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Vacation rentals in Charles Town

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Top-rated vacation rentals in Charles Town

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Cabin in Charles Town

4.97 out of 5 average rating, 209 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 the yard, and across the road, to 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, breweries, hiking trails Enjoy!

Tiny home in Shepherdstown

4.99 out of 5 average rating, 119 reviews

Studio: Downtown Hideaway & Waterside Garden Oasis

Our modern studio is on the Town Run and steps away from downtown Shepherdstown. Whether you’re here for a relaxing escape or a university visit, listen to a waterfall from our cozy, zen, spa-like space with outdoor gardens. It’s an oasis with a comfortable full bed, dedicated work area, and walk-in shower. Nestled in historic downtown, you can easily explore German St., with a variety of dining options, shopping, and outdoor activities a short walk away from the Potomac River and C&O tow path.

Guest suite in Summit Point

4.97 out of 5 average rating, 151 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!

Bungalow in Great Cacapon

4.9 out of 5 average rating, 512 reviews

Rooster Wrest in the Trees

Sweet 2 bedroom bungalow. Cozy, ideal for lovers, or a quiet beautiful somewhat rustic retreat environment. Rooster has 1 full bath. Living room with satellite TV, Netflix; wood burning stove fireplace, wood provided, fully equipped kitchen, dining table, linens and starter paper goods furnished. Large deck and screen porch looking out on Cacapon Mountain. Hot tub off master bedroom deck in trees, feels like a tree house. Many mornings mist rises up from river, half mile away as crow flies.

Home in Bolivar

4.96 out of 5 average rating, 237 reviews

Newly renovated - Walk to Harpers Ferry NP

This stylish apt with fenced yard is located just mins to the HFNP Park. 24/7 convenient store just 1 block away; library across the street; a corner lot in a very quiet neighborhood. Perfect place to start your hikes or just to rest for the weekend. The home has 1 BR, kitchen, full bath and coffee bar - Keurig; coffee pot; coffee press; pour over coffee; beans and grinder; teas bags w/ water pot and private parking for our guests. Please note that the living area for this home is upstairs.

Cabin in High View

4.97 out of 5 average rating, 104 reviews

Mary's Cabin

Nestled on 2 acres in the woods of West Virginia, kick back and relax in this quiet, chic cabin. Soak in the oversized copper tub, read on the porch swing, or cuddle by the electric fireplace. All the amenities of home, but away from the hustle and bustle of daily life. Only 25 minutes to quaint Old Town Winchester, where there are unique shops, breweries, restaurants and history! The cabin is located 20 minutes from a variety of scenic hiking trails that provide opportunities for adventure.

Guest suite in Harpers Ferry

4.98 out of 5 average rating, 558 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

Guest suite in Harpers Ferry

5 out of 5 average rating, 227 reviews

Luxury Mountain Getaway: Hikes, Wineries & 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.

Home in Harpers Ferry

4.93 out of 5 average rating, 595 reviews

Eclectic & Romantic - Walk to Historic Downtown!

Eclectic space full of little treasures I’ve picked up during my travels. You will find the place cozy enough for a reset and recharge weekend but also inspiring for gatherings and celebrations. Take advantage of the books, games and excellent SONOS system in the house as well as outside on the patio. This place is great for music lovers and people who enjoy a change from the ordinary.

Cottage in Shepherdstown

4.95 out of 5 average rating, 246 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!

Cabin in Shepherdstown

4.95 out of 5 average rating, 451 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.

Cottage in Martinsburg

4.98 out of 5 average rating, 386 reviews

Last Rodeo Cottage

Our cottage is private where guest can relax; Looking to spend some quiet time out of the city. Close to D.C.and the Historic site of surrounding areas. Close to Charlestown Casinos. Our home is right off I- 81 This cottage is Handicap accessible from private parking to shower and amenities. Lovely park like setting shared with our family pets.

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Popular amenities for Charles Town vacation rentals

Free parking on premises

Air conditioning

Stay near Charles Town's top sights

Hollywood Casino at Charles Town Races110 locals recommend

Abolitionist Ale Works32 locals recommend

Walmart Supercenter30 locals recommend

ALDI21 locals recommend

Sumittra Thai Kitchen & Bar21 locals recommend

Alfredo's Mediterranean Grille and Steakhouse17 locals recommend

Other great vacation rentals in Charles Town

Cabin in Charles Town

4.93 out of 5 average rating, 99 reviews

The River House

Home in Ranson

4.9 out of 5 average rating, 20 reviews

Cozy Vintage Home by Charles Town, Casino & More!

Home in Charles Town

5 out of 5 average rating, 17 reviews

Shenandoah River House Retreat

Cabin in Harpers Ferry

4.91 out of 5 average rating, 11 reviews

A-Frame Cabin in Harpers Ferry

Vacation home in Martinsburg

4.96 out of 5 average rating, 45 reviews

The Train Station Lodge

Loft in Charles Town

5 out of 5 average rating, 41 reviews

Quaint 1 Bedroom Country Get-A-Way

Guest suite in Harpers Ferry

4.98 out of 5 average rating, 81 reviews

Tequila Sunset, Harpers Ferry. Entire first floor!

Vacation home in Charles Town

4.95 out of 5 average rating, 79 reviews

Mountain Ferry Landing - Riverfront Access

Quick stats about vacation rentals in Charles Town

Total rentals
30 properties
Nightly prices starting at
G$12,518 GYD before taxes and fees
Total number of reviews
2.2K reviews
Family-friendly rentals
20 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Charles Town?
Yes! Work meets play with ease at over 10 vacation rentals in Charles Town featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Charles Town have wifi?
Absolutely! We offer over 10 house rentals with wifi in Charles Town. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Charles Town?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with free parking, over 10 homes with wifi, over 10 homes with a kitchen, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Charles Town have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Charles Town. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Charles Town?
Charles Town has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Charles Town have a kitchen?
Absolutely! We offer over 10 house rentals with a kitchen in Charles Town. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Charles Town have free parking?
Absolutely! We offer over 10 house rentals with free parking in Charles Town. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Charles Town?
Experience the best of Charles Town with our house rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

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