Charles Town Vacation Rentals

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Sep 25 - Sep 26
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Sep 26 - Sep 27
This weekend
Sep 26 - Sep 28
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Oct 3 - Oct 5

Vacation Rentals in Charles Town

Stunning Views, Riverfront Privacy, 18-Acre Estate - Near Hikes, Wine/Breweries!
Terrace/patio

Stunning Views, Riverfront Privacy, 18-Acre Estate - Near Hikes, Wine/Breweries!

9.8 out of 10, Exceptional, (23)
"Most enjoyable two night stay. Wish we had the time to spend more time in this lovely house and properity."
Stunning Views, Riverfront Privacy, 18-Acre Estate - Near Hikes, Wine/Breweries!
Terra Alta - Incredible River Views and Hot Tub!
Outdoor spa tub

Terra Alta - Incredible River Views and Hot Tub!

9.6 out of 10, Exceptional, (60)
"We had a great time! The house overlooks the river and we loved the hot tub and fire pit! "
The price is ￥14,761
￥59,319 total
includes taxes & fees
Oct 2 - Oct 3
Terra Alta - Incredible River Views and Hot Tub!
Modern Country House on the Shenandoah River
Property grounds

Modern Country House on the Shenandoah River

9.8 out of 10, Exceptional, (41)
"The views are beautiful and the house was the perfect size for a group of 7 friends. We had a great time!"
Modern Country House on the Shenandoah River
The River House
Fridge, microwave, oven, stovetop

The River House

10.0 out of 10, Exceptional, (7)
"Host communicated well. Great location right on the river. Family had a great time. "
The price is ￥17,403
￥43,196 total
includes taxes & fees
Sep 29 - Sep 30
The River House
Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry
Microwave

Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry

9.4 out of 10, Exceptional, (14)
"Small basement apartment had all we needed and wanted. Wonderful location. "
The price is ￥14,613
￥25,312 total
includes taxes & fees
Sep 29 - Sep 30
Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry
Breathtaking View with an Indoor Pool
Outdoor dining

Breathtaking View with an Indoor Pool

9.8 out of 10, Exceptional, (258)
"Great Property"
Breathtaking View with an Indoor Pool
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.
Outdoor dining

Whiskey Hill Cabin a Mountain escape in Virginia Wine country.

10.0 out of 10, Exceptional, (93)
"Very nice relaxing getaway, quite how do you spell quiet and serene location. "
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.
The Oculus - Huge Cabin with a Hot Tub!
Terrace/patio

The Oculus - Huge Cabin with a Hot Tub!

9.6 out of 10, Exceptional, (24)
"This was a great place for our vacation."
The price is ￥14,761
￥64,243 total
includes taxes & fees
Oct 2 - Oct 3
The Oculus - Huge Cabin with a Hot Tub!
❤️ Secluded 1940s Romantic Tiny House on the River
Property grounds

❤️ Secluded 1940s Romantic Tiny House on the River

10.0 out of 10, Exceptional, (61)
"We truly loved this location and definitely will be back!"
The price is ￥5,978
￥15,611 total
includes taxes & fees
Oct 5 - Oct 6
❤️ Secluded 1940s Romantic Tiny House on the River
RIVERKEEPER INN, Waterfront Property on the Potomac River
Terrace/patio

RIVERKEEPER INN, Waterfront Property on the Potomac River

9.4 out of 10, Exceptional, (128)
"Beautiful location right on the Potomac River."
RIVERKEEPER INN, Waterfront Property on the Potomac River
18th Century Stone Cottage minutes from historic Middleburg
Exterior

18th Century Stone Cottage minutes from historic Middleburg

10.0 out of 10, Exceptional, (47)
"What a peaceful place and wonderful views."
The price is ￥40,926
￥59,085 total
includes taxes & fees
Oct 26 - Oct 27
18th Century Stone Cottage minutes from historic Middleburg
Blue Ridge Getaway - Sunset Views, A.T. Access
Exterior

Blue Ridge Getaway - Sunset Views, A.T. Access

10.0 out of 10, Exceptional, (59)
"My girlfriend and I had a wonderful weekend escaping the hustle and bustle of the city. The view was spectacular and the property was perfect!"
The price is ￥14,761
￥53,889 total
includes taxes & fees
Oct 1 - Oct 2
Blue Ridge Getaway - Sunset Views, A.T. Access
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
Exterior detail

