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, (52)
"Está bien hermosa la casa "
The price is AU$799
includes taxes & fees
1 Dec - 2 Dec
Terra Alta - Incredible River Views and Hot Tub!

Modern Country House on the Shenandoah River

9.8 out of 10, Exceptional, (29)
"Overall was beautiful. Very easy to communicate with the owner. The view was breathtaking. I’d definitely recommend this to my other families and friends. Thanks again for making our stay so pleasant. "
Modern Country House on the Shenandoah River

Charles Town Home w/ Private Pool & Hot Tub

10.0 out of 10, Exceptional, (39)
"Lots of space for everyone, excellent pool and hot tub"
Charles Town Home w/ Private Pool & Hot Tub

❤️ Secluded 1940s Romantic Tiny House on the River

10.0 out of 10, Exceptional, (47)
"My husband and I stayed here to celebrate our second anniversary. We wanted just a quiet getaway and it was the perfect place. Definitely will have to come back again."
The price is AU$172
includes taxes & fees
9 Dec - 10 Dec
❤️ Secluded 1940s Romantic Tiny House on the River

Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!

10.0 out of 10, Exceptional, (110)
"This property could not have been more quaint and peaceful. My husband, two dogs and I enjoyed the long weekend, walking the trails and taking in the history of Harper’s Ferry. I would highly recommend this property to anyone looking for a quiet getaway. The location could not be better for seeing the town on foot. The property was clean and so neatly appointed. Breathtaking views! "
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!

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

9.8 out of 10, Exceptional, (86)
"We were looking to unplug for a night, and this cottage was the perfect spot! Clean and well kept, calm and quiet surroundings. One note is that the WiFi was not working. We didn’t need it for our trip, but something to keep in mind!"
The price is AU$341
includes taxes & fees
25 Nov - 26 Nov
Riverside cottage, minutes from historic Harpers Ferry! Private river access!

Breathtaking views with an indoor private pool, come escape with us

9.8 out of 10, Exceptional, (240)
"Great place to relax & enjoy! We loved the pool & hot tub as well abundant indoor/outdoor space. There was a musty smell that lingered on all my clothes and I stayed in the very top floor master & put my clothes in dresser and closet. You may need a dehumidifier in that closet…."
Breathtaking views with an indoor private pool, come escape with us

Cozy Mountain Cabin w/ Steam Shower. Family Friendly!

10.0 out of 10, Exceptional, (51)
"Comfy cabin with everything topline. Loved the sunroom and the steam shower. Daily watching deer feed and stroll through the yard below. Gus wasn’t happy about it but he still watched through floor to ceiling windows."
The price is AU$467
includes taxes & fees
2 Dec - 3 Dec
Cozy Mountain Cabin w/ Steam Shower. Family Friendly!

The Oculus - Huge Cabin with a Hot Tub!

9.8 out of 10, Exceptional, (15)
"Rustic."
The Oculus - Huge Cabin with a Hot Tub!

Antietam Creek - Quiet 2 Bedroom Cabin

9.4 out of 10, Exceptional, (76)
"We were visiting with family in Boonsboro and arrived late in the evening and left by 9am, but everything was there that we would have needed for a longer stay, which we have planned for Thanksgiving. Kitchen was very well equipped, the space was inviting, the beds were comfy and the view out the back was great, Looking forward to our return!"
The price is AU$520
includes taxes & fees
25 Nov - 26 Nov
Antietam Creek - Quiet 2 Bedroom Cabin

Best location! The Pullman Apt @ historic 1799 Inn

9.4 out of 10, Exceptional, (25)
"When I booked this stay, I didn’t realize how much history we would be surrounded by! Museums, shops and great restaurants within walking distance. Plenty of hiking all around with access to the Appalachian trail. Access to e-bikes. Breweries and groceries just a short drive away"
The price is AU$294
includes taxes & fees
12 Dec - 13 Dec
Best location! The Pullman Apt @ historic 1799 Inn

Hot Tub, Deck/Grill, Game Room, WiFi at Cute Cabin

9.8 out of 10, Exceptional, (46)
"The location is not convenient for access, and the master bedroom cannot take a shower"
The price is AU$589
includes taxes & fees
12 Dec - 13 Dec
Hot Tub, Deck/Grill, Game Room, WiFi at Cute Cabin

Whiskey Hill Cabin in Virginia Wine country. Close to Fox Meadow & Capstone!

