Vacation Homes in Winchester
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Featured Vacation Homes in Winchester

Secluded River Cabin Getaway (Masten Cabin)

The Blue Pearl by Zen Living

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

Cottage on King | Charming Historic Leesburg Home

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

Cozy Lakeside Homestead

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

Newly renovated Farm cottage with Mountain views
Top trending hotels in Winchester

Comfort Inn & Suites
Vacation Rentals in Winchester
What kind of vacation do you want in Winchester? The answer to that question will help you choose the right lodging for your stay. The wise wanderer knows that a vacation rental is an essential part of the traveling experience. It’s more than just a place to crash at night—it’s where you wake up in the morning, where you lounge when you’re not exploring, and it’s the starting point for all your adventures. No matter what type of vacation homes strike your fancy, Travelocity has something in Winchester that will speak to you.
Do you want a fully equipped kitchen so you can exercise your culinary mastery and impress your travel buddies? How about a romantic terrace for your anniversary trip? Have you always wished to fall asleep to the sound of waves crashing on the shore? One of our vacation home rentals is bound to add that extra magic to your trip. In fact, we’ve got plenty of options lined up just for you in Winchester, including luxury vacation rentals. On a budget? We can work with your funds and still give you a great place to sleep at night.
Take a look at what we have on offer. You’ll find rentals close to the big tourist draws, as well as rentals that keep you away from the crowd. Consider vacation rentals a little off the beaten path where you can live like a local and discover hidden gems that never make it to the tourist sites. Book through Travelocity and start your getaway today.
Winchester Vacation Homes essential information
Accommodation | 659 Vacation Homes |
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Lowest Price | CA $94 |
Highest Price | CA $217 |
Popular accommodation | Secluded River Cabin Getaway (Masten Cabin), The Blue Pearl by Zen Living, 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, Cottage on King | Charming Historic Leesburg Home, Riverside cottage, minutes from historic Harpers Ferry! Private river access!, Cozy Lakeside Homestead, Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex, Newly renovated Farm cottage with Mountain views |