Vacation rentals in Shepherdstown, WV

12 available vacation rental offers

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Shepherdstown, WV vacation rentals
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Best Vacation rentals and Airbnb offers in Shepherdstown, WV

Day Street - Walk To Harpers Ferry Np - Shepherdstown, WV
9.2 8 reviews
Shepherdstown, WV
10/23 – 11/01
$124/nighttotal: $1116 (9 )

Day Street - Walk To Harpers Ferry Np

1 1
apartment, Bolivar
This Bolivar, West Virginia apartment is conveniently located near Harpers Ferry National Historical Park (1.6 miles) and the Appalachian Trail Conference Headquarters (3.3 miles), offering easy access to outdoor recreation and historical sites.
This one-bedroom rental features a 60-square-foot floor area, sleeps three guests, includes a fully equipped kitchen, private garden, free Wi-Fi, free parking, and a private entrance.
Charming And Cozy, Walk To Town - Shepherdstown, WV
9.6 10 reviews
Shepherdstown, WV
08/20 – 08/28
$169/nighttotal: $1352 (8 )

Charming And Cozy, Walk To Town

1 2
apartment, Shepherdstown
This Shepherdstown cottage is located within walking distance of the downtown area, offering easy access to shops, restaurants, and historical sites.
The one-bedroom, one-bathroom cottage sleeps four with a queen bed in a loft, a trundle daybed, and a sleeper sofa, featuring a kitchen with a fridge, freezer, and microwave, plus air conditioning, parking, and internet access.
Mountain Farmhouse Suite Near Harpers Ferry - Shepherdstown, WV
9.8 135 reviews
Shepherdstown, WV
08/20 – 08/28
$131/nighttotal: $1048 (8 )

Mountain Farmhouse Suite Near Harpers Ferry

1 2
apartment, Garretts Mill
This one-bedroom apartment is located in Garretts Mill, just a short drive from Harpers Ferry, the C&O Canal, the Appalachian Trail, and the Shenandoah and Potomac Rivers, offering easy access to outdoor adventures. The apartment has consistently received excellent ratings for its cleanliness, location, and overall experience.
The apartment features a king-size bed and a double sofa bed, comfortably accommodating up to four guests. You'll find a fully equipped kitchen with a refrigerator, microwave, coffee maker, dishes, and utensils, along with a dining table for enjoying meals.
6-acre Garden Home Across From Canal Near Antietam - Shepherdstown, WV
9.0 2 reviews
Shepherdstown, WV
09/20 – 09/21
$398/nightfor 1 night

6-acre Garden Home Across From Canal Near Antietam

1 2
apartment, Mercersville
This 3-bedroom, 2-bathroom countryside retreat near Sharpsburg, Maryland, offers a secluded setting directly across from the canal, ideal for exploring canal trails and enjoying river activities, with proximity to historic battlefields.
This pet-friendly apartment accommodates up to 8 guests and features a full kitchen, air conditioning, and internet, set on six acres with mature trees, gardens, and open lawn space for a quiet unwind in a natural environment.
Quaint Mini Cottage In Shepherdstown - Walking Distance - Shepherdstown, WV
9.6 14 reviews
Shepherdstown, WV
10/23 – 11/01
$150/nighttotal: $1350 (9 )

Quaint Mini Cottage In Shepherdstown - Walking Distance

1 1
cottage, Shepherdstown
This Shepherdstown cottage offers a central location, a 7-minute walk from the Shepherdstown Opera House and a 10-minute walk from the tourism information center, placing you near key attractions like the Chesapeake & Ohio Canal National Historic Park.
The one-bedroom, one-bathroom rental sleeps six, features a kitchenette with microwave, oven, and hob, air conditioning, and is within easy reach of the Shepherdstown Museum and Hollywood Casino at Charles Town Races.
Welcome To This Patch Of Serenity On The River's Edge, To This Hideaway. - Shepherdstown, WV
9.8 72 reviews
Shepherdstown, WV
10/23 – 11/01
$1040/nighttotal: $9360 (9 )

Welcome To This Patch Of Serenity On The River's Edge, To This Hideaway.

