Charles Town Holiday Rentals

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Holiday Rentals in Charles Town

The River House

10.0 out of 10, Exceptional, (4)
"Host communicated well. Great location right on the river. Family had a great time. "
The price is NZ$599
includes taxes & fees
9 July - 10 July
The River House

Terra Alta - Incredible River Views and Hot Tub!

9.8 out of 10, Exceptional, (57)
"Multiple generations enjoyed this lovely house with plenty of space, well stocked kitchen, and great location for winery visits. Highlights include extra sleeping space, local coffee provided by the host, and the hottub! Gorgeous views and responsive hosy! "
The price is NZ$663
includes taxes & fees
9 July - 10 July
Terra Alta - Incredible River Views and Hot Tub!

Charming 2-Bedroom Basement Apartment with AC, WiFi in enchanting Leesburg

9.0 out of 10, Wonderful, (2)
"The apartment is great. I suspect it would be particularly awesome for a long-term stay. It's a basement apartment, so stairs weren't a surprise. Obviously, if you're not mobile, you won't pick this apartment. However, if you're a little wobbly, the stairs only have one handrail (it's not sketchy, but I rely pretty heavily on my handrails, and this one was not comforting), the bathroom floor is shiny and terrifying, the walk to the unit is bumpy, with lots of tree roots, uphill, and possibly...
The price is NZ$560
includes taxes & fees
8 July - 9 July
Charming 2-Bedroom Basement Apartment with AC, WiFi in enchanting Leesburg

The Cottage on Royal - Historic Leesburg Home

10.0 out of 10, Exceptional, (11)
"Cute little house perfect for a small town getaway. The house was a perfect fit for my family of 5. We were able to walk to the shops and enjoyed a nice day of shopping. We will be back!"
The price is NZ$756
includes taxes & fees
14 July - 15 July
The Cottage on Royal - Historic Leesburg Home

'Thomson Farm' Classic Home < 10 Mi to Vineyards!

10.0 out of 10, Exceptional, (30)
"Charming country home with spacious kitchen and plenty of room to gather. Each bedroom has own updated bathroom- perfect for large groups. Plenty of parking, too."
The price is NZ$3,047
includes taxes & fees
8 July - 9 July
'Thomson Farm' Classic Home < 10 Mi to Vineyards!

Quaint Royal Cottage @ Historic Leesburg

2.0 star property
10.0 out of 10, Exceptional, (8)
"Location was great! We enjoyed our stay in this old historical home that has been completely updated. Property manager was super communicative and easy to work with. 10 out of 10 would stay here again. "
The price is NZ$790
includes taxes & fees
21 July - 22 July
Quaint Royal Cottage @ Historic Leesburg

Retreat in Historic Downtown Leesburg - Walkable to Everything!

10.0 out of 10, Exceptional, (3)
"The house was immaculate, easy to use and walking distance to everything in downtown Leesburg. We would stay again!"
Retreat in Historic Downtown Leesburg - Walkable to Everything!

Cottage on King | Charming Historic Leesburg Home

9.6 out of 10, Exceptional, (52)
"Walkable to downtown historic Leesburg. Clean and super cute little house. Would stay again! "
The price is NZ$517
includes taxes & fees
9 July - 10 July
Cottage on King | Charming Historic Leesburg Home

Cozy home centrally located to historical old-town leesburg w/ HotTub & Firepit!

10.0 out of 10, Exceptional, (14)
"The house is well maintained and furnished, and the outdoor space is lovely. We had a great weekend in Leesburg and would come again. "
The price is NZ$701
includes taxes & fees
14 July - 15 July
Cozy home centrally located to historical old-town leesburg w/ HotTub & Firepit!

Historic Hideaway

10.0 out of 10, Exceptional, (18)
"I love this place. It was clean and the host was very attentive. I wish it was warmer because the downtown area has lot of cool places. I highly recommend this spot! "
The price is NZ$503
includes taxes & fees
9 July - 10 July
Historic Hideaway

Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

9.8 out of 10, Exceptional, (49)
"Visiting family over the holidays. Our trip was great. Location was perfect. Rental house accommodations fulfilled our needs, was clean and had everything we needed. Will definitely stay again. "
The price is NZ$406
includes taxes & fees
8 July - 9 July
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

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

10.0 out of 10, Exceptional, (123)
"Visited nice restaurants, brew pubs, antique shops. House was perfect for us. Very clean and well equipped. "
The price is NZ$514
includes taxes & fees
25 July - 26 July
Charming "Cream of the Crop" Cape ~❤️of Middletown

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

9.4 out of 10, Exceptional, (100)
"It is a lovely home and we had a lovely time"
The price is NZ$483
includes taxes & fees
10 July - 11 July
Historic cozy farmhouse in the ❤️ of Myersville , MD close to Rt 70! Welcome Home

Timeless Elegance in Restored Suite – King Bed & Private Spa Bath

The price is NZ$1,060
includes taxes & fees
13 July - 14 July
Timeless Elegance in Restored Suite – King Bed & Private Spa Bath

Historic Hideaway with King Bed & Spa-Inspired Bath

The price is NZ$1,120
includes taxes & fees
8 July - 9 July
Historic Hideaway with King Bed & Spa-Inspired Bath

A unique mountaintop getaway overlooking Willow Croft Winery.

10.0 out of 10, Exceptional, (100)
"The house was beautiful, fully stocked, close to home and vineyards. It surpassed our expectations! Can’t wait to again. "
The price is NZ$928
includes taxes & fees
8 July - 9 July
A unique mountaintop getaway overlooking Willow Croft Winery.

Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC

The price is NZ$799
includes taxes & fees
15 July - 16 July
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC

Spacious Modern Home on Middleburg Horse Farm

10.0 out of 10, Exceptional, (17)
"The house is very well designed and tastefully furnished. It is also the most thoughtfully equipped rental in which I've stayed. There was everything we needed to cook family meals and a fantastic coffee set up."
The price is NZ$694
includes taxes & fees
8 July - 9 July
Spacious Modern Home on Middleburg Horse Farm

Buckskin Manor - Historic, Pool, 66 Acre Vineyard

9.6 out of 10, Exceptional, (17)
"The house was lovely and the pool was divine !! We all had a great time and would highly recommend this place for any occasion!"
The price is NZ$1,941
includes taxes & fees
31 July - 1 Aug
Buckskin Manor - Historic, Pool, 66 Acre Vineyard

4 King Suites w/ Hot Tub, Fire Pit, Ping Pong, Arcade, Yard Games

10.0 out of 10, Exceptional, (12)
"We loved the night out at this property. A beautiful house in a great spot. The hosts were so accommodating and really friendly. "
4 King Suites w/ Hot Tub, Fire Pit, Ping Pong, Arcade, Yard Games
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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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?

Stunning Views, Riverfront Privacy, 18-Acre Estate - Near Hikes, Wine/Breweries!: This highly rated holiday home rental in Charles Town is located on a river, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games. 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 15 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 Charles Town Library 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.