Vacation rentals in Shepherdstown, WV

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

Discover Central Vacation Rentals in Shepherdstown, WV

Stay in downtown Shepherdstown, WV to keep top attractions within walking distance. Browse our central vacation rentals and find your perfect base.

Cozy House In Walking Distance To Artistic & Historic Town; Pet-friendly! - Shepherdstown, WV
9.6 4 reviews

Cozy House In Walking Distance To Artistic & Historic Town; Pet-friendly!

apartment, Shepherdstown
This historic house rental in Shepherdstown's historic district offers immediate walking access to shops, restaurants, Shepherd University, and the C&O Canal towpath.
This two-bedroom, two-bathroom residence accommodates up to five guests and features a two-story deck with a fire pit, a patio with a grill, and a soaking tub, with Harpers Ferry and Antietam Battlefield a 10-minute drive away.
Downtown: Explore Shepherdstown From Cozy 1br Apar - Shepherdstown, WV
9.9 453 reviews

Downtown: Explore Shepherdstown From Cozy 1br Apar

apartment, Shepherdstown
This one-bedroom apartment is located in downtown Shepherdstown, within walking distance of the Potomac River and Shepherd University, making it an ideal base for exploring the town's historic charm and natural beauty. The apartment consistently receives excellent ratings for its location, cleanliness, and overall experience.
The rental features a fully equipped kitchen, a comfortable living space, and a private bathroom, comfortably accommodating up to three guests. The apartment offers amenities like fast internet, streaming services, and a reserved parking space, ensuring a convenient and enjoyable stay.
Charming And Cozy, Walk To Town - Shepherdstown, WV
9.7 12 reviews

Charming And Cozy, Walk To Town

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.
Quaint Mini Cottage In Shepherdstown - Walking Distance - Shepherdstown, WV
9.8 23 reviews

Quaint Mini Cottage In Shepherdstown - Walking Distance

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.

Best Shepherdstown, WV vacation rentals with air conditioning

Charming Studio Apt On German St - Shepherdstown, WV
9.8 287 reviews

Charming Studio Apt On German St

apartment, Shepherdstown
This studio apartment is located on German Street in downtown Shepherdstown, just a short walk from Shepherd University, restaurants, and shops. It has received excellent ratings for its location, cleanliness, and overall experience.
The apartment is ideal for a couple, with a queen-sized bed and a fully equipped kitchen featuring granite countertops and handcrafted cabinetry. Amenities include air conditioning, free parking, and a Smart TV, allowing you to relax and enjoy your stay.
Exclusive Wooded Chalet W Magnificent River Views - Shepherdstown, WV
9.9 96 reviews

Exclusive Wooded Chalet W Magnificent River Views

apartment, Shepherdstown
Eagles Bluff Overlook chalet, near Shepherdstown, West Virginia, offers breathtaking Potomac River views, a 15-minute drive from Shepherdstown and the C&O Canal, and under a 30-minute drive from Harpers Ferry.
This four-bedroom, three-bathroom vacation home sleeps eight, boasting two king suites with private baths, a fully equipped kitchen, multiple living areas with smart TVs, a propane fire pit, and a grill for outdoor enjoyment.
Charming Cabin In The Woods With River Access - Shepherdstown, WV
9.6 53 reviews

Charming Cabin In The Woods With River Access

cabin, Shepherdstown
This West Virginia riverfront cottage boasts 720 square feet of space, five miles from Shepherdstown, ten miles from Harpers Ferry, and an hour from Washington, D.C., offering easy access to Antietam Battlefield and other Civil War sites.
The two-bedroom, one-bathroom home sleeps four, features a private 150-foot Potomac River shoreline perfect for kayaking and fishing, a fully equipped kitchenette (excluding a full stove), fast Wi-Fi, and outdoor spaces with a fire pit and gas grill.
Vacation Rental: The Loft At The Barn - Shepherdstown, WV
10 4 reviews

Vacation Rental: The Loft At The Barn

apartment, Bolivar
This apartment in Harpers Ferry is located within walking distance of Vivo Day Spa and Woodpecker Woods Wildlife Sanctuary, and offers easy access to Harpers Ferry National Historical Park, Nash Farm National Park, Hollywood Casino at Charles Town Races, and Ram Stadium.
This 1-bedroom, 1-bathroom unit accommodates up to 4 guests and includes on-site parking, a full kitchen with a refrigerator and microwave, air conditioning, Wi-Fi, and linens.