3 1
apartment, Shepherdstown
This waterfront vacation home is located just 6 miles from the Potomac River, Morgan's Grove Park, and Shepherdstown Museum, offering easy access to local attractions and a peaceful setting. Guests consistently rate this property as excellent, highlighting its comfortable amenities and family-friendly atmosphere. This 3-bedroom, 2-bathroom house spans 2,100 square feet and comfortably accommodates up to 8 guests. Enjoy a fully equipped kitchen, a private garden with a barbecue grill, and a relaxing spa, all while taking in stunning views of the water.
Melvin Hill Farm Est 1765. Readaptive Use Of Barn - Shepherdstown, WV
9.6 9 reviews
Shepherdstown, WV
08/20 – 08/28
$130/nighttotal: $1040 (8 )

Melvin Hill Farm Est 1765. Readaptive Use Of Barn

1 2
farm, Shenandoah Junction
This converted Milking Barn farm stay is located in Shenandoah Junction, West Virginia, situated midway between Harpers Ferry and Shepherdstown, offering convenient access to both historic towns.
The accommodation features one bedroom with a sleeper sofa, a full kitchen, outdoor grilling facilities, a fire pit, and an EV charger, comfortably sleeping up to 4 guests.
Modern Cabin, Kids' Playhouse, Firepit, 5acres, Across River From Harpers Ferry - Shepherdstown, WV
Shepherdstown, WV
09/20 – 09/21
$653/nightfor 1 night

Modern Cabin, Kids' Playhouse, Firepit, 5acres, Across River From Harpers Ferry

3 2
cabin, Dargan
This modern lodge in Dargan offers a secluded setting on nearly 5 wooded acres, providing privacy and frequent deer sightings, with the C&O Canal Towpath and Dargan Boat Ramp just minutes away, and historical sites like Harpers Ferry National Historical Park and Antietam Battlefield within a 20-mile radius. This family-friendly cabin accommodates up to 8 guests with 3 bedrooms and 3 bathrooms, featuring a custom kitchen, radiant heated floors, a firepit, a kid-sized playhouse, a loft workspace, and a foosball/air hockey table, with amenities such as toys, books, a pack-n-play, high chair, stroller, and child carrier hiking backpack.
Riverside Cottage, Minutes From Historic Harpers Ferry!  Private River Access! - Shepherdstown, WV
9.8 156 reviews
Shepherdstown, WV
08/20 – 08/28
$166/nighttotal: $1328 (8 )

Riverside Cottage, Minutes From Historic Harpers Ferry! Private River Access!

2 2
apartment, Harpers Ferry
This charming cottage is located just seven miles from downtown Harpers Ferry, offering a peaceful retreat overlooking the Potomac River. Guests consistently rate this cottage excellent for its amenities and location.
The two-bedroom home comfortably sleeps five guests and features a fully equipped kitchen, two bathrooms, a spacious living area, and a private deck with river views. Enjoy amenities like central air conditioning, Wi-Fi, a private boat launch, and a riverside commons area perfect for relaxing and enjoying the natural beauty of the area.
The Gw Hollida Cottage Of Shepherdstown - Shepherdstown, WV
9.9 336 reviews
Shepherdstown, WV
09/20 – 09/21
$136/nightfor 1 night

The Gw Hollida Cottage Of Shepherdstown

1 2
apartment, Shepherdstown
This Shepherdstown WV cottage sits directly behind the historic G.W. Hollida House, offering a tranquil retreat on five acres.
The one-bedroom, one-bathroom cabin sleeps three guests and features a kitchenette, private porch, sauna, and fire pit; nearby attractions include Shepherdstown's historic district.
Historic Rockdale Private Barn Loft - Shepherdstown, WV
9.6 32 reviews
Shepherdstown, WV
09/01 – 09/08
$96/nighttotal: $672 (7 )

