Charles Town Holiday Rentals

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Holiday Rentals in Charles Town

The River House

Charles Town
10.0 out of 10, Exceptional, (9)
"Excellent experience. Super clean house. Excellent location right on the river! Would definitely rent again!!"
United States
Casey W.
The price is AU$551
includes taxes & fees
13 Nov - 14 Nov
The River House

Terra Alta - Incredible River Views and Hot Tub!

Charles Town
9.6 out of 10, Exceptional, (65)
"I recommend this house for the Harpers Ferry location. Four spacious bedrooms, three bathrooms, hot tub, and games."
United States
joshua s.
The price is AU$623
includes taxes & fees
20 Nov - 21 Nov
Terra Alta - Incredible River Views and Hot Tub!

❤️ Secluded 1940s Romantic Tiny House on the River

Shepherdstown
10.0 out of 10, Exceptional, (64)
"We truly loved this location and definitely will be back!"
United States
Astrid
The price is AU$164
includes taxes & fees
17 Nov - 18 Nov
❤️ Secluded 1940s Romantic Tiny House on the River

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

Middletown
9.6 out of 10, Exceptional, (104)
"Very cute cottage, filled with rustic charm. Convenient to hiking in Catoctin and restaurants in Frederick. AC worked great on a hot weekend! No door on the bathroom, just a curtain, FYI!"
United States
Cate O.
The price is AU$350
includes taxes & fees
16 Nov - 17 Nov
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

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

Hedgesville
10.0 out of 10, Exceptional, (9)
"I booked this and Racheal warned me she was on the West Virginia side of the river... I hoped I would find a bridge across near her place but I didn't (I'm riding a bike across America). Her communication was impeccable! I only wish I could have stayed! Maybe next time! "
United States
Dan
The price is AU$251
includes taxes & fees
10 Nov - 11 Nov
Bring Your Own Boat - Meticulously restored house on the Potomac River

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

Jefferson
9.8 out of 10, Exceptional, (58)
"Very conveniently located for our visit with an amazing bakery and awesome meat market across the street. "
United States
Kathryn B.
The price is AU$367
includes taxes & fees
10 Nov - 11 Nov
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

Aslan's How - Cabin with Valley Views & Hot Tub!

2.0 star property
Harpers Ferry
9.8 out of 10, Exceptional, (8)
"This very clean, well-kept cabin was a wonderful throw-back to grandma's cabin where you would want the whole family to spend a weekend. There were only two of us, but if you have a group you won't be disappointed! The views from the deck and hot tub at sunset were spectacular. Text communication from the property management was excellent."
United States
Joan R.
The price is AU$594
includes taxes & fees
13 Nov - 14 Nov
Aslan's How - Cabin with Valley Views & Hot Tub!

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

Middletown
10.0 out of 10, Exceptional, (139)
"Lovely home Centrally located to explore historic sites/ towns Very quiet little town "
United States
M Theresa B.
The price is AU$367
includes taxes & fees
10 Nov - 11 Nov
Charming "Cream of the Crop" Cape ~❤️of Middletown

Charming Cabin in the Woods with River Access

Shepherdstown
9.6 out of 10, Exceptional, (38)
"Loved the cabin and seclusion. Would come back for sure. "
United States
Mark S.
The price is AU$397
includes taxes & fees
16 Nov - 17 Nov
Charming Cabin in the Woods with River Access

Lakefront Log Cabin w/ Dreamy Waterfront Patio!

2.0 star property
Harpers Ferry
9.6 out of 10, Exceptional, (10)
"Exactly what we expected from the listing. Nice, clean, well appointed cabin on the lake with comfortable beds. Easy check-in and check-out procedures and good communication with management. "
United States
Kimberly J.
The price is AU$515
includes taxes & fees
11 Nov - 12 Nov
Lakefront Log Cabin w/ Dreamy Waterfront Patio!

Sunny Streams Cabin - Sunset Views w/ a Hot Tub!

