Charles Town Holiday Rentals

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Holiday Rentals in Charles Town

Terra Alta - Incredible River Views and Hot Tub!
9.8 out of 10, Exceptional, (44)
"Stayed here for work. Had 5 guys at the house. Plenty of room and great deck to hang out on."
The price is NZ$809
per night
6 Jun - 7 Jun
Terra Alta - Incredible River Views and Hot Tub!
Modern Country House on the Shenandoah River
9.8 out of 10, Exceptional, (21)
"A group of 6 friends stayed at the house to do some bike riding wine & beer tasting in the area. We had a great time. The house worked out wonderfully."
Modern Country House on the Shenandoah River
Cozy Mountain Cabin w/ Steam Shower. Family Friendly!
10.0 out of 10, Exceptional, (28)
"This little cabin was great!! Comfortable beds. Very clean. Brigid the host was so responsive. Instructions were very clear. She even answered our questions about recommendations for a goos hiking trail! Highly recommend! I hope we will be back."
The price is NZ$535
per night
5 Jun - 6 Jun
Cozy Mountain Cabin w/ Steam Shower. Family Friendly!
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❤️ Secluded 1940s Romantic Tiny House on the River
10.0 out of 10, Exceptional, (41)
"The tiny house is exactly as described. Its small, clean, cozy and comfortable. The location right on the river is fantastic. Being able to have a fire right by the water each night was such a plus. In better weather would be a great put in for canoeing, kataking. Very close many historic sights, unique shops, and outdoor activities. The hosts are very thoughtful, kind and responsive. We will be staying again!!"
The price is NZ$235
per night
16 Jun - 17 Jun
❤️ Secluded 1940s Romantic Tiny House on the River
Cabin w Hot Tub, Indoor Pool / Gym Access, & Grill
9.6 out of 10, Exceptional, (8)
"Beautiful property, quiet, and very spacious. This property had everything we were looking for in a getaway. My family enjoyed our time together here. We did have a power outage and I let Tony know as soon as the power went out. He was quick to respond and even gave updates. Loved the communication from Tony throughout our whole experience. Definitely would stay here again and at another one of his properties."
The price is NZ$485
per night
3 Jun - 4 Jun
Cabin w Hot Tub, Indoor Pool / Gym Access, & Grill
Breathtaking views with an indoor private pool, come escape with us
9.8 out of 10, Exceptional, (227)
"Fantastic spot to spend a few days. Incredible house, fantastic amenities, and a beautiful location."
Breathtaking views with an indoor private pool, come escape with us
Charming "Cream of the Crop" Cape ~❤️of Middletown
10.0 out of 10, Exceptional, (101)
"This is our 2nd stay at the "Cape Cod". The house is quiet, clean, and modern. Heather is very responsive. The Middletown location provided us with convenient access for our outings to Gettysburg, Emmitsburg, MD and Frederick."
The price is NZ$414
per night
4 Jun - 5 Jun
Charming "Cream of the Crop" Cape ~❤️of Middletown
RIVERKEEPER INN, Waterfront Property on the Potomac River
9.4 out of 10, Exceptional, (104)
"We had a wonderful time, even in the rain! Easy river access and beautiful views of both the water and green spaces."
RIVERKEEPER INN, Waterfront Property on the Potomac River
Riverside cottage, minutes from historic Harpers Ferry; private river access!
9.8 out of 10, Exceptional, (56)
"Not much to say other than it was a great stay. Scott was super responsive for the few questions we had and everything was clean and comfortable."
The price is NZ$361
per night
2 Jun - 3 Jun
Riverside cottage, minutes from historic Harpers Ferry; private river access!
Charming Home with Yard Near Shenandoah River!
9.6 out of 10, Exceptional, (8)
"We had a good time at the place. The big kitchen table is perfect for gathering when the weather keeps you from the fabulous fire pit. We would go back if we had an occasion to."
Charming Home with Yard Near Shenandoah River!
Rustic Log Cabin with Private Dock on the Lake!
9.6 out of 10, Exceptional, (9)
"The location tucked away on the lake with a dock and kayaks and gravity lounge chairs, fireplace, large dock and gas grill were fabulous."
Rustic Log Cabin with Private Dock on the Lake!
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
10.0 out of 10, Exceptional, (93)
"We enjoyed our stay at this historic home in the middle of town. We loved sitting on the porch and we slept great both nights."
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
Antietam Creek - Quiet 2 Bedroom Cabin
9.4 out of 10, Exceptional, (71)
"Perfect quiet spot to relax and spend quality time! Cabin was as listed and was just what we needed!"
The price is NZ$540
per night
6 Jun - 7 Jun
Antietam Creek - Quiet 2 Bedroom Cabin
18th Century Stone Cottage minutes from historic Middleburg
10.0 out of 10, Exceptional, (16)
"We had a nice stay in a lovely rural location with nice outdoor terrace and quiet street for a long walk. Communication with the host was simple and straight forward."
The price is NZ$636
per night
10 Jun - 11 Jun
18th Century Stone Cottage minutes from historic Middleburg
The Oculus - Huge Cabin with a Hot Tub!
10.0 out of 10, Exceptional, (11)
"This property is so wonderful. Great location. Wonderfully comfortable beds! And very clean! We look forward to coming back!"
The Oculus - Huge Cabin with a Hot Tub!
White House Inn - Historic Home in Harpers Ferry!
10.0 out of 10, Exceptional, (15)
"The house was so much more beautiful and bigger in person than I realized from photos! The location is such an easy walk down into town. The host checked in with me several times to make sure I was doing okay and didn't need anything. Would book again!"
The price is NZ$1,208
per night
13 Jun - 14 Jun
White House Inn - Historic Home in Harpers Ferry!
Historic and Updated Farmhouse Built in 1808
10.0 out of 10, Exceptional, (114)
"We had a great stay! Thank you!"
Historic and Updated Farmhouse Built in 1808
New Wine Horse Country 10 Acre Lux Retreat amid historic sites. Stunning Views!
9.8 out of 10, Exceptional, (7)
"Great location, beautifully appointed - wish we’d had more time to enjoy the property."
The price is NZ$846
per night
31 May - 1 Jun
New Wine Horse Country 10 Acre Lux Retreat amid historic sites. Stunning Views!
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
9.6 out of 10, Exceptional, (81)
"My wife LOVED it here. Yes it’s an old cabin But it was furnished wonderfully and very comfortable. We had a great stay and have already recommended this place to a few friends. Over all I give it an A and this one ranks up in the top 5 of our vrbo vacation rentals"
The price is NZ$350
per night
6 Jun - 7 Jun
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Woodpecker Woods - Cozy Log Cabin w/ Hot Tub!
9.6 out of 10, Exceptional, (10)
"We enjoyed the cabin very much. We hiked during the day and was very relaxing coming back to the hot tub and a fire. Thank you for a great stay!!"
Woodpecker Woods - Cozy Log Cabin w/ Hot Tub!
Don't see what you're looking for?
See all available properties in Charles Town
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.

