Shepherdstown holiday rentals

We found 952 holiday rentals — enter your dates for availability
Discover a selection of 10 homes and other holiday rentals in Shepherdstown that are perfect for your trip. Whether you're travelling with your children and pets, with friends or just your children, holiday rentals have the amenities that you expect for your stay, which might include a pool and a washer and dryer. You'll be sure to find a property to rent for everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Shepherdstown

Showing deals for:8 Jan - 15 Jan

Interior
Cozy couch in front of the wood burning fire place.
View from the front door, and steps up to the loft area and en-suite bedroom.
New granite soapstone-like countertops
Exceptional
(13 reviews)

Peaceful Pines, luxury 4-bed, mid-century cabin

Hedgesville

8% off
AU$3,815
for 7 nights, 1 cabin
AU$545 per night
includes taxes & fees
Peaceful Pines, luxury 4-bed, mid-century cabin
Gruner Bungalow
Sunroom
Breakfast Area 1
Main Kitchen
Exceptional
(110 reviews)

Gruner Bungalow at Tranquility Farm & Winery

Purcellville

8% off
AU$18,645
for 7 nights, 1 home
AU$2,664 per night
includes taxes & fees
Gruner Bungalow at Tranquility Farm & Winery
15' tall Holiday tree will be up from Thanksgiving to late January. It really is a sight to see!
The deck features ~900 sq ft from the master bedroom to the kitchen and panoramic views of the vineyard and opposing ridge line. Comfortable seating for the whole group!
Welcome to your cooking retreat - Thermador Column Fridge and Freezer, Gas Stove, Huge Kitchen Sink, Coffee and Hot Coco Station and an Austrian Tile Stove
Pool features a connected hot-tub with waterfall into the pool BUT the best feature is the view
Exceptional
(60 reviews)

Vinewood Estate Luxury Pool and Vineyard Retreat

Purcellville

8% off
AU$11,322
for 7 nights, 1 chalet
AU$1,617 per night
includes taxes & fees
Vinewood Estate Luxury Pool and Vineyard Retreat
Interior
Interior
Private kitchen
Property grounds
Exceptional
(13 reviews)

Mountain Retreat • Ski • Tub • Trails • Golf • Arcade • Firepit

Mercersburg

8% off
AU$6,219
for 7 nights, 1 room
AU$888 per night
includes taxes & fees
Mountain Retreat • Ski • Tub • Trails • Golf • Arcade • Firepit
Living area
Exterior
Living area
Private kitchen
Exceptional
(13 reviews)

🍁#1 WV Hospitality🌻5 Master EnSuites🍁TreeTop Fall Foliage🌻Close to Town🍁Hot Tub🌟

Berkeley Springs

8% off
AU$6,896
for 7 nights, 1 cabin
AU$985 per night
includes taxes & fees
🍁#1 WV Hospitality🌻5 Master EnSuites🍁TreeTop Fall Foliage🌻Close to Town🍁Hot Tub🌟
Living area
Interior
Living area
Exterior
Exceptional
(74 reviews)

Family Cabin on 20 Private Acres • Game Room • Near Berkeley Springs

Hancock

15% off
AU$2,521
for 7 nights, 1 cabin
AU$360 per night
includes taxes & fees
Family Cabin on 20 Private Acres • Game Room • Near Berkeley Springs
Wrap around windows and views of nature.
Kitchen has breakfast bars on both ends.
Screened wrap-around porch is built for relaxing, with six Adirondack chairs.
Situated in the middle of the 120 acres, views are on all sides.
Exceptional
(81 reviews)

Luxurious country home. 120 acres. 5 Bedrooms. Basement game room. Fitness Rm.

Berkeley Springs

8% off
AU$4,606
for 7 nights, 1 home
AU$658 per night
includes taxes & fees
Luxurious country home. 120 acres. 5 Bedrooms. Basement game room. Fitness Rm.
Gather and enjoy meals in the spacious, fully stocked kitchen.
Warm up around the fire pit and enjoy the stunning mountain and pastoral views!
Stream your favorite TV shows and movies with high-speed internet.
The Kitchen Nook offers additional seating, and a cozy place to read.
Exceptional
(7 reviews)

The Spring House: Entire Home Rental on 74-acre, Scarlet Springs Farm

Waterford

8% off
AU$5,273
for 7 nights, 1 room
AU$753 per night
includes taxes & fees
The Spring House: Entire Home Rental on 74-acre, Scarlet Springs Farm
View from Hot Tub
Outside View at Twilight
Firepit Area
View from Deck
Exceptional
(291 reviews)

Large Luxury Chalet - Hot Tub, Sauna & VIEWS

Berkeley Springs

7% off
AU$6,280
for 7 nights, 1 home
AU$897 per night
includes taxes & fees
Large Luxury Chalet - Hot Tub, Sauna & VIEWS
Propane logs in each fireplace make a warm fire only a click of a button away!
Sip your morning coffee enjoying these treetop views
Counter-stools offer a front row seat to watch the chef in your group.
WELCOME!We are excited to host your getaway!
Exceptional
(54 reviews)