Historic Rockdale Private Barn Loft

1 2
farm, Ranson
This renovated pole barn farm stay near Ranson, West Virginia, offers a secluded retreat on 25 acres, just a 10-minute drive from Shepherdstown and 15 minutes from Charles Town.
The one-bedroom, one-bathroom property sleeps two guests and features a fully equipped kitchenette with modern appliances, a spacious upstairs workstation, high-speed Starlink Wi-Fi, and private parking for two vehicles, plus nature trails and goat encounters on the property.
1799 Inn Harpers Ferry - Shepherdstown, WV
9.1 229 reviews
Shepherdstown, WV
10/23 – 11/01
$185/nighttotal: $1665 (9 )

1799 Inn Harpers Ferry

1 1
apartment, Harpers Ferry
This Harpers Ferry apartment is conveniently located within a 5-minute walk of Harpers Ferry National Historical Park and 4.7 miles from the Appalachian Trail Conference Headquarters, making it ideal for exploring the area's history and natural beauty. The apartment has received excellent ratings for its cleanliness, location, and overall experience.
This one-bedroom rental features a comfortable layout with a private bathroom and a seating area for relaxation. Amenities include air conditioning, a flat-screen TV, a terrace, and a kitchen with a fridge, freezer, microwave oven, and a toaster.

Choose the Right Family-Friendly Vacation Rentals in Shepherdstown, WV

These kid-friendly vacation rentals in Shepherdstown, WV keep you close to top city attractions for a stress-free family vacation.

Antietam Retreat At Blue Haven - Shepherdstown, WV
10 9 reviews
Shepherdstown, WV
08/20 – 08/28
$266/nighttotal: $2128 (8 )

Antietam Retreat At Blue Haven

1 2
cabin, Mount Briar
This Mount Briar cabin rental near Shepherdstown, West Virginia, is conveniently located 10 minutes from Antietam National Battlefield and a short drive from Harper's Ferry and the Chesapeake & Ohio Canal.
The one-bedroom, one-bathroom cottage sleeps five guests and features a kitchen, air conditioning, internet, parking, and a private 12-acre property with a koi pond, offering access to hiking, biking, and whitewater rafting.
Riverkeeper Inn, Waterfront Property On The Potomac River - Shepherdstown, WV
9.2 139 reviews
Shepherdstown, WV
09/01 – 09/08
$224/nighttotal: $1568 (7 )

Riverkeeper Inn, Waterfront Property On The Potomac River

1 2
cottage, Harpers Ferry
This waterfront cabin is located just a short walk from the Potomac River and within a 6-mile radius of both the Chesapeake and Ohio Canal National Historic Park and the Civil War Living History Museum, offering easy access to Harpers Ferry's rich history and outdoor activities. This charming cottage has received excellent user ratings, making it a popular choice for travelers.
The cabin offers 580 square feet of comfortable living space, featuring one bedroom and one bathroom. Guests can enjoy modern amenities like free Wi-Fi, a kitchen with a refrigerator, a washing machine, and a Smart TV with a DVD player, as well as outdoor amenities like a garden and barbecue grills.
Charming River House And Cottage In Shepherdstown - Shepherdstown, WV
Shepherdstown, WV
08/20 – 08/28
$460/nighttotal: $3680 (8 )

Charming River House And Cottage In Shepherdstown

3 2
apartment, Shepherdstown
This waterfront cottage, named The River House and The River Cottage, is located on the Potomac River, just downstream from historic Shepherdstown, offering 100 feet of private waterfront and proximity to the Shepherdstown Museum and Shepherdstown Opera House. This retreat accommodates up to 12 guests across two units with 3 bedrooms and 3 bathrooms, featuring a full kitchen, air conditioning, a garden, a tennis court, parking, expansive river views, a screened porch, a family room with a fireplace, and on-site recreational amenities including kayaks and ping pong.
Historic Booth House At The Harpers Ferry Koa - Shepherdstown, WV
9.6 27 reviews
Shepherdstown, WV
10/23 – 11/01
$570/nighttotal: $5130 (9 )

Historic Booth House At The Harpers Ferry Koa

6 1
apartment, Bolivar
This family-friendly vacation home is located in Harpers Ferry, within walking distance of the Civil War Living History Museum and the Shenandoah River. It has received excellent user ratings.
The house has 6 bedrooms and can accommodate up to 12 guests. It offers amenities like a swimming pool, jacuzzi, terrace, garden, parking, and a fully equipped kitchen.

