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!

Spacious & Charming! Large deck+Game shed+Firepit

Get away and play at this spacious cabin. Sip your morning coffee on the large deck as the sun rises through the trees. By day, swim, explore nearby hiking trails, play tennis or golf at The Woods facilities, or lounge while the kids play in the fenced yard. As the sun sets, dine outdoors on the picnic table, or indoors on the large dining room table. At night, retire to the detached game shed for a nightcap or gather around the fire while you cherish the serenity and search the sky for Orion.

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.)

Starcatcher Chalet, The Woods Resort

Enjoy a fun, relaxing stay at our completely renovated chalet in The Woods Resort in beautiful Berkeley County, WV--a 90-minute drive from the Washington DC-Baltimore Metro Area. You'll be in the heart of the WV Eastern panhandle, close to Sleepy Creek, Berkeley Springs, Cacapon State Park, Antietam National Battlefield, and more. The Woods Resort amenities (fees apply) include a spa, restaurant, and two golf courses, three swimming pools, tennis, pickleball, fitness, and a playground.

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!

Five Oaks Cabin at The Woods Resort

Get away without going far at our cozy, colorful, family-friendly cabin. Watch the sunset over the woods from the deck, stargaze by the A-frame window, or play ping-pong in our games room. Do some work in our office space overlooking the trees. Enjoy golf, pools, the spa, hiking and fishing, or explore the beautiful countryside of rural West Virginia. Best of all, our cabin is less than two-hours drive from D.C. and Baltimore, so you can feel like you're far away without a long drive.

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

Getaway Sweet Zen Suite at Bryce Ski and Bike Park

Beautiful basement apartment with WiFi, parking and walking distance to Bryce Ski and Bike park (1.5 mile walk), trails (Lake Laura is 1/2 mile walk) restaurants and bars (1/2 mile to nearest; 1.5 miles to the resort). Short drive to breweries/wineries (Swover Creek, Woodstock Brewery, Cave Ridge ) Bryce security patrols the area regularly. Additional hiking and biking within short drives. Microwave, coffee pot, toaster, mini frig in the unit

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 Mountain Retreat w/ Amazing Views

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!

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.