Charles Town Holiday Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Charles Town

Property grounds
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."
Terra Alta - Incredible River Views and Hot Tub!
Property grounds
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
Smart TV, DVD player, books, video library
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$541
per night
30 May - 31 May
Cozy Mountain Cabin w/ Steam Shower. Family Friendly!
Save an average of 15% on thousands of hotels when you're signed in
View from property
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
TV, fireplace, books, stereo
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$491
per night
29 May - 30 May
Cabin w Hot Tub, Indoor Pool / Gym Access, & Grill
Fridge, microwave, oven, stovetop
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
Property grounds
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$363
per night
6 Jun - 7 Jun
Riverside cottage, minutes from historic Harpers Ferry; private river access!
Beach
❤️ 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$237
per night
9 Jun - 10 Jun
❤️ Secluded 1940s Romantic Tiny House on the River
Property grounds
Charming "Cream of the Crop" Cape ~❤️of Middletown
10.0 out of 10, Exceptional, (100)
"Perfect location in historic Middletown. Our daughter stayed over night to be our driver to graduations. She recommends a circulating fan for the basement bedroom! Apparently, we, at the age of 83, kept the house a little too warm!"
The price is NZ$408
per night
30 May - 31 May
Charming "Cream of the Crop" Cape ~❤️of Middletown
Exterior
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
10.0 out of 10, Exceptional, (92)
"We had a lovely stay in this beautiful Harpers Ferry home. It was so amazing to stay in the historical area and be close and able to walk to all the National Park sites. We were most attracted to that lovely porch and enjoyed our coffee there in the early morning, watching the town come to life. We also liked afternoons reading and napping there and an evening glass of wine after dinner. The kitchen was well stocked with everything we needed, the furniture and beds were very comfortable. We will...
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
Exterior
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$640
per night
9 Jun - 10 Jun
18th Century Stone Cottage minutes from historic Middleburg
Exterior
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$852
per night
1 Jun - 2 Jun
New Wine Horse Country 10 Acre Lux Retreat amid historic sites. Stunning Views!
Fridge, microwave, stovetop, dishwasher
Charming Home with Yard Near Shenandoah River!
9.6 out of 10, Exceptional, (7)
"The hosts received a notice that we had lost heat at the house. We actually did not, but they were out the next morning to check the furnace and brought two space heaters we did not have to use. Really enjoyed our stay."
Charming Home with Yard Near Shenandoah River!
Property grounds
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!
View from property
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$547
per night
10 Jun - 11 Jun
Antietam Creek - Quiet 2 Bedroom Cabin
Property grounds
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!
Exterior
Cozy Cottage
9.2 out of 10, Wonderful, (18)
"Cottage is quaint, with modern design. Perfect for my husband and I and our pup. Very clean, with tasteful decor. Within walking distance to town. Had everything you need."
The price is NZ$351
per night
27 May - 28 May
Cozy Cottage
Exterior
Dome Of Your Dreams!
8.4 out of 10, Very good, (42)
"We chose the Dome for our week long stay due to it's proximity to the state parks in northern Virginia, AND we'd choose to stay her again. We visited several new establishments, breweries, distilleries, and restaurants that have popped up or have missed since moving to central Virginia. We were out of the house everyday and then most nights came back and turned in for the evening. We couldn't zone out in front of the TV on the main living area because there isn't one. There is one downstairs...
Dome Of Your Dreams!
Property grounds
Family Gathering Space with a PRIVATE TRAIL WALK TO WINE!
10.0 out of 10, Exceptional, (36)
"We visited for a friends weekend and loved our stay. The bedrooms and communal areas were comfortable and great for a party of 7. The hot tub and outdoor fireplace were a hit. The property was peaceful. We didn’t walk to winery bc it was raining but we did drive (a minute) there and that was a lovely winery trip. The host was proactive asking if we needed anything before and during our stay. She was helpful w recommendation for restaurants and kind to offer any help while we were there (which...
Family Gathering Space with a PRIVATE TRAIL WALK TO WINE!
Fridge, microwave, oven, stovetop
Cozy home near Casino, Breweries, Historical attractions, National Park & more
10.0 out of 10, Exceptional, (12)
"The home is beautiful! The owners did an amazing job to make us feel welcomed and at home. They provided us we unexpected amenities like coffee creamer, bottle water and even a bottle of wine. We greatly appreciated the free Netflix especially since ti rained during part of our stay. The location is ideal for our weekend adventures."
Cozy home near Casino, Breweries, Historical attractions, National Park & more
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

Exterior
The Inn at Charles Town
3.0 star property
8.4 out of 10, Very good, (334)
"The Inn was everything we needed. Front Desk Team was very polite and helpful. Shuttle driver was friendly and the shuttle was timely. The breakfast was "continental" but offered many options. I would definitely stay again."
The price is NZ$187
per night
10 Jun - 11 Jun
The Inn at Charles Town
Hiking
Rodeway Inn & Suites - Charles Town, WV
2.0 star property
8.8 out of 10, Excellent, (798)
"Great."
The price is NZ$133
per night
27 May - 28 May
Rodeway Inn & Suites - Charles Town, WV
Terrace/patio
Home2 Suites by Hilton Charles Town
3.0 star property
9.8 out of 10, Exceptional, (617)
"Very pet friendly - clean - great staff. Definitely stay again. Also really cool racetrack casino 3 minutes away. "
The price is NZ$279
per night
9 Jun - 10 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.

Recent reviews of Charles Town properties
Expedia verified reviews