Best Shepherdstown, WV vacation rentals with parking

Lock Keepers Cottage On C&o Canal/potomac River - Shepherdstown, WV
9.9 232 reviews
Shepherdstown, WV
09/01 – 09/08
$182/nighttotal: $1274 (7 )

Lock Keepers Cottage On C&o Canal/potomac River

3 2
house, Mercersville
Lock Keepers Cottage, a three-bedroom house in Sharpsburg, Maryland, offers a unique canal-side location with scenic views of the C&O Canal and Potomac River, 25 miles from the Appalachian Trail Conference Headquarters and 26 miles from Harpers Ferry National Historical Park.
This 1,120-square-foot family-friendly rental features a fully equipped kitchen, a terrace, a garden, free Wi-Fi, and private parking; nearby recreational activities include skiing and cycling.
Thomas Place - Shepherdstown, WV
9.2 5 reviews
Shepherdstown, WV
10/23 – 11/01
$186/nighttotal: $1674 (9 )

Thomas Place

1 1
apartment, Bolivar
This Bolivar, West Virginia apartment is conveniently located one mile from Harpers Ferry National Historical Park and 3.7 miles from the Appalachian Trail Conference Headquarters.
The one-bedroom unit sleeps seven, features a fully equipped kitchenette with microwave and oven, free Wi-Fi, a private garden, private parking, and a washing machine; guests can enjoy easy access to hiking trails and historical sites.
5-minute Walk To Winery & Battlefield 1-acre Wine Weekend Getaway W/ Fire Pit - Shepherdstown, WV
9.9 276 reviews
Shepherdstown, WV
10/23 – 11/01
$290/nighttotal: $2610 (9 )

5-minute Walk To Winery & Battlefield 1-acre Wine Weekend Getaway W/ Fire Pit

3 1
apartment, Sharpsburg
This apartment is located on a hilltop in the Antietam district of Sharpsburg, just a short walk from Antietam Creek Vineyards and a short drive to the Antietam Battlefield. The apartment has excellent user, location, and cleanliness ratings.
This comfortable 3-bedroom, 1-bathroom rental can accommodate up to 6 guests in its 1040 square feet of space. The apartment features a fully equipped kitchen, a spacious living room, a private garden, and a hot tub with stunning views of the surrounding mountains and battlefield.
5,000 Sq Ft Antebellum Farmhouse 3 Mi To Antietam! - Shepherdstown, WV
10 5 reviews
Shepherdstown, WV
09/01 – 09/08
$348/nighttotal: $2436 (7 )

5,000 Sq Ft Antebellum Farmhouse 3 Mi To Antietam!

4 2
apartment, Bakersville
This non-smoking farm rental in Boonsboro is located a 6-minute drive from the Chesapeake and Ohio Canal and the Potomac River, offering easy access to hiking trails.
This 5010 square foot vacation home accommodates 8 guests with 4 bedrooms, 2 bathrooms, a full kitchen including a dishwasher, air conditioning, internet, and a garden with a terrace.

Frequently Asked Questions about vacation rentals in Shepherdstown, WV

  • What sports or outdoor activites can visitors enjoy in and around Shepherdstown, WV?

    Shepherdstown is a haven for outdoor enthusiasts. You can go kayaking or canoeing on the Potomac River, hiking in Harpers Ferry National Historical Park, or even go rock climbing at the Shenandoah National Park, a short drive away.
  • What are the best Airbnb and vacation rentals in Shepherdstown, WV?

  • What other towns or cities can be easily accessed from Shepherdstown, WV?

    Shepherdstown is conveniently located near several other interesting towns and cities. You can easily visit Harpers Ferry, Winchester, and Charles Town for a day trip. Even Washington, D.C. is a reasonable drive, about an hour and a half away.
  • What are the most popular Airbnbs in Shepherdstown, WV?

  • What amenities are commonly available in vacation rentals in Shepherdstown, WV?

    Vacation rentals in Shepherdstown usually offer basic amenities like Wi-Fi, a kitchen, and laundry facilities. Many also come with outdoor spaces like patios or decks, perfect for enjoying the beautiful scenery.
  • What are the best vacation rentals with a pool in Shepherdstown, WV?

