Charles Town Vacation Rentals

Check prices for these dates

In two weeks
May 22 - May 24
In two months
Jul 3 - Jul 5
In three months
Jul 31 - Aug 2
In four months
Aug 28 - Aug 30

Our top choices for Charles Town vacation rentals

Property grounds

Terra Alta - Incredible River Views and Hot Tub!

Terra Alta - Incredible River Views and Hot Tub!
Charles Town
9.6 out of 10, Exceptional, (70 reviews)
"Nice quiet view, able to sit on deck for hours and talk. Close to restaurants, and stores. Had a great stay."
United States
Paul M.
Terra Alta - Incredible River Views and Hot Tub!
Terrace/patio

Skyline Yurt: Hot Tub~Wood Stove~WiFi~EVcharger

Skyline Yurt: Hot Tub~Wood Stove~WiFi~EVcharger
Front Royal
9.8 out of 10, Exceptional, (8 reviews)
"Unique accommodation overlooking a beautiful valley with many convenient modern features such as a EV charger provider"
United States
Paul S.
$493 nightly
The price is $544
May 26 - May 27
Total with taxes and fees
Skyline Yurt: Hot Tub~Wood Stove~WiFi~EVcharger
Interior

Antietam Creek - Quiet 2 Bedroom Cabin

Antietam Creek - Quiet 2 Bedroom Cabin
Keedysville
9.2 out of 10, Wonderful, (89 reviews)
"Did a small girls night here and we had the best time! Out there and quiet for a get away and plenty to do inside for colder weather we loved the bookshelf full of board games and books and the piano to tinker around on! The gas fireplace kept the whole place cranking with heat no problems Definitely would stay here again!"
United States
Kandy T.
$310 nightly
The price is $329
May 11 - May 12
Total with taxes and fees
Antietam Creek - Quiet 2 Bedroom Cabin
Property grounds

Charming Cabin in the Woods with River Access

Charming Cabin in the Woods with River Access
Shepherdstown
9.6 out of 10, Exceptional, (44 reviews)
"Loved the place and area."
United States
Steve R.
$304 nightly
The price is $339
May 25 - May 26
Total with taxes and fees
Charming Cabin in the Woods with River Access
Exterior

18th Century Stone Cottage minutes from historic Middleburg

18th Century Stone Cottage minutes from historic Middleburg
Middleburg
10.0 out of 10, Exceptional, (58 reviews)
"Loved out stay! "
United States
Emilee
$367 nightly
The price is $394
May 10 - May 11
Total with taxes and fees
18th Century Stone Cottage minutes from historic Middleburg
Interior

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

Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Middletown
9.6 out of 10, Exceptional, (114 reviews)
"Good stay. Would visit again. "
United States
Lonnie F.
$186 nightly
The price is $197
May 10 - May 11
Total with taxes and fees
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Interior

The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!

The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Hamilton
9.8 out of 10, Exceptional, (16 reviews)
"Absolutely amazing place and stay! I could not possibly be more impressed and I look forward to coming back."
United States
Jasmine M.
$347 nightly
The price is $396
May 10 - May 11
Total with taxes and fees
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Exterior

Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath

Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
Sharpsburg
9.6 out of 10, Exceptional, (200 reviews)
"We enjoyed our stay and the location was excellent"
United States
Barbara W.
$165 nightly
The price is $175
May 10 - May 11
Total with taxes and fees
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
Dining

Family & Pet Friendly Mountain Retreat~ Steam Shower~ 5 minutes from lake.

Family & Pet Friendly Mountain Retreat~ Steam Shower~ 5 minutes from lake.
Harpers Ferry
10.0 out of 10, Exceptional, (88 reviews)
"The host had great communication and the place was exactly as pictured! "
United States
Colleen J.
$298 nightly
The price is $332
May 11 - May 12
Total with taxes and fees
Family & Pet Friendly Mountain Retreat~ Steam Shower~ 5 minutes from lake.
Smart TV, books, computer monitors

Leesburg Hideaway- King Bed + Private Backyard

Leesburg Hideaway- King Bed + Private Backyard
Leesburg
10.0 out of 10, Exceptional, (34 reviews)
"The host was great in communicating check in and check out instructions! We appreciated being able to park in the driveway and the fenced in back yard was also a nice amenity. Would definitely stay here again!"
United States
Katherine s.
$304 nightly
The price is $349
May 20 - May 21
Total with taxes and fees
Leesburg Hideaway- King Bed + Private Backyard
Property grounds