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.

Popular destinations

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.

Hillside Hideaway In Lowertown Harpers Ferry - Shepherdstown, WV
10 23 reviews

Hillside Hideaway In Lowertown Harpers Ferry

cabin, Harpers Ferry
This Harpers Ferry vacation rental is ideally situated a 3-minute walk from Harpers Ferry Station, a 5-minute walk from the Armory Grounds and Civil War Museum, and a 10-minute walk from the John Brown Wax Museum and Harpers Ferry National Historical Park.
This 1500-square-foot cabin sleeps four guests in two bedrooms and two bathrooms, and features a fully equipped kitchen, a terrace, on-site barbecue grills, and a fireplace; enjoy the living plant wall and excellent user ratings.
Taylors Landing Retreat, 6 Acres, C&o Canal Access, Event-friendly Riverfront - Shepherdstown, WV
8.2 66 reviews

Taylors Landing Retreat, 6 Acres, C&o Canal Access, Event-friendly Riverfront

apartment, Mercersville
This Shepherdstown waterfront home offers easy access to the Chesapeake & Ohio Canal towpath, Antietam National Battlefield (within 3 miles), and the Potomac River (within 3 miles).
This three-bedroom, two-bathroom vacation rental sleeps eight, features a fully equipped kitchen, free WiFi, a private balcony, and pet-friendly accommodations.
Knoxville Home: On-site Hiking & Outdoor Kitchen! - Shepherdstown, WV
9.8 10 reviews

Knoxville Home: On-site Hiking & Outdoor Kitchen!

apartment, Garretts Mill
This Knoxville vacation home offers 4000 square feet of living space on a 17-acre property with private hiking access to the Elk Mountain trail system, located 9 miles from Harpers Ferry National Historical Park and Antietam National Battlefield, and within 18-22 miles of several golf courses.
This pet-friendly rental accommodates up to 8 guests with 3 bedrooms and 2 bathrooms, featuring two kitchens, laptop-friendly workspaces, two washers/dryers, a charcoal grill, and a wood-burning fire pit, providing spectacular sunset views and convenient access to outdoor adventures.
Modern 2-bedroom 2-bed Apartment With Private Access Door Near I-81 - Shepherdstown, WV
9.4 8 reviews

Modern 2-bedroom 2-bed Apartment With Private Access Door Near I-81

apartment, Falling Waters
This Falling Waters apartment rental is conveniently located near Hagerstown Regional Airport (18 miles), Locust Hill Golf Course (28 miles), and the Appalachian Trail Conference Headquarters (30 miles).
This 800-square-foot, two-bedroom, one-bathroom unit sleeps seven and features free Wi-Fi, free parking, a fully equipped kitchen, air conditioning, and a sun terrace.

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.

Promo 5% Weekly And 10% Monthly Discount! Beautiful River In Front Of Home - Shepherdstown, WV
9.6 49 reviews

Promo 5% Weekly And 10% Monthly Discount! Beautiful River In Front Of Home

apartment, Falling Waters
This waterfront home is located in Falling Waters, just a short drive from Williamsport, offering easy access to both the Chesapeake and Ohio Canal National Historic Park and Greenbrier State Park. It has received excellent user ratings, making it a popular choice for travelers. This 5-bedroom, 3-bathroom house provides ample space for families or groups. You'll enjoy the updated kitchen, sunroom, multiple decks, a private boat ramp, and pontoon dock, perfect for enjoying the stunning river views and local attractions.
Shenandoah Paradise  Best River & Mountain Views In Harpers Ferry - Shepherdstown, WV
10 81 reviews

Shenandoah Paradise Best River & Mountain Views In Harpers Ferry

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.
Wingspan Cabin - Shepherdstown, WV
9.8 24 reviews

