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
Cabin in Charles Town
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!
22–29 Aug
₹14,853 per night
4.99 out of 5 average rating, 187 reviews
Guest favourite
Guest suite in Shepherdstown
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.
22–29 Jun
₹6,376 per night
4.96 out of 5 average rating, 561 reviews
Guest favourite
Guest suite in Summit Point
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!
1–8 Aug
₹9,215 per night
4.97 out of 5 average rating, 127 reviews

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
Farm stay in Harpers Ferry
The Lodge Room at Mt. Mama Meadows Homestead
18–25 Apr
₹10,611 per night
5.0 out of 5 average rating, 214 reviews
Guest favourite
Home in Winchester
Newly Renovated Cozy Cottage
30 Nov – 7 Dec
₹6,222 per night
4.9 out of 5 average rating, 179 reviews
Guest favourite
Home in Inwood
Arden House, Inwood WV
13–20 Nov
₹6,218 per night
4.89 out of 5 average rating, 536 reviews
Guest favourite
Guest house in Purcellville
Barn Apartment in VA Wine Country
22–29 Jul
₹5,025 per night
4.8 out of 5 average rating, 255 reviews
Guest favourite
Home in Winchester
Full basement with private entrance. Hot tub
9–14 May
₹4,975 per night
4.97 out of 5 average rating, 184 reviews
Guest favourite
Farm stay in Lovettsville
'Waterfront' on 1796 Historic Farm
19–26 Dec
₹9,949 per night
5.0 out of 5 average rating, 128 reviews
Guest favourite
Cottage in Winchester
Emma's Stone Cottage
2–9 Dec
₹8,810 per night
4.97 out of 5 average rating, 415 reviews
Guest favourite
Guest suite in Harpers Ferry
Beautiful suite, spa bathroom & gardens
8–15 Nov
₹10,713 per night
4.98 out of 5 average rating, 497 reviews
Superhost
Loft in Martinsburg
The Penthouse-Cool Vibes
26 Jan – 2 Feb
₹9,519 per night
4.9 out of 5 average rating, 108 reviews
Guest favourite
Farm stay in Harpers Ferry
La Soledad Lavender Farm on the Potomac
5–12 Oct
₹21,556 per night
5.0 out of 5 average rating, 257 reviews
Superhost
Flat in Charles Town
The Downtowner in Charles Town
14–21 Apr
₹8,054 per night
4.92 out of 5 average rating, 12 reviews
Guest favourite
Home in Charles Town
2BR w/Pool & Hottub close to Casino
4–11 Nov
₹14,418 per night
5.0 out of 5 average rating, 6 reviews

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

₹4,145 before taxes and fees

Destinations to explore