Fitness-friendly vacation 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.

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.

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.

Shenandoah Escape: Hot Tub, Outdoor Movies & Dogs

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.

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

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!

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!