    The best vacation rental with a pool in Shepherdstown, WV is Cottage In Shepherdstown.

  • What time of year is best to rent a vacation rental Shepherdstown, WV?

    The best time to visit Shepherdstown depends on what you're looking for. Spring and fall offer mild weather and vibrant foliage, while summer is great for outdoor activities. If you prefer quieter crowds and lower prices, consider visiting during the shoulder seasons.
  • What are the best rentals for families and kids in Shepherdstown, WV?

  • What are the local dishes in Shepherdstown, WV region?

    Shepherdstown's food scene is a blend of Southern comfort food and Appalachian specialties. You'll find plenty of fried chicken, BBQ, and cornbread. Don't miss the local craft breweries and wineries, offering unique flavors and a taste of the region.
  • What are the best rentals or Airbnbs with a jacuzzi in Shepherdstown, WV?

    The best vacation rentals or Airbnb with a jacuzzi in Shepherdstown, WV are Best Location: Historic Shepherdstown Getaway, Cottage In Shepherdstown and Wine Weekend Getaway-battlefield & Vineyard Views.

Destinations nearby

Guest-Favorite Vacation Rentals with a Terrace in Shepherdstown, WV

Wake up to breathtaking views at these Shepherdstown, WV vacation rentals with balconies, perfect for your morning coffee.

Exclusive Wooded Chalet W Magnificent River Views - Shepherdstown, WV
10 19 reviews
Shepherdstown, WV
09/01 – 09/08
$671/nighttotal: $4697 (7 )

Exclusive Wooded Chalet W Magnificent River Views

4 2
apartment, Shepherdstown
Eagles Bluff Overlook chalet, near Shepherdstown, West Virginia, offers breathtaking Potomac River views, a 15-minute drive from Shepherdstown and under 30 minutes from Harpers Ferry.
This 2,530-square-foot vacation home features four bedrooms, four bathrooms, sleeps eight, and includes a fully equipped kitchen, multiple fireplaces, a private terrace, and a lower-level private entrance.
Shire Cottage: We're Looking For Someone To Share In An Adventure In Wv. - Shepherdstown, WV
Shepherdstown, WV
08/20 – 08/28
$586/nighttotal: $4688 (8 )

Shire Cottage: We're Looking For Someone To Share In An Adventure In Wv.

4 2
apartment, Harpers Ferry
Shire Cottage, a fantasy-themed rental, is located in historic Harpers Ferry, WV, just 5 minutes from downtown attractions and Harpers Ferry National Historical Park.
This 1690 sq ft cottage accommodates up to 8 guests with 4 bedrooms and 2 bathrooms, featuring a hot tub, fire pit, BBQ grill, and entertainment options like smart TVs and board games, with opportunities for wildlife viewing and proximity to wineries, breweries, casinos, and cities like Washington D.C. and Baltimore within an hour's drive.
Shenandoah Paradise  Best River & Mountain Views In Harpers Ferry\n - Shepherdstown, WV
10 77 reviews
Shepherdstown, WV
08/20 – 08/28
$361/nighttotal: $2888 (8 )

Shenandoah Paradise Best River & Mountain Views In Harpers Ferry\n

3 2
apartment, Bolivar
This vacation home is located in the mountains, just a short distance from Vivo Day Spa and Harpers Ferry National Historical Park, making it a perfect base for exploring the area's natural beauty and historical sites. It has received excellent guest ratings, indicating a comfortable and enjoyable stay.
This 2400-square-foot house can accommodate up to 6 guests in its 4 bedrooms and 4 bathrooms. Enjoy a peaceful mountain setting with amenities like a Jacuzzi, a terrace, a garden, and a fireplace, perfect for relaxing and entertaining.
5,000 Sq Ft Antebellum Farmhouse 3 Mi To Antietam! - Shepherdstown, WV
Shepherdstown, WV
08/20 – 08/28
$327/nighttotal: $2616 (8 )

5,000 Sq Ft Antebellum Farmhouse 3 Mi To Antietam!

