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!

Stonewall Abbey Apartment

This beautifully well lit contemporary apartment is located above Stonewall Abbey Wellness in vibrant downtown Sperryville. Private entrance leads you to a gorgeous apartment with a fully supplied kitchen, warm electric fireplace and outdoor eating area (small gas grill). The space is perfect for a couple or two friends to take in our local flavors, such as hiking, mountain/gravel biking, or catching up over beverages from our local breweries and wineries. We welcome pets: $50.00 pet deposit.

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.

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.

Charming Historic Frederick Home

Charming 1910 brick home with fenced yard located in the heart of Downtown Frederick, just steps to Frederick's best breweries, beautiful Carroll Creek, and the quaint shops at Everedy Square. The house is the perfect blend of old and new, combining exposed brick/stone, natural light and hardwood floors with modern amenities such as a remodeled kitchen, WiFi, central air, luxury mattresses and cozy furnishings. Family, work, and dog friendly ($50/stay fee; no dogs on furniture; max 2 dogs).

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!

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

Caprica (Private Ground Level Home)

Private Whole Lower Level. Caprica is the essential stay for an unforgettable Shenandoah Valley experience! Situated with perfect views of the outside, the guest quarters space is over 2200 sq ft. and features a lounge/media center, common meeting area, bedrooms & bathrooms, entertainment center with air hockey table and ping pong, and a fully supplied gym. See pictures for more details and information. Anyone is welcome to use the balcony, back patio, and fire pit.

Spacious Retreat for Groups, Well Stocked

Escape to our spacious group retreat for 12 in The Woods community! This home features multiple living areas, a detached game room, and a wraparound deck with a fire table. Enjoy resort amenities like pools, a hot tub, and a gym. Perfect for large families or groups seeking a comfortable getaway with plenty of space to relax and play. The unique layout ensures everyone has their own space, making it an ideal choice for a memorable gathering.