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.

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.
Downtown Modern 2br Step From Dining And Shopping - Shepherdstown, WV
9.9 195 reviews

Downtown Modern 2br Step From Dining And Shopping

apartment, Shepherdstown
This modern two-bedroom apartment is located in downtown Shepherdstown, just a short walk from shops, restaurants, and the Shepherd University campus. The apartment has received excellent ratings for location, cleanliness, and user experience.
The apartment features a versatile work/play room, perfect for those who need to stay connected while on vacation. The kitchen is fully stocked with everything you need to prepare meals, and the apartment also provides high-speed internet and access to streaming services.
Shepherd's Rest - Shepherdstown, WV
9.8 11 reviews

Shepherd's Rest

apartment, Shepherdstown
This 2-bedroom, 2-bathroom rental unit is located in Shepherdstown, West Virginia's oldest town, offering scenic Potomac River views and a 1.5-hour drive to Washington D.C. and Baltimore.
This pet-friendly apartment accommodates up to 5 guests and features a full kitchen with a fridge and dishwasher, air conditioning, and access to a garden, with proximity to Shepherdstown's dining and arts scene.
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.

Best Shepherdstown, WV vacation rentals with air conditioning

The Charming Crib 2 Bedroom Apartment - Shepherdstown, WV
No reviews

The Charming Crib 2 Bedroom Apartment

apartment, Martinsburg
This Martinsburg, West Virginia apartment rental is conveniently located in Berkeley County's lower Shenandoah Valley, near breweries, wineries, hiking trails, the Belle Boyd House, and Apollo Civic Theatre.
This 2260-square-foot, two-bedroom, one-bathroom unit sleeps four and offers free high-speed Wi-Fi, an HD-TV with streaming services, on-site coin laundry, and room service via Brix27; nearby attractions include Whitetail Ski Resort and four golf courses within a 20-minute drive.
6-acre Garden Home Across From Canal Near Antietam - Shepherdstown, WV
No reviews

6-acre Garden Home Across From Canal Near Antietam

chalet, Mercersville
This chalet in Sharpsburg offers a serene retreat across from a canal, conveniently situated 19 miles from the Appalachian Trail Conference Headquarters and 20 miles from Harpers Ferry National Historical Park.
This 1800 square foot accommodation accommodates up to 19 guests with one bedroom and two bathrooms, featuring air conditioning, a fully equipped kitchen, WiFi, and a terrace overlooking a 6-acre garden.
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
This waterfront vacation home near Ranson, West Virginia, is 2.3 miles from A-T Gift Company Farm Winery and within 9 miles of James Hite Park and Hillside Lake.
This 1800-square-foot house features two bedrooms, one bathroom, sleeps eight, and includes a fully equipped kitchen, free Wi-Fi, a patio, and on-request housekeeping, plus a spa, garden, and barbecue grills.
Wv Blue And Gold (Entire Property) - Shepherdstown, WV
10 15 reviews

Wv Blue And Gold (Entire Property)

apartment, Shepherdstown
This four-bedroom, two-bathroom house rental in McShanes Landing, Shepherdstown, offers convenient access to the Potomac River via a cleared path.
The 4-bedroom home sleeps 12, features two retro GE kitchens, a hot tub, grill, four kayaks, strong WiFi with WiFi calling, and on-site assistance from the owners next door.

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.

High Street Retreat - Shepherdstown, WV
10 2 reviews

High Street Retreat

house, Harpers Ferry
High Street Retreat, a house in Harpers Ferry, is located in the heart of town, just a 5-minute walk from Harpers Ferry National Historical Park and 4.5 miles from the Appalachian Trail Conference Headquarters.
This 1420 sq ft retreat accommodates up to 9 guests with 2 bedrooms and 2 bathrooms, offering free WiFi, a fully equipped kitchen, air conditioning, and a private balcony, with complimentary private parking available.
Laurel Cottage In The Heart Of Harpers Ferry - Shepherdstown, WV
10 13 reviews

Laurel Cottage In The Heart Of Harpers Ferry

cottage, Harpers Ferry
This Harpers Ferry vacation home is located in the Upper Town historic district, one block from restaurants and a ten-minute walk from the 19th-Century Village in Lower Town.
This three-bedroom, three-bathroom house boasts 1,700 square feet of space, including an open-plan main floor, a reading loft, and a private garden with a wood-burning fireplace; it comfortably sleeps six guests and is near hiking trails and River and Snow Riders.
Retreat To Antietam/sharpsburg - Shepherdstown, WV
9.7 469 reviews

Retreat To Antietam/sharpsburg

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.
Thomas Place - Shepherdstown, WV
9.2 5 reviews

Thomas Place

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.

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.

