Winchester Holiday Homes
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Featured Holiday Homes in Winchester

Secluded River Cabin Getaway (Masten Cabin)

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

Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub

Cozy place near Shenandoah National Park, Luray Caverns & 30min to Massanutten!

A private home in Bolivar with a hot tub and yard. Pet friendly!

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

Riverside cottage, minutes from historic Harpers Ferry! Private river access!

Cottage on King | Charming Historic Leesburg Home

Cozy Lakeside Homestead

Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

Newly renovated Farm cottage with Mountain views

Elevated Potomac River Retreat - King Suite - Riverfront - Large Screened Porch
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.
Winchester Holiday Homes essential information
Accommodation | 659 Holiday Homes |
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Lowest Price | |
Highest Price | |
Popular accommodation | Secluded River Cabin Getaway (Masten Cabin), Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!, Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub, Cozy place near Shenandoah National Park, Luray Caverns & 30min to Massanutten!, A private home in Bolivar with a hot tub and yard. Pet friendly!, Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly, Riverside cottage, minutes from historic Harpers Ferry! Private river access!, Cottage on King | Charming Historic Leesburg Home, Cozy Lakeside Homestead, Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex, Newly renovated Farm cottage with Mountain views , Elevated Potomac River Retreat - King Suite - Riverfront - Large Screened Porch |
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La Quinta Inn & Suites by Wyndham Winchester
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