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 "
Terra Alta - Incredible River Views and Hot Tub!

Charles Town Home w/ Private Pool & Hot Tub

10.0 out of 10, Exceptional, (40)
"Lots of space for everyone, excellent pool and hot tub"
Charles Town Home w/ Private Pool & Hot Tub

Modern Country House on the Shenandoah River

9.8 out of 10, Exceptional, (30)
"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

❤️ Secluded 1940s Romantic Tiny House on the River

10.0 out of 10, Exceptional, (49)
"Excellent little cabin right on the river and close to DT Sheperdstown which is a great town."
The price is AU$180
includes taxes & fees
20 Jan - 21 Jan
❤️ Secluded 1940s Romantic Tiny House on the River

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

9.6 out of 10, Exceptional, (89)
"Great year round location. Owners are nearby if issues occur. HIGHLY RECOMMENDED. "
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, (244)
"We thoroughly enjoyed the cozy lodge vibe and the different spaces it offered our group. The host, Leslie, was always available for any questions we had. She also had the place decorated for Christmas which warmed our hearts!! Thank you Bear Chase for a great weekend. "
Breathtaking views with an indoor private pool, come escape with us

Woodpecker Woods - Cozy Log Cabin w/ Hot Tub!

9.8 out of 10, Exceptional, (20)
"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!

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!

Bear Chase Cottage

10.0 out of 10, Exceptional, (32)
"The cabin was perfect! Clean and cozy. We wish we could have extended our stay! We will definitely come back! "
Bear Chase Cottage

1800s Family Farmhouse with Huge Yard- PRIVATE TRAIL WALK TO WINE!

10.0 out of 10, Exceptional, (46)
"With grandparents and 2 families with children, not only was the house perfect but the fenced yard was huge and spectacular. We didn’t use the hot tub, but there was plenty of good space for adults, too. We gathered for a family wedding, but the space enabled us to spend a few wonderful relaxing days with family we rarely see. Communication with Leora was prompt and accommodating. 5 stars all around! Thank you!"
1800s Family Farmhouse with Huge Yard- PRIVATE TRAIL WALK TO WINE!

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

9.8 out of 10, Exceptional, (51)
"The place was adorable. The view was amazing!"
The price is AU$860
includes taxes & fees
9 Jan - 10 Jan
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!

Gruner Bungalow at Otium Cellars

9.8 out of 10, Exceptional, (92)
"Wonderful Thanksgiving in a wonderful home with our family."
Gruner Bungalow at Otium Cellars

Rustic Log Cabin with Private Dock on the Lake!

9.6 out of 10, Exceptional, (12)
"Amazing location!!! 18 minutes from a cluster of wineries; quiet and relaxing. Definitely will be visiting again "
The price is AU$661
includes taxes & fees
5 Jan - 6 Jan
Rustic Log Cabin with Private Dock on the Lake!

RIVERKEEPER INN, Waterfront Property on the Potomac River

9.2 out of 10, Wonderful, (116)
"Went to Harper’s Ferry for our 25th wedding anniversary and wanted to stay near the water since we usually stay in town. Found this property and it was perfect. Sits on property with owners who we met and their dog Chloe who was an absolute sweetheart. If you are looking for a piece of serenity you will find it at the Riverkeeper Inn. Very nice and quiet neighborhood. The property was tidy and clean and you get to use the gazebo or decks near the water to chill and if it wasn’t too chilly would...
RIVERKEEPER INN, Waterfront Property on the Potomac River

Cozy Mountain Cabin w/ Steam Shower. Family Friendly!

10.0 out of 10, Exceptional, (52)
"It was so nice. We were bummed to only be there one night. Such a lovely set up. Would definitely recommend to anyone. Although I have to say the trip up the hill was similar to a roller coaster ride, such fun."
The price is AU$486
includes taxes & fees
14 Jan - 15 Jan
Cozy Mountain Cabin w/ Steam Shower. Family Friendly!

Walk to Potomac River and downtown Harpers Ferry

10.0 out of 10, Exceptional, (110)
"The house was amazing, great views and a great layout that allowed for us to hang as a group or have some privacy. Very convenient to everything we wanted to do; Harper’s Ferry, Ziplining (or rafting based on time of year), and the Brewery that we went to on the last night felt like it was almost walking distance. Definitely recommend and would stay again in a heartbeat. "
Walk to Potomac River and downtown Harpers Ferry

Charming "Cream of the Crop" Cape ~❤️of Middletown

10.0 out of 10, Exceptional, (117)
"We were looking for a quiet getaway location from the Black Friday and Small Business Saturday crowds, but also a location that was close to several small towns near the area...and this property checked all boxes! Everywhere you go within 20-30 minutes is a delight for the history, art, music collector, foodie, entertainment, wine, distillery, brewery, or shopping fanatic...a delightful home and one we hope to visit again!"
The price is AU$403
includes taxes & fees
5 Jan - 6 Jan
Charming "Cream of the Crop" Cape ~❤️of Middletown

Secluded Cabin a Stone's Throw From the A.T.!

9.8 out of 10, Exceptional, (17)
"We were charmed by the house and pleased with all the amenities. We would definitely stay there again. "
Secluded Cabin a Stone's Throw From the A.T.!

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

9.6 out of 10, Exceptional, (50)
"My husband and I along with our 2 small dogs had a wonderful stay at this lovely mountain retreat. The cabin was clean and comfortable and had everything that we needed to cook breakfast and an easy dinner each evening. The property was beautiful with lots of tall old growth trees that were beautiful with the fall colors and even though it was in a community you felt like you were in a secluded mountain retreat because most of the homes were obsured by the trees; and it is on a dead end road...
The price is AU$504
includes taxes & fees
14 Jan - 15 Jan
Hot Tub, Deck/Grill, Game Room, WiFi at Cute Cabin

18th Century Stone Cottage minutes from historic Middleburg

10.0 out of 10, Exceptional, (34)
"Nice place! Clean, beautiful, and located just two miles from town. "
The price is AU$642
includes taxes & fees
6 Jan - 7 Jan
18th Century Stone Cottage minutes from historic Middleburg
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
8.6 out of 10, Excellent, (432)
"The Inn at charlestown was amazing from the staff, the room especially the bed. Me and my mom had a very relaxing time while celebrating my birthday on Dec 25th. The only issue i had was walkiing through secondhand smoke in order to reach the non-smoking section in the back of the casino (that still carried the smell), other than that i had a good time at the casino."
The price is AU$215
includes taxes & fees
16 Jan - 17 Jan
The Inn at Charles Town

Rodeway Inn & Suites - Charles Town, WV

2.0 star property
8.8 out of 10, Excellent, (905)
"Quiet atmosphere quick check in and right outside if the casino. Good Mediterranean restaurant downstairs. "
The price is AU$115
includes taxes & fees
5 Jan - 6 Jan
Rodeway Inn & Suites - Charles Town, WV

Home2 Suites by Hilton Charles Town

3.0 star property
9.6 out of 10, Exceptional, (704)
"The front desk attendant was fantastic, and the room was clean and comfortable. The breakfast was a big disappointment."
The price is AU$275
includes taxes & fees
23 Jan - 24 Jan
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.

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 12 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.