Winchester Holiday Rentals
Holiday Rentals in Winchester
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.
Family Farmhouse Inn
Cabin w Hot Tub, Indoor Pool / Gym Access, & Grill
Dreamtime - Modern A-frame Cabin w/ Hot tub
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River
Cozy Mountain Cabin w/ Steam Shower. Family Friendly!
Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo
Riverfront Farmhouse with Mountain Views, Hot Tub, Fireplace, Screen Porch, WIFI
Cozy Lakeside Homestead
❤️ Secluded 1940s Romantic Tiny House on the River
"Solitude" Secluded 1 BR Cabin w/ Hot Tub near Luray, VA.
Escape to Shenandoah River, Hot Tub after a Hike!
Secluded, Cozy Cottage in the Shenandoah Valley
Hidden Gem in the woods with hot tub
Riverside cottage, minutes from historic Harpers Ferry; private river access!
Breathtaking views with an indoor private pool, come escape with us
Cottage w Hot Tub, Pond & Kayaks, Fire Pit, & WiFi
Above The Rivers Edge Cabin #1
Other types of properties in Winchester you may be interested in
La Quinta Inn & Suites by Wyndham Winchester
Microtel Inn & Suites by Wyndham Winchester
Travelodge by Wyndham Winchester
You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Winchester holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.
As much as you love your vacation rental, it’s always good to get out and explore to soak up Winchester. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Winchester. Seeing all the best attractions is bound to make you fall in love with Winchester. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.
It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Winchester short-term rentals, that won’t be hard to do.
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