
Fitness-friendly vacation rentals in Winchester
Find and book unique fitness-friendly rentals on Airbnb
Top-rated fitness-friendly rentals in Winchester
Guests agree: these fitness-friendly rentals are highly rated for location, cleanliness, and more.

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!

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.

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.

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!

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.

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

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!

Steinbeck/Fitzgerald Cabin at Buffalo Gap Retreat
DECK EXTENSION ADDED - This comfortably rustic, large double cabin is great for larger groups. It is well appointed with a kitchenette, full bathroom - including shower, WIFI, outdoor area with firepit, picnic table and charcoal grill. It is a great spot to enjoy and access all that Buffalo Gap Retreat has to offer. Our newly added deck allows for a comfortable area to lounge and take in the surrounding beauty.
Popular amenities for Winchester fitness-friendly rentals
Fitness-friendly apartment rentals

Peaceful Riverfront Retreat w/ Yoga & Art Studio!

Lovely One bedroom apartment with pool

Adjustable Head & Legs Firm Mattress King Bed.

King Size Bed - Reston Metro Apt

The Manhattan

Grand-Lux | Pool & Gym | Free-Parking

Modern 1 bed/1 bath in Reston VA

Affordable Suites Quantico - Near Marine Corp Base
Fitness-friendly condo rentals

2 Bdm Condo @ Massanutten Woodstone Meadows Resort

Massanutten Woodstone Apartment Units, 2BR & 2BA

Massanutten Woodstone 2-BR, 2 Bath

Luxury 2BR 2BA w Hot Tub bath at Massanutten

Regal getaway at Massanutten Resort

2bed/2Bath at Massanutten

Woodstone at Massanutten 2br suite, Sunday check-i

Massanutten 4 seasons resort 1br1ba Hottub in room
Fitness-friendly house rentals

Mountain View Cabin with Hot Tub, The Blue Spruce

New ShannondaleRetrear near Lake:Hot Tub&Play Room

Mountain DesignerHome•Waterpark&Golf•Sauna&Firepit

Makin' Mountain Memories Jacuzzi, Fire pit, Grill

Peaceful Retreat on Creekside

Beautiful, rustic/unique home near Gettysburg!

More Luxury = Gym + Entertainment + Best Location

Romantic Cottage with Private Hot Tub
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 G$35,555 GYD per night before taxes and fees

Verified guest reviews
Over 10 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
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- Fitness-friendly rentals Virginia
- Fitness-friendly rentals United States
- Luray Caverns
- Stone Tower Winery
- Bryce Resort
- Berkeley Springs State Park
- Cunningham Falls State Park
- Cacapon Resort State Park
- Whitetail Resort
- South Mountain State Park
- Jiffy Lube Live
- Harpers Ferry National Historical Park
- Shenandoah River Outfitters
- Green Ridge State Forest
- Reston Town Center
- Rock Gap State Park
- Hollywood Casino At Charles Town Races
- Antietam National Battlefield
- Sky Meadows State Park
- Skyline Caverns
- Dulles Town Center
- Bluemont Vineyard
- Museum of the Shenandoah Valley
- Weinberg Center for the Arts
- Old Town Winchester Walking Mall
- Greenbrier State Park





