Holiday Rentals in Winchester
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Holiday Rentals in Winchester

Canal Cabins

Private, light filled retreat space... with your own pickleball court!

Dreamtime - Modern A-frame Cabin w/ Hot tub

Log Cabin w Loft, Hot Tub, Deck, Fire Pit, & WiFi

Secluded River Cabin Getaway (Masten Cabin)

Charming Cabin in the Woods with River Access

Cozy Bear Cottage! Hot Tub! Tranquility! Unlimited Wifi!

"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA

"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub

Outdoor Theatre | Hot Tub | Fire Pit | Dogs

Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly

Star view cabin-Riverfront

Family Farmhouse Inn

Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!

Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo

Grill, Fire Pit, WiFi, Deck, Hammock, Games & Dogs

Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub

Bear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal (hottub)<br>
Other types of properties in Winchester you may be interested in

La Quinta Inn & Suites by Wyndham Winchester
Holiday Accommodation Winchester
You’re the type of person who wants to be right in the middle of it all, but still have your own space. You want to be able to take care of everything yourself, but also get plenty of R&R. Well, holiday rentals in Winchester are ready to roll out the welcome mat. We mean that literally—they probably do have a welcome mat. It’s all those little things that will make you fall in love with this type of accommodation, and with Winchester itself. Once you’ve stayed in a holiday rental, you’ll wonder why you ever stayed anywhere else.
Winchester holiday houses have everything you could need in a place to stay, along with several things you probably never even thought you needed. Towels and linens? Check. Cooking utensils? Check. Dog treats for the pupper? Well, you might want to bring your own to your pet-friendly holiday house, just in case. (He’s a picky little prince anyway, right?) But otherwise you’re good to go. You might even find some games for the little ones, if you’re bringing the family along.
If you are bringing the kids, don’t let that dissuade you from looking for the finer things. Luxury is the name of the game in Winchester, and house accommodation is no different. Sure, it should feel like a home away from home—but more like a really fancy home, where you don’t have to worry about cleaning or mowing the lawn. Yes, it’s as great as it sounds.
Make your next getaway truly your own. We’ve got plenty of holiday accommodation in Winchester with your name on it, so pack up your favourite books, wine and that playlist of summer hits from 2003. It’s your time to shine.
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