Hot Tub, Historic, Rural Setting, Convenient - Shepherdstown, WV
9.5 381 reviews

Hot Tub, Historic, Rural Setting, Convenient

apartment, Bolivar
The Battlefields Inn is a beautifully restored historical home located just outside Bolivar, within walking distance of the National Park Battlefields, offering a peaceful rural setting. The inn has consistently received excellent ratings for its location, cleanliness, and overall user experience.
The spacious home offers 3 bedrooms and 2 bathrooms, accommodating up to 10 guests comfortably. It features a fully equipped kitchen, a Jacuzzi, a terrace, a garden, and a Tesla charger nearby, providing a comfortable and enjoyable stay for families or groups.
Enchanting Cottage, Walk To Downtown Harpers Ferry - Shepherdstown, WV
9.4 72 reviews

Enchanting Cottage, Walk To Downtown Harpers Ferry

house, Harpers Ferry
This charming cottage is located in the heart of historic downtown Harpers Ferry, just a short walk from Harpers Ferry National Historical Park and a short drive from the Appalachian Trail Conference Headquarters and Locust Hill Golf Course. Guests consistently rate this house excellent for its location, cleanliness, and overall experience.
The house offers 1,100 square feet of space and comfortably sleeps 7 guests. Amenities include air conditioning, a fully equipped kitchen, free Wi-Fi, a private patio, and a modern bathroom, making it perfect for families or groups looking for a comfortable and convenient stay.
Bufflehead Lodge - Shepherdstown, WV
10 4 reviews

Bufflehead Lodge

apartment, Dargan
This Keedysville, Maryland apartment offers a secluded escape on 4 acres of wooded property, providing convenient access to historical sites such as Antietam National Battlefield and Harpers Ferry National Historical Park, located approximately 1.5 hours from Washington D.C.
This family-friendly dwelling accommodates up to 6 guests with 2 bedrooms and 2 bathrooms, featuring air conditioning, internet, and a full kitchen with a fridge, freezer, microwave, and dishwasher, ideal for outdoor adventures and historical exploration.
Riverside Cottage, Minutes From Historic Harpers Ferry!  Private River Access! - Shepherdstown, WV
9.8 161 reviews

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

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.

Best Shepherdstown, WV vacation rentals with parking

Riverfront Home In Harpers Ferry - Shepherdstown, WV
9.9 81 reviews

Riverfront Home In Harpers Ferry

apartment, Dargan
Charming Cabin In The Woods With River Access - Shepherdstown, WV
9.6 53 reviews

Charming Cabin In The Woods With River Access

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

Nature Haven Near Harpers Ferry

gîte, Garretts Mill
1900 Newton School-house - Shepherdstown, WV
10 45 reviews

1900 Newton School-house

apartment, Falling Waters

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.

Vacation Rental: The Loft At The Barn - Shepherdstown, WV
10 4 reviews

Vacation Rental: The Loft At The Barn

apartment, Bolivar

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 Creekside Cottage: Downtown | Pet-friendly - Shepherdstown, WV
10 194 reviews

The Creekside Cottage: Downtown | Pet-friendly

apartment, Shepherdstown
Elevated Potomac River Retreat - Shepherdstown, WV
9.9 46 reviews

Elevated Potomac River Retreat

apartment, Antietam
Schilling House - Shepherdstown, WV
9.1 153 reviews

Schilling House

house, Bolivar
Newly Renovated - Walk To Harpers Ferry Np - Shepherdstown, WV
10 4 reviews

Newly Renovated - Walk To Harpers Ferry Np

apartment, Bolivar

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.

Antietam Creek - Quiet 2 Bedroom Cabin - Shepherdstown, WV
9.2 95 reviews

Antietam Creek - Quiet 2 Bedroom Cabin

cabin, Keedysville
Sweeter Than Honey, Comfortable  Beyond The Ordinary Hotel Experience! - Shepherdstown, WV
9.8 13 reviews

Sweeter Than Honey, Comfortable Beyond The Ordinary Hotel Experience!

apartment, Shenandoah Junction
Historic Booth House At The Harpers Ferry Koa - Shepherdstown, WV
9.6 28 reviews

Historic Booth House At The Harpers Ferry Koa

apartment, Bolivar
5 Mi To Harpers Ferry Nhp: Quiet Deck & Garden - Shepherdstown, WV
No reviews

5 Mi To Harpers Ferry Nhp: Quiet Deck & Garden

apartment, Bolivar

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.

Private Home, Hot Tub, Wifi, Rural Setting, Gas Stove, 70" Smarttv - Shepherdstown, WV
9.6 20 reviews

Private Home, Hot Tub, Wifi, Rural Setting, Gas Stove, 70" Smarttv

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
Modern Retreat - 4 King Suites, Saltwater Hot Tub & Game Room  Harpers Ferry - Shepherdstown, WV
10 25 reviews

Modern Retreat - 4 King Suites, Saltwater Hot Tub & Game Room Harpers Ferry

apartment, Garretts Mill
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