Wingspan Cabin

cabin, Mount Briar
This Western Maryland A-frame home sits on 14 acres, five minutes from Antietam National Battlefield and under two hours from Washington, D.C., and Baltimore.
The 4-bedroom, 3-bathroom lodge sleeps 10 guests and boasts a game room, private sauna, hot tub, fully fenced backyard with fire pit, and a spacious open-concept kitchen, dining, and living area with a fireplace and Smart TV.
Historic Booth House At The Harpers Ferry Koa - Shepherdstown, WV
9.6 28 reviews

Historic Booth House At The Harpers Ferry Koa

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

Wv Blue And Gold (Entire Property) - Shepherdstown, WV
10 15 reviews

Wv Blue And Gold (Entire Property)

apartment, Shepherdstown
Day Street - Walk To Harpers Ferry Np - Shepherdstown, WV
9.3 9 reviews

Day Street - Walk To Harpers Ferry Np

apartment, Bolivar
Nature Haven Near Harpers Ferry - Shepherdstown, WV
9.8 12 reviews

Nature Haven Near Harpers Ferry

gîte, Garretts Mill
Historic Rockdale Private Barn Loft - Shepherdstown, WV
9.6 35 reviews

Historic Rockdale Private Barn Loft

farm, Ranson

Our Favorite 5-Star Vacation Rentals in Shepherdstown, WV

Discover ultimate relaxation in a luxury Shepherdstown, WV vacation rental, where comfort meets a central, prime location.

Stone House Mansion (1757)- Basement Apartment - Shepherdstown, WV
9.5 30 reviews

Stone House Mansion (1757)- Basement Apartment

apartment, Ranson

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.

The Cute Condo- 2 Bedroom Apartment - Shepherdstown, WV
No reviews

The Cute Condo- 2 Bedroom Apartment

apartment, Martinsburg
Hidden Creekside Retreat Near 5 National Parks, Including Harpers Ferry - Shepherdstown, WV
9.8 10 reviews

Hidden Creekside Retreat Near 5 National Parks, Including Harpers Ferry

apartment, Ranson
Riverkeeper Inn, Waterfront Property On The Potomac River - Shepherdstown, WV
9.4 142 reviews

Riverkeeper Inn, Waterfront Property On The Potomac River

cottage, Harpers Ferry
West Virginia Rental Vacation Home - Shepherdstown, WV
9.9 24 reviews

West Virginia Rental Vacation Home

house, Ranson

Search Vacation Rentals with Swimming Pool in Shepherdstown, WV

Choose a Shepherdstown, WV rental with a pool for a refreshing swim right in the heart of the city.

Harpers Ferry Apartment W/ Private Pool & Hot Tub! - Shepherdstown, WV
9.8 262 reviews

Harpers Ferry Apartment W/ Private Pool & Hot Tub!

apartment, Bolivar
Rest And Relaxation While Enjoying Nature - Shepherdstown, WV
10 1 review

Rest And Relaxation While Enjoying Nature

cabin, Shepherdstown
Antietam Creek - Quiet 2 Bedroom Cabin - Shepherdstown, WV
9.2 96 reviews

Antietam Creek - Quiet 2 Bedroom Cabin

cabin, Keedysville
Quiet Antietam Cabin - Shepherdstown, WV
9.6 128 reviews

Quiet Antietam Cabin

cabin, Keedysville

Explore Vacation Rentals with Jacuzzi in Shepherdstown, WV

Unwind after exploring the city with a private hot tub in your own Shepherdstown, WV vacation rental.

Light Horse Inn: Suite 1 - Shepherdstown, WV
10 2 reviews

Light Horse Inn: Suite 1

apartment, Bolivar
Minutes To Downtown Harpers Ferry - Shepherdstown, WV
9.6 30 reviews

Minutes To Downtown Harpers Ferry

cabin, Bolivar
Serene Retreat By The Potomac - Shepherdstown, WV
No reviews

Serene Retreat By The Potomac

house, Falling Waters
Family Farmside Getaway W/ Hot Tub In Fairplay! - Shepherdstown, WV
No reviews

Family Farmside Getaway W/ Hot Tub In Fairplay!

apartment, Breathedsville
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