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Charles Town Holiday Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Charles Town holiday rentals

A hallway with wooden flooring, a ceiling fan, and a door leading to a room with a bed.

1. Schilling House

Schilling House
3.0 star property
Bolivar
The price is NZ$585
includes taxes & fees
5 Oct - 6 Oct
Schilling House
A bedroom with a large bed, a bench, a chair, a nightstand, and a wall with decorative plates.

2. Balcony-BBQ-Firepit-Hot tub-King-Full kitchen-TV

Balcony-BBQ-Firepit-Hot tub-King-Full kitchen-TV
Harpers Ferry
10.0 out of 10, Exceptional, (20 reviews)
"Overall good property- close location to all attractions"
United States
Trisha P.
The price is NZ$727
includes taxes & fees
24 Sept - 25 Sept
Balcony-BBQ-Firepit-Hot tub-King-Full kitchen-TV
A cylindrical metal building with a lit entrance, surrounded by trees.

3. Wild And Wonderful Silos

Wild And Wonderful Silos
Harpers Ferry
8.2 out of 10, Very good, (31 reviews)
"Cozy & Charming! Love the location! Really enjoyed our stay in the "Tiny House Silo!""
United States
Stephanie B.
The price is NZ$512
includes taxes & fees
7 Oct - 8 Oct
Wild And Wonderful Silos
A spacious room with a large dining table, white chairs, and a ceiling fan.

4. Family & Pet Friendly Mountain Cabin~ Steam Shower~ 5 minutes from lake!

Family & Pet Friendly Mountain Cabin~ Steam Shower~ 5 minutes from lake!
Harpers Ferry
10.0 out of 10, Exceptional, (104 reviews)
"It was very clean, comfortable and well supplied with everything you would need. Beautiful scenery."
United States
John B.
The price is NZ$640
includes taxes & fees
28 Sept - 29 Sept
Family & Pet Friendly Mountain Cabin~ Steam Shower~ 5 minutes from lake!
An outdoor dining area with a table set for two, surrounded by chairs, and a grill on the right.

5. New Playground•Fenced Yard•Hot Tub•King Bed•Pets

New Playground•Fenced Yard•Hot Tub•King Bed•Pets
Harpers Ferry
10.0 out of 10, Exceptional, (36 reviews)
"Host was helpful and everything was wonderful."
United States
Karen
The price is NZ$721
includes taxes & fees
24 Sept - 25 Sept
New Playground•Fenced Yard•Hot Tub•King Bed•Pets
A cozy cabin interior with a wooden interior, a sofa, a table, and a view through large windows.

6. Blue Ridge Getaway - Sunset Views, A.T. Access

Blue Ridge Getaway - Sunset Views, A.T. Access
Harpers Ferry
9.8 out of 10, Exceptional, (76 reviews)
"Great place and a great time."
United States
Katrina C.
The price is NZ$626
includes taxes & fees
24 Sept - 25 Sept
Blue Ridge Getaway - Sunset Views, A.T. Access
A wooden deck with a table and chairs, a barbecue grill, and a red umbrella.

7. 3BR cabin w/ hot tub & game room

3BR cabin w/ hot tub & game room
Harpers Ferry
9.0 out of 10, Wonderful, (67 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 NZ$604
includes taxes & fees
28 Sept - 29 Sept
3BR cabin w/ hot tub & game room
A wooden interior with a dining table set for four, a fireplace, and large windows offering a view of the outdoors.

8. Cozy Cabin | Lakefront, Hot Tub, Outdoor Sauna

Cozy Cabin | Lakefront, Hot Tub, Outdoor Sauna
Harpers Ferry
9.8 out of 10, Exceptional, (48 reviews)
"Very relaxing great time."
United States
Alfred A.
The price is NZ$789
includes taxes & fees
24 Sept - 25 Sept
Cozy Cabin | Lakefront, Hot Tub, Outdoor Sauna
A forested area with a metal railing and a paved path.

9. Mountain Cabin in the Woods, Near Wineries & More!

Mountain Cabin in the Woods, Near Wineries & More!
Harpers Ferry
8.8 out of 10, Excellent, (35 reviews)
"Scott very responsive; gave us multiple recommendations for restaurants and places to see, things to do. My kids loved the hot tub, beds were very comfortable- we had a great time!"
United States
Katie F.
The price is NZ$426
includes taxes & fees
7 Oct - 8 Oct
Mountain Cabin in the Woods, Near Wineries & More!
A cozy living room with a fireplace, wooden ceiling, and a dining area with a kitchen in the background.

10. Forest chalet w/ hot tub & BBQ grill

Forest chalet w/ hot tub & BBQ grill
Harpers Ferry
9.2 out of 10, Wonderful, (35 reviews)
"Very nice cabin. Close to Harpers Ferry. Comfortable"
United States
Dianne A.
The price is NZ$679
includes taxes & fees
5 Oct - 6 Oct
Forest chalet w/ hot tub & BBQ grill
A wooden deck with a view of a forested landscape and a sunset.

11. A peaceful, forest retreat with stunning views near historic Harpers Ferry.

A peaceful, forest retreat with stunning views near historic Harpers Ferry.
Harpers Ferry
9.0 out of 10, Wonderful, (14 reviews)
"House was clean and loaded with required amenities. We loved the backyard view and the proximity to the lakeside picnic area."
United States
henu m.
The price is NZ$677
includes taxes & fees
28 Sept - 29 Sept
A peaceful, forest retreat with stunning views near historic Harpers Ferry.
A cabin with a stone fire pit and white Adirondack chairs, surrounded by trees and a view of the sunset.

