During the day, take flight with eagles at eye level. At night, gaze into the heavens to catch a falling star. Within 2 miles is Lake Shannondale with beach access provided by the Mountain Lake Club.

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!

Cherry Run Chalet

Kick back and relax in this peaceful, stylish chalet at The Woods community in wild and wonderful West Virginia. The 2-acre property backs up to the 23,000-acre Sleepy Creek State Wildlife Area, a hikers dream. The Woods offers 2 golf courses, indoor and outdoor pools, indoor hot tub, tennis, exercise gym and more. The Sports and Spa center is within walking distance from the chalet for self-care pampering. The Clubhouse Grille and Pub is a great option for dine in and carry out. Enjoy!

The Forge on Sunnyside Farm

Sunnyside Farm offers a luxurious stay in a beautifully restored historic forge. You’ll be greeted by the farm’s delightful hosts, Jimmy and Dean, two friendly Potbelly pigs. Beautiful cows forage right outside your door. The Forge features exposed wooden beams, brick walls, and cozy furnishings. The interior is designed with plush bedding, a fully equipped kitchen, and spacious living reminiscent of yesteryear. Breweries, wineries and famous antique stores nearby offer entertainment.

Mountain views, Sunsets, Hot Tub & Fire Pit!

**Please note this guest suite is entirely private and located on the lower level of our home, with its own entry/exit and no shared areas.** We block Monday & Tuesday nights, but will entertain requests if you would like to book. The hot tub is a new feature on the property. It is located on the lower deck. Guests who utilize the hot tub do so at their own risk. In order to ensure your safety and for our protection, no one under the age of 12 is permitted to enter/use the hot tub.

Whitetail Summit - Shenandoah/hot tub/wineries

Whitetail Summit is a spacious chalet with stunning mountain views, river access, and hiking on property. You'll have close proximity to 30+ wineries/breweries, the Shenandoah National Park, the Appalachian Trail, the Shenandoah River, horseback riding, and hunting preserves. Or relax at home, with an indoor pool/ping pong table, music nook, outdoor hot tub, and fire pit. We are family/pet-friendly. REMOTE WORK: 600MBps wifi, two dedicated work-from-home spaces, and a GYM/PELOTON

Cedar Loft at The Woods-Vintage Chic Cabin Retreat

Located just two hours from Washington, DC and Baltimore, MD, this 3 br-1ba cabin is nestled in the Appalachian Mountains of Almost Heaven West Virginia. One of the few properties at The Woods that backs directly to Sleepy Creek Wildlife Management Area, this cabin was completely renovated in 2020, including the addition of granite countertops, all new flooring, a metal roof, new appliances and new decking.

Bryce Resort Cabin | Amazing Views | Sleeps 10

Discover the perfect mountain retreat at Bryce Resort! Our award winning home offers breathtaking mountain views, a 5-minute walk to ski lifts, and a short drive to golf, hiking, and Lake Laura. With 5 bedrooms, 3 baths, a large fireplace, 2 spacious decks, and high-speed WiFi, it’s ideal for families, groups, and remote work. Enjoy skiing, biking, kayaking, or lounging by the fire—book your stay today!