Vacation Homes in Winchester
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Featured Vacation Homes in Winchester

Walk to Harpers Ferry! Dog-friendly. Beautiful Views.

Historical home, walkable to many restaurants and shops.

Luxury NEW! Woodhaven Reserve! Private Pool + Hot Tub

Secluded River Cabin Getaway (Masten Cabin)

Harpers Ferry Luxury, Spa Bathroom, Movie Room, high-end design and furnishings

Charming 3-Bedroom Home in historic Harpers Ferry: Pet Friendly!

On the river ~ hot tub ~ serene river views ~ fire pit

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

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

Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.

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

Mountain View Bungalow in Front Royal
Top trending hotels in Winchester

The George Washington Hotel, A Wyndham Grand Hotel
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 | 643 Vacation Homes |
|---|---|
Lowest Price | CA $104 |
Highest Price | CA $628 |
Popular accommodation | Walk to Harpers Ferry! Dog-friendly. Beautiful Views., Historical home, walkable to many restaurants and shops. , Luxury NEW! Woodhaven Reserve! Private Pool + Hot Tub, Secluded River Cabin Getaway (Masten Cabin), Harpers Ferry Luxury, Spa Bathroom, Movie Room, high-end design and furnishings, Charming 3-Bedroom Home in historic Harpers Ferry: Pet Friendly!, On the river ~ hot tub ~ serene river views ~ fire pit, Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly, Riverside cottage, minutes from historic Harpers Ferry! Private river access!, Family-friendly, thoughtfully modernized, historic home in Harpers Ferry., A private home in historic Bolivar with a hot tub and yard. Pet friendly!, Mountain View Bungalow in Front Royal |





