Vacation rentals in Charles Town

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Top-rated vacation rentals in Charles Town

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Guest favourite

Guest suite in Summit Point

4.97 out of 5 average rating, 131 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!

Apr. 16 – 23

$204 CAD per night

Guest favourite

Cottage in Harpers Ferry

4.94 out of 5 average rating, 244 reviews

Adorable apartment with a view

This private apartment has it all. A bright, clean space with comforts of home. Great views! In addition you are centrally located to many attractions and destinations. These include the Appalachian Trail, Harpers Ferry National Park, white water rafting, Hollywood Casino, Charleston Race Track, fishing, River Riders Family Adventure, tour bus ride, shopping outlets, antique shopping, glass outlet, Skyline and Luray caverns, glass outlet, close to train station for day trips to DC, and more.

May 27 – Jun. 3

$198 CAD per night

Guest favourite

Farm stay in Round Hill

4.94 out of 5 average rating, 350 reviews

Come and get your goat on!

Nestled at the base of the Blue Ridge and tucked away in the woods, we offer a quiet and peaceful get away while being convenient to tons. Enjoy the peace of 13-acres of woodlands and pasture. A large private deck provides a plenty sun with pasture and woodlands views with some great star watching at night. Miles of walking, the Appalachian trail, fantastic cycling; historic towns and places; wineries, breweries, and distilleries; Potomac and Shenandoah rivers. All just minutes away.

Sep. 2 – 9

$204 CAD per night

Guest favourite

Apartment in Shenandoah Junction

4.91 out of 5 average rating, 188 reviews

Private apt near Shepherdstown

A Little Respite is our private 1 bedroom apt *King size bed *Queen size pullout sofa *7 min from Shepherdstown, 15 min from Harpers Ferry *self check-in *full kitchen *fast Wi-Fi & Roku channels *magnetic chargers *Alexa alarm clock/sound machine *quiet *fire-pit and gas grill *ideal rustic family retreat *getaway for outdoor enthusiasts, bikers, hikers, and paddlers *remote work & business traveler friendly *2 miles from Marc commuter train *Weekly and monthly stays welcome

Jan. 19 – 26

$126 CAD per night

Guest favourite

Home in Bolivar

4.96 out of 5 average rating, 185 reviews

Newly renovated - Walk to Harpers Ferry NP

Kick back and relax in this newly interior renovated space on the corner lot of a very quiet neighborhood. It has 800 sq feet with full kitchen, living area, bath, remote work desktop with an ergonomic chair, deck, large fenced in yard, and a 24/7 convenience store one block away. It has a one bedroom with a Dream Cloud queen mattress on an adjustable bed. Located between Bolivar Heights NP and downtown Harpers Ferry. Please note that the living area for this home is upstairs.

Sep. 4 – 11

$189 CAD per night

Guest favourite

Cottage in Winchester

4.97 out of 5 average rating, 425 reviews

Emma's Stone Cottage

Relax and unwind in the privacy of this wonderful stone cottage, which sits on 15 beautiful acres. In addition, it is located only 2.5 miles from I-81 and 14 minutes from Winchester Medical Center, Old Town Winchester, Shenandoah University and much more. Our cottage is fully furnished with all the comforts of home. From the full kitchen, central air, water softener, HD smart televisions, Wifi, outdoor firepit and more. It has everything you need for a peaceful and enjoyable stay.

Dec. 12 – 19

$201 CAD per night

Guest favourite

Farm stay in Harpers Ferry

5.0 out of 5 average rating, 225 reviews

The Lodge Room at Mt. Mama Meadows Homestead

This listing is adults only. Mt. Mama Meadows Homestead is our own slice of “almost Heaven”. We're located in Harpers Ferry, a small historic town in Jefferson County, West Virginia, in the lower Shenandoah Valley. Whether you are coming to check out the surrounding Blue Ridge Mountains, hike the Appalachian Trail, raft the Potomac or Shenandoah rivers, delve into the rich Civil War history of the area, or just relax on the homestead, there is no shortage of things to do.

Jun. 22 – 29

$231 CAD per night

Guest favourite

Guest suite in Harpers Ferry

4.98 out of 5 average rating, 510 reviews

Beautiful suite, spa bathroom & gardens

Private-entry luxurious suite combining comfort & style for a memorable stay. Located in quiet neighborhood -- Harpers Ferry historic district -- 1920s stone foursquare home with beautiful gardens to explore. Close to National Park, Potomac & Shenandoah Rivers, C&O Canal Trail, AT, Amtrak train station, Storer College, & Loudoun Co. wineries. An ideal accommodation for a romantic couple's getaway. More pics on Insta @rockhavenbnb

Nov. 7 – 14

$238 CAD per night

Guest favourite

Guest suite in Harpers Ferry

4.99 out of 5 average rating, 194 reviews

Luxury Mountain Getaway: Hiking, Wines & Sunsets

Celebrate your special moment in chic elegance and 5-star amenities for adult couples only. You deserve the SunsetRouge. It's a destination in a relaxed and romantic setting to escape anxiety of kids, city, and work. Let the fun décor and panoramic views inspire the writer and artist within. During the day, take flight with eagles at eye level. At night, gaze into the heaven to catch a falling star.

Jan. 23 – 28

$470 CAD per night

Superhost

Loft in Martinsburg

4.9 out of 5 average rating, 113 reviews

The Penthouse-Cool Vibes

Imagine being downtown near the restaurants, bars, and shopping. Go up 2 flights of stairs and you've arrived in heaven. The breathtaking views from the top floor is memorable. You'll love the light that spreads out through the huge windows! Enjoy the huge king size bed or just hang out in the comfy living room. You are going to make your friends so jealous when they see your pictures!

Nov. 7 – 14

$218 CAD per night

Guest favourite

Cottage in Shepherdstown

4.96 out of 5 average rating, 186 reviews

The GW Hollida Cottage of Shepherdstown

Let time slow just a bit at this unique and tranquil getaway! This recently renovated cottage is situated just behind the GW Hollida house, circa early 1800s. Whether taking a few extra breaths of fresh air on the deck, taking a stroll through the 5 acres of serenity, or kicking back to enjoy some peace and quiet, we are confident you'll love this place as much as we do!

Apr. 11 – 18

$185 CAD per night

Guest favourite

Cabin in Shepherdstown

4.95 out of 5 average rating, 423 reviews

The Log Cabin

A restored 1700's log cabin in a convenient location to Shepherdstown and surrounding attractions. One bedroom upstairs with a queen sized bed. One pull out sofa in the downstairs living area. In the summer of 2018, we have added an intimate brick patio area suitable for alfresco dining and for fireside sitting. It is peaceful. It is beautiful. You will not want to leave.

Oct. 23 – 30

$172 CAD per night