12. Rebels Rest - Cabin with Enchanting Sunset Views!

Rebels Rest - Cabin with Enchanting Sunset Views!
Harpers Ferry
9.8 out of 10, Exceptional, (42 reviews)
"Enjoyed our visit. House was well-appointed and had an amazing view from back deck."
United States
Kathy V.
The price is NZ$733
includes taxes & fees
24 Sept - 25 Sept
Rebels Rest - Cabin with Enchanting Sunset Views!
A sign for Antietam National Battlefield, part of the National Park Service, with a stone wall and flowers in the foreground.

13. Peaceful Single-Level Retreat, Near Harpers Ferry, Easy Access + Prime Location

Peaceful Single-Level Retreat, Near Harpers Ferry, Easy Access + Prime Location
Harpers Ferry
7.4 out of 10, Good, (28 reviews)
"The inside was well done and clean. Even though the neighbors are close, they were quiet. My husband and I were able to relax in a comfortable setting."
United States
Melissa H.
The price is NZ$609
includes taxes & fees
13 Oct - 14 Oct
Peaceful Single-Level Retreat, Near Harpers Ferry, Easy Access + Prime Location
A covered outdoor area with wicker furniture, a ceiling fan, and a view of a lake and forest.

14. Peaceful Lakefront Cottage with Mountain Views!

Peaceful Lakefront Cottage with Mountain Views!
Harpers Ferry
9.8 out of 10, Exceptional, (40 reviews)
"Clean house. Host was able to accessible. Hot tub worked and clean. Kitchen had everything we needed. Great place to stay and relax"
United States
Lisa h.
The price is NZ$853
includes taxes & fees
24 Sept - 25 Sept
Peaceful Lakefront Cottage with Mountain Views!
A room with a large window overlooking a forested area.

15. Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!

Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!
Harpers Ferry
9.8 out of 10, Exceptional, (21 reviews)
"We had a wonderful stay. The communication and the guestbook were wonderful. The view was gorgeous and the property was clean and comfortable. "
United States
Kaitlyn C.
The price is NZ$685
includes taxes & fees
24 Sept - 25 Sept
Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!
A modern kitchen with stainless steel appliances, a dining area with a round table, and a spiral staircase leading to a living area with a sofa and a coffee table.

16. Amazing dog-friendly cottage. Walk 2 Harpers Ferry

Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Harpers Ferry
9.8 out of 10, Exceptional, (33 reviews)
"We enjoyed our stay here so much and when we go back to Harper’s Ferry we hope to stay in the same place again"
United States
Zachary S.
The price is NZ$635
includes taxes & fees
27 Sept - 28 Sept
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
A hot tub outside a building with a view of autumn trees.

17. Woodsy Retreat with a Hot Tub and Seasonal Views!

Woodsy Retreat with a Hot Tub and Seasonal Views!
Harpers Ferry
9.8 out of 10, Exceptional, (28 reviews)
"Great house. Comfortable beds, had everything we needed. Loved the hot tube and wood burner. "
United States
Amy P.
The price is NZ$585
includes taxes & fees
24 Sept - 25 Sept
Woodsy Retreat with a Hot Tub and Seasonal Views!
A hot tub with a view of a forested landscape during sunset.

18. 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, (27 reviews)
"The property was so nice with a beautiful view. We had a great time! Highly recommend this property."
United States
Anonymous traveller
The price is NZ$758
includes taxes & fees
12 Oct - 13 Oct
Cottage w/ Hot Tub and 100-Mile Valley Views!
A spacious dining area with a wooden table and chairs, large windows with a view of trees, and a stone wall in the background.

19. Stone Cabin on Valley View: Fire Pit + Hot Tub

Stone Cabin on Valley View: Fire Pit + Hot Tub
Harpers Ferry
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful scenery! Beautiful home! Wonderful hosts!"
United States
Brian S.
The price is NZ$708
includes taxes & fees
6 Oct - 7 Oct
Stone Cabin on Valley View: Fire Pit + Hot Tub
A modern kitchen with a central island, stainless steel appliances, and a stone accent wall.

20. Brand new home in Historic Harpers Ferry - Barrel Sauna - Fire Pit - Luxury!

Brand new home in Historic Harpers Ferry - Barrel Sauna - Fire Pit - Luxury!
Harpers Ferry
10.0 out of 10, Exceptional, (15 reviews)
"Beautiful home. Very attentive hosts, great location. We enjoyed every minute at this home. "
United States
Katrina
The price is NZ$936
includes taxes & fees
7 Oct - 8 Oct
Brand new home in Historic Harpers Ferry - Barrel Sauna - Fire Pit - Luxury!
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

Quality Inn Winchester

Quality Inn Winchester

8/10 Good
"Location was very convenient and included inside access to 24hr Denny’s. Parking lot adjacent to an Exxon. Hot breakfast, hard boiled eggs, English"
Joanne 1-night trip
Posted 7 hours ago
Quality Inn Winchester

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 favorite 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 depends 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 NZ$183 per night. Entering your travel dates in the search wizard you might find 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?

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 Charles Town Home w/ Private Pool & Hot Tub as a favourite home for rent in Charles Town.

How many holiday rentals will I find in Charles Town?

Choose from 14 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.