Charles Town Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Charles Town holiday rentals

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.
The price is HK$1,566
HK$2,597 total
includes taxes & fees
13 May - 14 May
Antietam Creek - Quiet 2 Bedroom Cabin

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
The price is HK$1,289
HK$2,520 total
includes taxes & fees
14 May - 15 May
Cozy cabin w/hot tub & game room

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.
The price is HK$1,137
HK$2,623 total
includes taxes & fees
13 May - 14 May
Family & Pet Friendly Mountain Retreat~ Steam Shower~ 5 minutes from lake.

Cabin at the Gap | You Won't Believe the View!

Cabin at the Gap | You Won't Believe the View!
Harpers Ferry
The price is HK$783
HK$2,683 total
includes taxes & fees
25 May - 26 May
Cabin at the Gap | You Won't Believe the View!

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.
The price is HK$783
HK$1,776 total
includes taxes & fees
19 May - 20 May
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

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.
The price is HK$979
HK$2,274 total
includes taxes & fees
18 May - 19 May
Charming "Cream of the Crop" Cape ~❤️of Middletown

Leesburg Hideaway- King Bed + Private Backyard

Leesburg Hideaway- King Bed + Private Backyard
Leesburg
10.0 out of 10, Exceptional, (34 reviews)
"Adorable, comfy, private & well appointed. Well cleared of snow for our arrival after a difficult snow/ice storm. Comfortable mattress was a bonus. We enjoyed our stay! "
United States
Amy M.
The price is HK$1,304
HK$2,724 total
includes taxes & fees
20 May - 21 May
Leesburg Hideaway- King Bed + Private Backyard

Secluded cabin w/hot tub & deck, dog-friendly

Secluded cabin w/hot tub & deck, dog-friendly
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.
The price is HK$1,624
HK$2,757 total
includes taxes & fees
13 May - 14 May
Secluded cabin w/hot tub & deck, dog-friendly

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.
The price is HK$1,135
HK$1,369 total
includes taxes & fees
13 May - 14 May
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath

❤️ 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.
The price is HK$521
HK$1,057 total
includes taxes & fees
19 May - 20 May
❤️ Secluded 1940s Romantic Tiny House on the River

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.
The price is HK$1,487
HK$1,857 total
includes taxes & fees
13 May - 14 May
Blue Mountain Cabin, secluded, perfect for couples, near main road

Blue Mountain House - Hot Tub, Grill, Fire Table

Blue Mountain House - Hot Tub, Grill, Fire Table
Linden
The price is HK$1,213
HK$3,946 total
includes taxes & fees
13 May - 14 May
Blue Mountain House - Hot Tub, Grill, Fire Table

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

Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
Jefferson
9.8 out of 10, Exceptional, (63 reviews)
"The beds were incredibly comfortable. Great house. Great location. "
United States
Julie B.
The price is HK$979
HK$2,232 total
includes taxes & fees
17 May - 18 May
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

Royal Heritage Home @ Historic Leesburg

Royal Heritage Home @ Historic Leesburg
Leesburg's Old and Historic District
9.8 out of 10, Exceptional, (40 reviews)
"Great place to stay! Well decorated, equipped and spacious! Outdoor fire pit and a huge stack of firewood was a nice bonus"
United States
Steve S.
Royal Heritage Home @ Historic Leesburg

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)
"Property was beautiful, and the hot tub was amazing! We will definitely book again!"
United States
KasiLyn D.
The price is HK$1,761
HK$3,097 total
includes taxes & fees
13 May - 14 May
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!

Cozy Cabin | Lakefront, Hot Tub, Outdoor Sauna

Cozy Cabin | Lakefront, Hot Tub, Outdoor Sauna
Harpers Ferry
9.8 out of 10, Exceptional, (47 reviews)
"The house was great, clean, beautiful setting."
United States
Brandon M.
The price is HK$1,816
HK$4,241 total
includes taxes & fees
25 May - 26 May
Cozy Cabin | Lakefront, Hot Tub, Outdoor Sauna

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.
The price is HK$1,903
HK$4,025 total
includes taxes & fees
13 May - 14 May
Quaint Royal Cottage @ Historic Leesburg

Cottage w/ Hot Tub and 100-Mile Valley Views!

Cottage w/ Hot Tub and 100-Mile Valley Views!
Harpers Ferry
9.8 out of 10, Exceptional, (22 reviews)
"Great view, very secluded"
United States
Matt s.
The price is HK$783
HK$2,980 total
includes taxes & fees
27 May - 28 May
Cottage w/ Hot Tub and 100-Mile Valley Views!

Bring Your Own Boat - Meticulously restored house on the Potomac River

Bring Your Own Boat - Meticulously restored house on the Potomac River
Hedgesville
9.8 out of 10, Exceptional, (11 reviews)
"Our stay was amazing and we really enjoyed ourselves. The place was perfect and quiet and peaceful! We will be booking with them again! "
United States
Kyndal B.
The price is HK$775
HK$1,472 total
includes taxes & fees
13 May - 14 May
Bring Your Own Boat - Meticulously restored house on the Potomac River

Antietam Look Out - Incredible Sunset Views!

Antietam Look Out - Incredible Sunset Views!
Keedysville
9.8 out of 10, Exceptional, (36 reviews)
"Great communication, very clean, beautiful views!"
United States
Lorie K.
The price is HK$783
HK$2,788 total
includes taxes & fees
27 May - 28 May
Antietam Look Out - Incredible Sunset Views!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Charles Town Hotel Reviews

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 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 18 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, Hollywood Casino at Charles Town Races 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.