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

10.0 out of 10, Exceptional, (132)
"The house was perfect, right in the middle of historic Harper’s Ferry. We all had the best time! "
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
Antietam Creek - Quiet 2 Bedroom Cabin
Interior

Antietam Creek - Quiet 2 Bedroom Cabin

9.4 out of 10, Exceptional, (85)
"Cool even with no AC. Key is to open windows at night let the coolness in, Close windows and coverings during daytime. Fans on continuously to circulate the air… Chefs kiss!!"
The price is ￥29,522
￥48,661 total
includes taxes & fees
Sep 29 - Sep 30
Antietam Creek - Quiet 2 Bedroom Cabin
Secluded Cabin a Stone's Throw From the A.T.!
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (33)
"We enjoyed the beautiful views and the house had everything we wanted."
The price is ￥14,761
￥57,509 total
includes taxes & fees
Oct 2 - Oct 3
Secluded Cabin a Stone's Throw From the A.T.!
Historic cozy farmhouse in the ❤️ of Myersville , MD close to Rt 70! Welcome Home
Fridge, microwave, oven, stovetop

Historic cozy farmhouse in the ❤️ of Myersville , MD close to Rt 70! Welcome Home

9.4 out of 10, Exceptional, (104)
"Great little farm house in a quaint little town "
The price is ￥23,662
￥43,223 total
includes taxes & fees
Oct 9 - Oct 10
Historic cozy farmhouse in the ❤️ of Myersville , MD close to Rt 70! Welcome Home
Enchanting Cottage, walk to Downtown Harpers Ferry
Terrace/patio

Enchanting Cottage, walk to Downtown Harpers Ferry

9.6 out of 10, Exceptional, (41)
"This place was perfect for our one-night stay in Harpers Ferry. Its location is in easy walking distance of the main sites. The house is old but charming. "
The price is ￥30,434
￥50,104 total
includes taxes & fees
Sep 30 - Oct 1
Enchanting Cottage, walk to Downtown Harpers Ferry
Walk to Harpers Ferry! Dog-friendly. Beautiful Views.
Interior

Walk to Harpers Ferry! Dog-friendly. Beautiful Views.

10.0 out of 10, Exceptional, (69)
"The property was clean, quiet and the neighborhood was safe. We had a great time and tawny was a great host."
Walk to Harpers Ferry! Dog-friendly. Beautiful Views.
Cozy Cabin w/ Hot Tub, Arcade & Fire Pit perfect for up to 8 people
Outdoor dining

Cozy Cabin w/ Hot Tub, Arcade & Fire Pit perfect for up to 8 people

8.4 out of 10, Very Good, (24)
"This house"
Cozy Cabin w/ Hot Tub, Arcade & Fire Pit perfect for up to 8 people
Historical cottage in the town of Paris
Exterior

Historical cottage in the town of Paris

9.8 out of 10, Exceptional, (48)
"we enjoy our stay everytime"
Historical cottage in the town of Paris
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

Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

10/10 Excellent
"Everything was great except I feel the website should have updated that the restaurant was closed. The beds were amazing and had some issues connecting to the WiFi, but overall a good stay. "
Maria 1-night trip
Posted 18 hours ago
Holiday Inn Winchester Se-Historic Gateway by IHG

Find out more about Charles Town

Find out more about Charles Town

Search for holiday rentals in Charles Town on Expedia! You can easily find your home rentals, villas, holiday apartments in Charles Town using one of the methods below:

  • View our selection of featured holiday rentals in Charles Town
  • Use the map to find apartments and other holiday homes in the Charles Town neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Charles Town while they last

Look no further and take a look at our great range of rental properties in Charles Town!

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?

Stunning Views, Riverfront Privacy, 18-Acre Estate - Near Hikes, Wine/Breweries!: Visitors give good reviews to this Charles Town vacation home rental, which is located on a river and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals will I find in Charles Town?

Choose from 12 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, Jefferson County Courthouse and Charles Town Library 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.