Charles Town Holiday Rentals

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Holiday Rentals in Charles Town

Modern Country House on the Shenandoah River

9.8 out of 10, Exceptional, (35)
"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

Charles Town Home w/ Private Pool & Hot Tub

10.0 out of 10, Exceptional, (52)
"This is our third year staying in this house and we love it. The company accommodates our requests and is quick to respond if we need anything. The house itself is laid out perfectly for what we need with lots of rooms for both kids and adults. "
Charles Town Home w/ Private Pool & Hot Tub

Terra Alta - Incredible River Views and Hot Tub!

9.8 out of 10, Exceptional, (57)
"We had a great time! The house overlooks the river and we loved the hot tub and fire pit! "
The price is AU$629
includes taxes & fees
21 Aug - 22 Aug
Terra Alta - Incredible River Views and Hot Tub!

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

10.0 out of 10, Exceptional, (20)
"Great stay for two young families. Lovely home and great location. Would recommend for a group trip to the area."
Stunning Views, Riverfront Privacy, 18-Acre Estate - Near Hikes, Wine/Breweries!

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

10.0 out of 10, Exceptional, (126)
"Spectacular location. Charming and comfortable. The steps can be a challenge but are worth the effort."
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!

Breathtaking View with an Indoor Pool

9.8 out of 10, Exceptional, (256)
"We really enjoyed our stay at Bear Chase Manor! Amazing property, great pool, in a beautiful area. We are already discussing possible future visits! "
Breathtaking View with an Indoor Pool

Whiskey Hill Cabin a Mountain escape in Virginia Wine country.

10.0 out of 10, Exceptional, (90)
"This beautiful cabin has everything you need for a wonderful stay. My husband and I stayed here for our 44th anniversary while visiting local wineries. It was a perfect location."
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.

Cottage on King | Charming Historic Leesburg Home

9.6 out of 10, Exceptional, (54)
"Walkable to downtown historic Leesburg. Clean and super cute little house. Would stay again! "
The price is AU$456
includes taxes & fees
4 Aug - 5 Aug
Cottage on King | Charming Historic Leesburg Home

Charming Cabin in the Woods with River Access

9.8 out of 10, Exceptional, (28)
"Very nice rest time…"
The price is AU$498
includes taxes & fees
23 Aug - 24 Aug
Charming Cabin in the Woods with River Access

Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry

9.4 out of 10, Exceptional, (6)
The price is AU$308
includes taxes & fees
11 Aug - 12 Aug
Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry

RIVERKEEPER INN, Waterfront Property on the Potomac River

9.2 out of 10, Wonderful, (124)
"Riverkeeper Inn is located in a peaceful and quiet area of Harpers Ferry, equally perfect in early mornings and late nights. The check-in and check-out process were very easy, and the property itself had everything we could've asked for, and then some."
RIVERKEEPER INN, Waterfront Property on the Potomac River

Historical cottage in the town of Paris

9.8 out of 10, Exceptional, (45)
"This is a nice home near sky meadow park. A great place to see the stars... Very close to DC. "
Historical cottage in the town of Paris

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

9.4 out of 10, Exceptional, (3)
"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...
Charming 2-Bedroom Basement Apartment with AC, WiFi in enchanting Leesburg

Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.

10.0 out of 10, Exceptional, (137)
"Wonderful house for a great weekend away"
The price is AU$656
includes taxes & fees
10 Aug - 11 Aug
Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.

Amazing dog-friendly cottage. Walk 2 Harpers Ferry

2.0 star property
9.8 out of 10, Exceptional, (15)
"Very nice property with convenient location! Within walking distance of down town. "
The price is AU$502
includes taxes & fees
13 Aug - 14 Aug
Amazing dog-friendly cottage. Walk 2 Harpers Ferry

Historic Boonsboro Vacation Rental w/ Grill

9.2 out of 10, Wonderful, (15)
"It was perfect. Near my son’s school at Shepherd University and close to all the historic sites of Harper’s Ferry and Antietam."
Historic Boonsboro Vacation Rental w/ Grill

Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

9.8 out of 10, Exceptional, (98)
"Our stay was great and really enjoyed the house. We had so much space to have our own time and then still be able to come together for meals and hanging in the hot tub. We now want to come back in the winter and go to the sledding hill right in front of the house! "
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

❤️ Secluded 1940s Romantic Tiny House on the River

10.0 out of 10, Exceptional, (57)
"We truly loved this location and definitely will be back!"
The price is AU$224
includes taxes & fees
1 Sept - 2 Sept
❤️ Secluded 1940s Romantic Tiny House on the River

Modern cabin at the woods resort with 3-Bedroom, 2F-bath, Central Air/Heat

9.8 out of 10, Exceptional, (15)
"I loved the place, and it’s something I would rent again "
Modern cabin at the woods resort with 3-Bedroom, 2F-bath, Central Air/Heat

Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

9.6 out of 10, Exceptional, (99)
"Our weekend cabin stay was wonderful. The safe neighborhood was quite and peaceful. Its location near nature and the city was just perfect. The cozy cabin was clean and comfy. We loved Gambrill State Park and downtown Frederick didn't disappoint as well."
The price is AU$298
includes taxes & fees
7 Aug - 8 Aug
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
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

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?

Charles Town Home w/ Private Pool & Hot Tub: This highly rated holiday home rental in Charles Town offers a fireplace, a patio and air conditioning to help you feel perfectly comfortable 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. You can relax into your holiday with a selection of games and 1 hot tub. Other favourite homes for rent in Charles Town are Stunning Views, Riverfront Privacy, 18-Acre Estate - Near Hikes, Wine/Breweries! and Terra Alta - Incredible River Views and Hot Tub!.

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 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.