Other types of properties in Charles Town you may be interested in

The Inn at Charles Town
3.0 star property
8.4 out of 10, Very good, (337)
"N/A"
The price is NZ$189
per night
12 Jun - 13 Jun
The Inn at Charles Town
Rodeway Inn & Suites - Charles Town, WV
2.0 star property
8.8 out of 10, Excellent, (802)
"Great option for the price - really nice staff "
The price is NZ$132
per night
16 Jun - 17 Jun
Rodeway Inn & Suites - Charles Town, WV
Home2 Suites by Hilton Charles Town
3.0 star property
9.8 out of 10, Exceptional, (619)
"The hotel is nice and clean and offers very good breakfast. However the WiFi service is poor from our room. Hope they can improve that."
The price is NZ$293
per night
10 Jun - 11 Jun
Home2 Suites by Hilton Charles Town
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.

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

As much as you love your vacation rental, it’s always good to get out and explore to soak up Charles Town. 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 Charles Town. 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 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 holiday 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 Charles Town short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Charles Town?

Yes, there are holiday rentals close to the most popular sights in Charles Town, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Charles Town has to offer?

Terra Alta - Incredible River Views and Hot Tub!: This highly rated holiday home rental in Charles Town is located on a river, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub. Our travellers also rate Modern Country House on the Shenandoah River as a favourite home for rent in Charles Town.

How many holiday rentals will I find in Charles Town?

Choose from 10 Expedia holiday rentals in Charles Town for a memorable holiday.

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 holiday rental in Charles Town like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Charles Town. Holiday rentals provide amenities such as hot tubs, fire pits and patios so you'll be comfy for your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from shared hotel lifts and busy front desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for families.

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