4 2
house, Bakersville
This historic family farm property is located in Fairplay, 3 miles from Antietam Historic Site, 19 miles from the Appalachian Trail Conference Headquarters, and 21 miles from Harpers Ferry National Historical Park, offering a unique rural experience for visitors to Bakersville.
This 5,010 square foot farmhouse accommodates up to 15 guests with 4 bedrooms, a living room, and a fully equipped kitchen, featuring air conditioning, complimentary WiFi, and an outdoor dining area for a comfortable stay.

Top-Rated Pet-Friendly Vacation Rentals in Shepherdstown, WV

Experience a pet-friendly stay in Shepherdstown, WV with vacation rentals located steps away from city dog parks and walking trails.

Queen Bees Honey Hive - Shepherdstown, WV
10 50 reviews
Shepherdstown, WV
10/23 – 11/01
$294/nighttotal: $2646 (9 )

Queen Bees Honey Hive

3 1
apartment, Shenandoah Junction
This Shenandoah Junction apartment is conveniently located just five minutes from the Hollywood Casino and Racetrack, offering easy access to nearby attractions like Shepherdstown, Charles Town, and Harpers Ferry. The apartment boasts excellent user, location, and cleanliness ratings, making it a popular choice for travelers.
The spacious 3-bedroom, 2-bathroom home comfortably accommodates up to 7 guests. Enjoy a range of amenities including a private pool, a hot tub (coming soon), a fenced-in yard, a propane fireplace, and a dedicated entertainment room with a 55-inch Smart TV and a variety of streaming services.
Rural Home, Hot Tub, Campfire, Hardwood Floors - Shepherdstown, WV
9.6 324 reviews
Shepherdstown, WV
08/20 – 08/28
$228/nighttotal: $1824 (8 )

Rural Home, Hot Tub, Campfire, Hardwood Floors

4 2
apartment, Bolivar
This family-friendly vacation home is located in a peaceful rural setting just two miles from Harpers Ferry's historical sites, including the Civil War Living History Museum, John Brown Museum, and Bolivar Heights Scenic Overlook. It has received excellent ratings from previous guests for its location, cleanliness, and overall experience.
The house offers 1,800 square feet of space and can comfortably accommodate up to 12 guests. Enjoy modern amenities like Wi-Fi, a fully equipped kitchen, a Jacuzzi, a private fenced yard, a tennis court, and a spacious terrace or balcony.
Sharpsburg Retreat--civil War Home Near Antietam Battlefield, C&o Canal Towpath - Shepherdstown, WV
9.7 458 reviews
Shepherdstown, WV
08/20 – 08/28
$145/nighttotal: $1160 (8 )

Sharpsburg Retreat--civil War Home Near Antietam Battlefield, C&o Canal Towpath

2 2
apartment, Sharpsburg
This Sharpsburg vacation rental is located within walking distance of Tolson's Chapel and Antietam National Cemetery, and less than a mile from Antietam National Battlefield and Antietam Creek Vineyards, making it an ideal base for exploring the area's rich history and scenic beauty. The property has consistently received excellent ratings from guests for its location, cleanliness, and overall experience.
The two-bedroom home offers 1190 square feet of comfortable living space, comfortably accommodating up to six guests. Guests can enjoy a fully equipped kitchen, a cozy fireplace, a private garden, and a barbecue grill for outdoor dining, as well as modern amenities like free Wi-Fi and a DVD player.
4 King Suites W/ Hot Tub, Fire Pit, Ping Pong, Arcade, Hi Speed Internet - Shepherdstown, WV
10 24 reviews
Shepherdstown, WV
09/01 – 09/08
$645/nighttotal: $4515 (7 )

4 King Suites W/ Hot Tub, Fire Pit, Ping Pong, Arcade, Hi Speed Internet

4 2
apartment, Garretts Mill
This Knoxville vacation home, located within 3 miles of Kennedy Farmhouse, Antietam Dargan Community Park, and the Chesapeake & Ohio Canal, offers a convenient base for exploring Garretts Mill. This 3000-square-foot property boasts four bedrooms, four bathrooms, sleeps ten guests, and includes a fully equipped kitchen, fitness center, jacuzzi, and outdoor barbecue grills.
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