Holiday rentals in Charles Town

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Top-rated holiday rentals in Charles Town

Guests agree: these stays are highly rated for location, cleanliness and more.

Guest favourite

Guest suite in Shepherdstown

4.96 out of 5 average rating, 563 reviews

Historic Scrabble, Shepherdstown

The perfect private guest cottage situated beside a beautiful historic home in the unique community of Scrabble Unincorporated just a half-mile from the Potomac River. Modern, comfortable and tastefully decorated with full amenities and parklike surroundings with an abundance of nature at your doorstep. Close to Shepherdstown / Shepherd Univeristy (12 minutes), Martinsburg (20 minutes), Harpers Ferry (20 minutes) and in the heart of civil war history including the famed Antietam National Park.

27 Jun – 4 Jul

₹7,753 per night
Guest favourite

Cabin in Charles Town

4.99 out of 5 average rating, 186 reviews

Vintage Riverfront Log Cabin “Emma” w/hot tub

“Emma” is a Shenandoah Riverfront Log Cabin hand built in 1900’ , she was just newly renovated. Come, Relax, you are on “River Time”. From the front porch, stroll through the yard, and across the road, you access the Shenandoah riverfront dock. Here, the river is wide, and the view is amazing, launch a kayak or tube, fish from the dock. Enjoy your evenings around the campfire. From the cabin, you are just a few minutes away from Historic Harpers Ferry, wineries and breweries. Enjoy!

28 Aug – 4 Sep

₹17,862 per night
Guest favourite

Guest suite in Summit Point

4.97 out of 5 average rating, 126 reviews

The Big Room - Historic Schoolhouse

Located one mile from the racetrack in the little village of Summit Point. This is a large renovated former classroom with 13' ceilings in the old Elementary School. Summit Point is a quiet place where you can take a leisurely stroll. There are even a couple sidewalks ;) We have 3 churches and a post office. The "Railside Market" serves food and sundries one block away. (currently has limited hours) Multiple food options are available in nearby Charles Town and lots more in Winchester Virginia!

11–18 Feb

₹10,701 per night

Popular amenities for Charles Town holiday rentals

Stay near Charles Town's top sights

Hollywood Casino at Charles Town Races110 locals recommend
Mountain View Diner8 locals recommend
Charlestown Races And Slots5 locals recommend
Alfredo's Mediterranean Grille and Steakhouse17 locals recommend
Paddy's15 locals recommend
Abolitionist Ale Works32 locals recommend

Other great holiday rentals in Charles Town

Guest favourite

Home in Winchester

4.9 out of 5 average rating, 180 reviews

Newly Renovated Cozy Cottage

3–10 Feb

₹7,222 per night
Guest favourite

Farm stay in Lovettsville

5.0 out of 5 average rating, 129 reviews

'Waterfront' on 1796 Historic Farm

25 Jun – 2 Jul

₹11,540 per night
Guest favourite

Home in Harpers Ferry

4.94 out of 5 average rating, 509 reviews

Eclectic & Romantic - Walk to Historic Downtown!

30 Oct – 6 Nov

₹14,507 per night
Guest favourite

Farm stay in Round Hill

4.94 out of 5 average rating, 340 reviews

Come and get your goat on!

22–29 Jun

₹12,821 per night
Guest favourite

Flat in Shenandoah Junction

4.91 out of 5 average rating, 181 reviews

Private apt near Shepherdstown

20–27 Jul

₹7,085 per night
Guest favourite

Home in Inwood

4.89 out of 5 average rating, 539 reviews

Arden House, Inwood WV

23–30 Nov

₹7,134 per night
Guest favourite

Treehouse in Shepherdstown

4.97 out of 5 average rating, 243 reviews

Cozy West Virginia Treehouse

9–16 Jun

₹12,664 per night
Guest favourite

Cottage in Harpers Ferry

4.93 out of 5 average rating, 499 reviews

The Carriage House at Carrot Top Cottage

26 Aug – 2 Sep

₹9,292 per night
Guest favourite

Guest house in Round Hill

4.98 out of 5 average rating, 371 reviews

Private Carriage House

23–30 May

₹11,056 per night
Superhost

Flat in Charles Town

4.78 out of 5 average rating, 32 reviews

The Uptowner in Charles Town near Harpers Ferry

12–19 Apr

₹7,849 per night
Guest favourite

Loft in Charles Town

5.0 out of 5 average rating, 38 reviews

Quaint 1 Bedroom Country Get-A-Way

6–13 Oct

₹10,653 per night
Guest favourite

Cabin in Charles Town

4.91 out of 5 average rating, 77 reviews

The River House

13–20 Jul

₹13,008 per night

Quick stats about holiday rentals in Charles Town

Total rentals

30 properties

Wifi availability

30 properties include access to wifi

Rentals with dedicated workspaces

10 properties have a dedicated workspace

Family-friendly rentals

20 properties are a good fit for families

Total number of reviews

1.9T reviews

Nightly prices starting at

₹4,167 before taxes and fees

Destinations to explore