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!

Peaceful Retreat on Creekside

Escape the hustle and bustle with this adorable farmhouse in a tranquil creek-side setting. Only couple miles off of I-81 yet it's secluded and will offer a great place to relax. Right on the creek where you can enjoy the sound of running water and birds chirping. This 2 bedroom house with a eat-in kitchen is perfect for a single family getaway or a small group of friends wanting to enjoy a serene vacation! Wineries and breweries close by to explore and Bryce Resort is about 25 minutes away!

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.

Modern Private Basement Suite

A private entrance basement apartment in our home in Montclair, VA. Minutes from I-95. Apartment is newly constructed as of October 2018. Locking door for privacy. Shared access to home gymnasium and washer/dryer combo. Entry and exit is through the garage, so you'll have no daily interaction with the hosts unless so desired. The space includes a brand new kitchenette, newly renovated modern private bathroom, new furniture, and new hardwood flooring. Wifi and Verizon cable are included.

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.

Stylish Retreat w Fireplace, Games & Pool Access

Experience a peaceful getaway at The Woods Resort. With an outdoor screened porch, a fire pit and a wood burning fireplace, you can comfortably enjoy this retreat in any season! Access to two outdoor pools, an indoor pool with hot tub, tennis and pickleball courts, a gym, and 36 holes of golf. Enjoy the indoors and outdoors in any season! The highlights: - Wood burning fireplace - Screened Porch with seating for the group - WiFi for streaming movies & remote work - Resort Amenities

Multi-Level Mountain Stay w/ Pool

Relax and recharge in this 2-bedroom multi-level condo at Chalet High, just 2 miles from Bryce Resort in Virginia’s scenic Shenandoah Valley. Featuring a full kitchen, fireplace, and private balcony, it’s ideal for families or couples seeking a cozy mountain escape. Enjoy access to an indoor pool, sauna, hot tub, and fitness center. Whether you're hiking, skiing, or simply unwinding, this peaceful retreat offers year-round comfort and convenience.

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.

One-bedroom apartment with separate entrance.

Adorable one-bedroom apartment with separate entrance. Located 10 minutes from downtown Chambersburg. Whether its historical sight-seeing, culturally diverse restaurants, or local craft beer, there is plenty to see and do in this area. Built in 2021, this apartment is on the lower level of our custom built home. It also has a fully equipped gym. Pet friendly, No smoking, No parties.