10.0 out of 10, Exceptional, (76)
"Whisky Hill is an amazing cabin. My husband and I enjoyed our stay. Everything was clean, and had everything we needed. It was not difficult at all to find. We thoroughly enjoyed our time and can’t wait to be back. It was a great find!! Highly recommend if coming to the Linden area. "
Whiskey Hill Cabin in Virginia Wine country. Close to Fox Meadow & Capstone!

Woodpecker Woods - Cozy Log Cabin w/ Hot Tub!

9.8 out of 10, Exceptional, (19)
"My friends and I always choose a new cabin for our annual fall getaway. We've not had a bad experience yet. Mountain Mama's Woodpecker Woods did not disappoint, either! Comfortable, warm, clean, spacious log cabin. It had everything we needed. In fact, it was so relaxing, we never made it to the hot tub. We did visit Harper's Ferry Park and enjoyed walking the hiking trail to the downtown area. :-) We especially loved the close proximity to the Washington, DC Metro area. If there was anything...
Woodpecker Woods - Cozy Log Cabin w/ Hot Tub!

Rustic Log Cabin with Private Dock on the Lake!

9.8 out of 10, Exceptional, (11)
"Amazing location!!! 18 minutes from a cluster of wineries; quiet and relaxing. Definitely will be visiting again "
Rustic Log Cabin with Private Dock on the Lake!

18th Century Stone Cottage minutes from historic Middleburg

10.0 out of 10, Exceptional, (32)
"Nice place! Clean, beautiful, and located just two miles from town. "
The price is AU$621
includes taxes & fees
5 Dec - 6 Dec
18th Century Stone Cottage minutes from historic Middleburg

RIVERKEEPER INN, Waterfront Property on the Potomac River

9.4 out of 10, Exceptional, (113)
"Enjoyed sitting on the deck above the river in the evenings, quiet and peaceful looking forward to staying there again."
RIVERKEEPER INN, Waterfront Property on the Potomac River

Sunny Streams Cabin - Sunset Views w/ a Hot Tub!

9.8 out of 10, Exceptional, (50)
"The place was adorable. The view was amazing!"
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!

Waterfront property in Harpers Ferry - Private River Access

10.0 out of 10, Exceptional, (21)
"Our stay at this vacation home was very enjoyable! The house was clean, well maintained and comfortable. It is located on a nice piece of property with a beautiful view of the Shenandoah River. The owner provided a lot of necessities like bed sheets, bath towels, soap, shampoo and even coffee supplies. The house is up to date and has a nice basement entertainment area. The fire pit area near the river was probably our favorite amenity. We enjoyed it on a couple evenings while enjoying the...
Waterfront property in Harpers Ferry - Private River Access

Gruner Bungalow at Otium Cellars

9.8 out of 10, Exceptional, (87)
"This was our third time staying at this beautiful property for our strategic planning session, and once again, it was a fantastic experience. The house is always spotless, spacious, and beautifully decorated, making it feel like a true home away from home. The host provided delicious meals throughout our stay, which added an extra level of convenience and enjoyment. Each meal was thoughtfully prepared and absolutely delicious—perfect for keeping our team energized and focused. The peaceful...
Gruner Bungalow at Otium Cellars
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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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, (420)
"The staff made this experience fantastic! They were so nice!"
The price is AU$181
includes taxes & fees
25 Nov - 26 Nov
The Inn at Charles Town

Rodeway Inn & Suites - Charles Town, WV

2.0 star property
8.8 out of 10, Excellent, (883)
"What I liked was the overall rating was higher than some of the brand named motels. Plus Rodeway was a lot cheaper than the other big dogs. Clean, quiet, friendly and excellent location to casino. "
The price is AU$118
includes taxes & fees
8 Dec - 9 Dec
Rodeway Inn & Suites - Charles Town, WV

Days Inn by Wyndham Charles Town/Harpers Ferry

2.0 star property
8.2 out of 10, Very good, (996)
"Just right"
The price is AU$116
includes taxes & fees
26 Nov - 27 Nov
Days Inn by Wyndham Charles Town/Harpers Ferry
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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. It offers a private garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday. 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 11 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, Jefferson County Courthouse 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.