Fitness-friendly vacation rentals in Winchester

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Top-rated fitness-friendly rentals in Winchester

Guests agree: these fitness-friendly rentals are highly rated for location, cleanliness, and more.

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Top guest favorite
A gravel area features several rustic wooden chairs arranged around a stone fire pit, with a gentle fire burning. Soft string lights illuminate the space, enhancing the cozy atmosphere. The exterior of the cabin is visible in the background, surrounded by trees.
Cabin in Hedgesville
4.95 out of 5 average rating, 168 reviews

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!

Top guest favorite
A contemporary living space features a living area with a gray sofa and a wooden coffee table, complemented by a side lamp. A dining table with place settings is positioned alongside an equipped kitchen, while a cozy rug ties the room together. Large windows allow natural light to fill the space.
Apartment in Sperryville
4.99 out of 5 average rating, 184 reviews

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.

Top guest favorite
The exterior of a rustic wooden chalet is showcased, framed by rolling lawns and lush trees. A picturesque sunset illuminates the sky, casting soft hues over the home. Multiple outdoor seating areas provide inviting spaces for leisure, blending harmoniously with the natural landscape.
Cabin in Fort Valley
4.98 out of 5 average rating, 101 reviews

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.

Top guest favorite
The open concept space features a comfortable seating area with a gray sofa, a large area rug, and a flat-screen TV mounted on the wall. A spacious king bed is seen alongside two bunk beds, all adorned with bicycles mounted on the walls.
Apartment in Oldtown
4.93 out of 5 average rating, 150 reviews

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.)

Guest favorite
The cabin features a contemporary A-frame design with large windows that reflect surrounding trees. A spacious deck wraps around the structure, providing outdoor seating options. Natural light streams through the windows, inviting a connection with the outdoors.
Cabin in Hedgesville
4.93 out of 5 average rating, 302 reviews

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.

Guest favorite
A spacious great room features a large sectional sofa in rich orange, inviting relaxation. Tall windows allow natural light to fill the space, offering views of the surrounding forest. A decorative area rug anchors the seating area, complemented by a coffee table and thoughtfully arranged decor.
Chalet in Hedgesville
4.94 out of 5 average rating, 181 reviews

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.

Top guest favorite
A scenic outdoor view showcases a wooden deck winding down to a lush landscape. Vibrant flowers and greenery adorn the space, while a hot tub is visible nearby. A beautiful sunset casts warm hues across the sky, offering panoramic views of the valley below.
Guest suite in Harpers Ferry
4.99 out of 5 average rating, 279 reviews

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.

Top guest favorite
Aerial view of a picturesque home surrounded by vibrant autumn foliage. Rolling hills are visible in the background, while the golden and orange leaves create a warm tapestry across the landscape, complemented by a tranquil sunset sky.
Home in Rileyville
4.95 out of 5 average rating, 150 reviews

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!

Top guest favorite
A rustic outdoor seating area features log benches arranged around a circular fire pit. The red chalet with a flag is visible in the background, surrounded by trees shedding their leaves. A gravel pathway connects the seating area and the chalet.
Chalet in Hedgesville
5 out of 5 average rating, 102 reviews

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!

Top guest favorite
The exterior of a red brick building is shown, featuring a striking peaked roof and multiple windows. A shaded porch is visible at the entrance, adorned with potted plants. Lush greenery surrounds the property, and a gravel path leads up to the structure.
Farm stay in Leesburg
5 out of 5 average rating, 105 reviews

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.

Top guest favorite
The living area displays a warm, inviting space with a plush sectional sofa and a round coffee table centered on a patterned rug. A wooden dining table is visible in the background, surrounded by chairs. Natural light enters through windows, enhancing the cozy atmosphere.
Cabin in Hedgesville
4.97 out of 5 average rating, 115 reviews

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.

Top guest favorite
A hanging chair is situated on a wooden deck, providing a comfortable spot for relaxation while enjoying panoramic views of the surrounding hills and valleys. The area is bordered by wooden railings, allowing for an open yet secure outdoor experience.
Home in Basye
4.99 out of 5 average rating, 261 reviews

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!

Popular amenities for Winchester fitness-friendly rentals

Quick stats about vacation rentals that are fitness-friendly in Winchester

  • Total vacation rentals

    Explore 20 vacation rentals in Winchester

  • Nightly prices starting at

    Winchester vacation rentals start at ﺩ.ﺇ477 per night before taxes and fees

  • Verified guest reviews

    Over 90 verified reviews to help you choose

  • Vacation rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Winchester vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Winchester rentals

  • 5 Average rating

    Winchester stays are highly rated by guests—averaging 5 out of 5!

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