Blue Mountain Cabin, secluded, perfect for couples, near main road

Blue Mountain Cabin, secluded, perfect for couples, near main road
Front Royal
10.0 out of 10, Exceptional, (34 reviews)
"Great stay! The place was clean, comfortable, and exactly as described. Host was responsive and helpful. Would definitely stay again."
United States
Wafaa L.
$213 nightly
The price is $235
May 10 - May 11
Total with taxes and fees
Blue Mountain Cabin, secluded, perfect for couples, near main road
Outdoor dining

Cozy cabin w/hot tub & game room

Cozy cabin w/hot tub & game room
Harpers Ferry
9.0 out of 10, Wonderful, (65 reviews)
"House was wonderful, and I loved how often Tony checked in! Will absolutely be staying here again!"
United States
Chelsey-Ann
$309 nightly
The price is $322
May 10 - May 11
Total with taxes and fees
Cozy cabin w/hot tub & game room
Exterior

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

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (145 reviews)
"Love the place will book again"
United States
WAYNE M.
$237 nightly
The price is $251
May 10 - May 11
Total with taxes and fees
Charming "Cream of the Crop" Cape ~❤️of Middletown
TV, fireplace, offices

Blue Mountain House - Hot Tub, Grill, Fire Table

Blue Mountain House - Hot Tub, Grill, Fire Table
Linden
$457 nightly
The price is $504
May 10 - May 11
Total with taxes and fees
Blue Mountain House - Hot Tub, Grill, Fire Table
Fridge, microwave, oven, stovetop

Quaint Royal Cottage @ Historic Leesburg

Quaint Royal Cottage @ Historic Leesburg
Leesburg's Old and Historic District
10.0 out of 10, Exceptional, (11 reviews)
"Great location in a great town!"
United States
Gigi D.
$431 nightly
The price is $495
May 11 - May 12
Total with taxes and fees
Quaint Royal Cottage @ Historic Leesburg
Interior

Secluded cabin w/hot tub & deck

Secluded cabin w/hot tub & deck
Harpers Ferry
9.2 out of 10, Wonderful, (33 reviews)
"Enjoyed the levels, hot tub, porch to get outside with my coffee, pet strolling area marvelous and washer/dryer."
United States
tracey b.
$323 nightly
The price is $349
May 10 - May 11
Total with taxes and fees
Secluded cabin w/hot tub & deck
Exterior

❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.8 out of 10, Exceptional, (74 reviews)
"Cozy home, great location, and kind and helpful host. Would like to stay again. "
United States
Matthew S.
$122 nightly
The price is $135
May 19 - May 20
Total with taxes and fees
❤️ Secluded 1940s Romantic Tiny House on the River
Property grounds

Cozy w/Fire Pit, Grill, Screened Porch & WiFi

Cozy w/Fire Pit, Grill, Screened Porch & WiFi
Harpers Ferry
10.0 out of 10, Exceptional, (3 reviews)
"The host was very communicative and the place was very clean. "
United States
Christopher M.
$281 nightly
The price is $302
May 10 - May 11
Total with taxes and fees
Cozy w/Fire Pit, Grill, Screened Porch & WiFi
Microwave, oven, stovetop, dishwasher

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

Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
Rohrersville
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful historic home. Hosts were very welcoming and the place was newly renovated. "
United States
Drew M.
$429 nightly
The price is $455
May 18 - May 19
Total with taxes and fees
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
Exterior

Cottage on King | Charming Historic Leesburg Home

Cottage on King | Charming Historic Leesburg Home
Leesburg's Old and Historic District
9.6 out of 10, Exceptional, (70 reviews)
"Great location and very comfortable house. Beautiful place to stay, we loved sitting on the porch in the morning with coffee"
United States
Fern
$372 nightly
The price is $428
May 12 - May 13
Total with taxes and fees
Cottage on King | Charming Historic Leesburg Home
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

Spark by Hilton Winchester

Spark by Hilton Winchester

10/10 Excellent
"It was a nice hotel and very worth the price we paid! The Continental breakfast was great and had a lot of choices. The staff was very attentive as well."
Cynthia 1-night trip
Posted 4 hours ago
Spark by Hilton Winchester

Find out more about Charles Town

Everything you need to know about Charles Town vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Charles Town vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Charles Town vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Charles Town vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Charles Town. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Charles Town in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $135 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Charles Town rentals

At Expedia, we put the best Charles Town vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Charles Town rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Charles Town vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Charles Town. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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?

Terra Alta - Incredible River Views and Hot Tub!: This Charles Town vacation home rental is located on a river and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. It offers a private yard, a selection of games, and a hot tub so you can immerse yourself in your vacation. Our travelers also rate Modern Country House on the Shenandoah River as a favorite home for rent in Charles Town.

How many vacation rentals will I find in Charles Town?

Choose from 18 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, Hollywood Casino at Charles Town Races 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.