A street with cars, a Jeep, and a building with a sign that says "Visitor Center".

Charles Town Vacation Rentals

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Our top choices for Charles Town vacation rentals

1. Executive Suites

Executive Suites
3.0 star property
Winchester
The price is CA $360
CA $408 total
includes taxes & fees
Nov 14 - Nov 15
Executive Suites

2. Schilling House

Schilling House
3.0 star property
Bolivar
The price is CA $336
CA $431 total
includes taxes & fees
Nov 22 - Nov 23
Schilling House

3. Walk to Stores: Home in Historic Shepherdstown!

Walk to Stores: Home in Historic Shepherdstown!
3.0 star property
Shepherdstown
The price is CA $172
CA $506 total
includes taxes & fees
Nov 19 - Nov 20
Walk to Stores: Home in Historic Shepherdstown!

4. Cottage w/ Furnished Patio & Garden: Dtwn Leesburg

Cottage w/ Furnished Patio & Garden: Dtwn Leesburg
3.0 star property
Leesburg's Old and Historic District
The price is CA $581
CA $969 total
includes taxes & fees
Nov 22 - Nov 23
Cottage w/ Furnished Patio & Garden: Dtwn Leesburg
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Charles Town Hotel Reviews

Find out more about Charles Town

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . Seeing all the best attractions is bound to make you fall in love with Charles Town. Who knows, you may even be tempted to extend your vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Charles Town?

Yes, we have vacation rentals near top local attractions in Charles Town, or you can choose a more remote option if you're looking for relaxation. Charles Town is known for its casinos and entertainment choices. Make sure you have time to check out the cathedral while you're in the area.

What are some of the best vacation rentals that Charles Town has to offer?

Terra Alta - Incredible River Views and Hot Tub!: This Charles Town vacation home rental is located on a river and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a private yard, a selection of games, and a hot tub so you can immerse yourself in your vacation. Other favorite homes for rent in Charles Town are Charles Town Home w/ Private Pool & Hot Tub and The River House! Quiet Retreat on Shenandoah River.

How many vacation rentals will I find in Charles Town?

Choose from 15 Expedia vacation rentals in Charles Town for a memorable vacation.

What’s there to see and do in Charles Town?

Cultural attractions include Old Opera House, whereas Shenandoah River is a spot to enjoy nature. While here, Charles Town Library and Hollywood Casino at Charles Town Races are other places worth a visit.

What’s a vacation rental in Charles Town like?

A vacation rental is a private property where you can stay for a couple of days or more in Charles Town. Vacation rentals offer extras such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about cleanliness, a vacation rental can offer a sense of privacy away from shared hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for families.