Keedysville
9.8 out of 10, Exceptional, (64)
"Very nice property. My family had a fun stay!"
United States
Radha V.
The price is AU$575
includes taxes & fees
17 Nov - 18 Nov
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!

Amazing dog-friendly cottage. Walk 2 Harpers Ferry

2.0 star property
Harpers Ferry
9.8 out of 10, Exceptional, (19)
"The house was beautiful and clean. All the beds were so comfortable! Kids had a lot of fun running around the huge backyard and playing croquet. We're already wanting to go back!"
United States
Abigail R.
The price is AU$477
includes taxes & fees
12 Nov - 13 Nov
Amazing dog-friendly cottage. Walk 2 Harpers Ferry

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

Front Royal
10.0 out of 10, Exceptional, (23)
"Great cabin, quiet and serene location. Highly recommended"
United States
Scott L.
The price is AU$352
includes taxes & fees
10 Nov - 11 Nov
Blue Mountain Cabin, secluded, perfect for couples, near main road

Wild Hare Cottage

Purcellville
10.0 out of 10, Exceptional, (10)
"Perfect spot to relax for a long weekend. Easy drive to Middleburg, VA, wineries, breweries, and hiking. Would stay again. "
United States
Jennifer K.
The price is AU$371
includes taxes & fees
3 Dec - 4 Dec
Wild Hare Cottage

Antietam Look Out - Incredible Sunset Views!

Keedysville
9.8 out of 10, Exceptional, (32)
"Nice property, but expensive for two nights."
United States
Sue S.
The price is AU$556
includes taxes & fees
19 Nov - 20 Nov
Antietam Look Out - Incredible Sunset Views!

Historic Hideaway

Leesburg
10.0 out of 10, Exceptional, (29)
"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! "
United States
Olivia H.
The price is AU$480
includes taxes & fees
11 Nov - 12 Nov
Historic Hideaway

Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI

Harpers Ferry
9.4 out of 10, Exceptional, (27)
"We had a great stay and the house was perfect for a quick getaway weekend for our family. Close to wineries and explored Harper’s Ferry. Communication with the host Tony was great. We would stay here again!"
United States
Samantha W.
The price is AU$557
includes taxes & fees
11 Nov - 12 Nov
Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI

Cozy Getaway near Harper's Ferry, C&O & Potomac River, Frederick & train to DC

Brunswick
9.8 out of 10, Exceptional, (52)
"Nice place. We loved all the thoughtful touches that Kim has put into the place. My sister's and I stayed in the "Cozy" cottage.Thanks for a great stay!"
United States
June H.
The price is AU$250
includes taxes & fees
10 Nov - 11 Nov
Cozy Getaway near Harper's Ferry, C&O & Potomac River, Frederick & train to DC

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

Hamilton
9.6 out of 10, Exceptional, (7)
"It was a great place to starve whole experience was perfect. "
United States
Jaime B.
The price is AU$610
includes taxes & fees
10 Nov - 11 Nov
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!

Hot Tub, Fire Pit, Deck, Grill, WiFi, Dog-Friendly

Gerrardstown
9.4 out of 10, Exceptional, (11)
"Perfect quick night away as a family! Especially enjoyed the hot tub!"
United States
Kelly L.
The price is AU$408
includes taxes & fees
11 Nov - 12 Nov
Hot Tub, Fire Pit, Deck, Grill, WiFi, Dog-Friendly
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

Find out more about Charles Town

Everything you need to know about Charles Town holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Charles Town holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Charles Town holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Charles Town holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Charles Town holiday rentals we have selected for you start as low as AU$164 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Charles Town rentals

At Expedia, we put the best Charles Town holiday 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 holiday.

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. 

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?

Modern Country House on the Shenandoah River : This highly rated holiday home rental in Charles Town is located on a river, and has a balcony, a garden 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. You and your friends and family can relax into your holiday with amenities such as a selection of games. Our travellers also rate Stunning Views, Riverfront Privacy, 18-Acre Estate - Near Hikes, Wine/Breweries! as a favourite home for rent in Charles Town.

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, Charles Town Library and Hollywood Casino at Charles Town Races 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.