🎃 Halloween🍁 PEAK Fall Foliage Wkend Open🎃Grab this Hidden Gem TODAY🍁

Berkeley Springs

8% off
AU$5,893
for 7 nights, 1 cabin
AU$842 per night
includes taxes & fees
🎃 Halloween🍁 PEAK Fall Foliage Wkend Open🎃Grab this Hidden Gem TODAY🍁
Dining
Creek right below the property to explore!
Welcome to our Cabin in the Woods!
Screened porch
Exceptional
(240 reviews)

Beautiful Cottage At 'the Woods' Resort, Golf, Spa, Swimming & Resort Amenities

Hedgesville

7% off
AU$2,315
for 7 nights, 1 cabin
AU$331 per night
includes taxes & fees
Beautiful Cottage At 'the Woods' Resort, Golf, Spa, Swimming & Resort Amenities
View from front porch
Kitchen
Sunroom
Bedroom 1
Exceptional
(49 reviews)

Firefly Hill - Renovated farmhouse with large backyard - sleeps 8

Jefferson

11% off
AU$2,329
for 7 nights, 1 room
AU$333 per night
includes taxes & fees
Firefly Hill - Renovated farmhouse with large backyard - sleeps 8
Exterior
Terrace/patio
Kitchen Island
Side house stone steps and landscaping
Exceptional
(88 reviews)

Luxurious Mountaintop Chalet / Cabin in 'The Woods Golf Resort':Access Amenities

Hedgesville

8% off
AU$5,599
for 7 nights, 1 cabin
AU$800 per night
includes taxes & fees
Luxurious Mountaintop Chalet / Cabin in 'The Woods Golf Resort':Access Amenities
Terrace/patio
Property grounds
Exterior
Terrace/patio
Exceptional
(331 reviews)

Fox Hollow | Romantic Wooded Retreat w/ Fire Pit & Hot Tub

Berkeley Springs

12% off
AU$3,555
for 7 nights, 1 cabin
AU$508 per night
includes taxes & fees
Fox Hollow | Romantic Wooded Retreat w/ Fire Pit & Hot Tub
Interior
Gather for magical nights under the stars with our newly built deck and patio
Dining
The foyer & welcome room invites you in and provides information on the house and local sights.
Exceptional
(23 reviews)

Walk to Top-Rated Restaurants & Trails! 7BR w/HotTub Gazebo & Built-in FirePit!

Purcellville

8% off
AU$16,119
for 7 nights, 1 home
AU$2,303 per night
includes taxes & fees
Walk to Top-Rated Restaurants & Trails! 7BR w/HotTub Gazebo & Built-in FirePit!
Spacious and luxurious kitchen has double ovens.
Terrace/patio
Well appointed kitchen is central to the downstairs.
Views around the property are superb.
Exceptional
(33 reviews)

Rent the Estate! Sleep up to 20 with no bunk beds. 120 acres and two houses.

Berkeley Springs

8% off
AU$11,436
for 7 nights, 1 home
AU$1,634 per night
includes taxes & fees
Rent the Estate! Sleep up to 20 with no bunk beds. 120 acres and two houses.
Private kitchen
Interior
Exterior
Interior
Exceptional
(22 reviews)

The Lodge at Stoneleigh

Round Hill

20% off
AU$8,986
for 7 nights, 1 home
AU$1,284 per night
includes taxes & fees
The Lodge at Stoneleigh
Room
Terrace/patio
Interior
Living area
Exceptional
(83 reviews)

🍁BE Surrounded by Nature🌲RELAX it’s a 5 Star Luxury Cabin🍁Hot Tub🌲Close to town🍁

Berkeley Springs

8% off
AU$4,749
for 7 nights, 1 cabin
AU$678 per night
includes taxes & fees
🍁BE Surrounded by Nature🌲RELAX it’s a 5 Star Luxury Cabin🍁Hot Tub🌲Close to town🍁
Separate entrance to the apartment, for those who booked for 16+ guests.
Downstairs Bar area with full kitchen
Gas Fireplace in Downstairs Seating Area
Harpers Ferry Vacation Rental - Front View
Exceptional
(116 reviews)

Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

Harpers Ferry

6% off
AU$4,234
for 7 nights, 1 home
AU$605 per night
includes taxes & fees
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
Dining
Fire pit
Private kitchen
Living area
Exceptional
(9 reviews)

Escape from the City. House near Harpers Ferry

Knoxville

8% off
AU$2,269
for 7 nights, 1 cottage
AU$324 per night
includes taxes & fees
Escape from the City. House near Harpers Ferry
Private kitchen
Interior
Dining
Terrace/patio
Exceptional
(27 reviews)

The Cowbell - 3-bedroom farmhouse in charming Berkeley Springs

Berkeley Springs

12% off
AU$2,341
for 7 nights, 1 home
AU$334 per night
includes taxes & fees
The Cowbell - 3-bedroom farmhouse in charming Berkeley Springs
The River is typically this low in July - August. Depending on how much rain
Property grounds
Room
Interior
Exceptional
(88 reviews)

Waterfront Cabin overlooking the Potomac River W/ Hot Tub, firepit, pavilion

Hedgesville

8% off
AU$2,311
for 7 nights, 1 cabin
AU$330 per night
includes taxes & fees
Waterfront Cabin overlooking the Potomac River W/ Hot Tub, firepit, pavilion
Outdoor spa tub
Living area
Living area
Private kitchen
Exceptional
(34 reviews)

Secluded cozy cabin with modern amenities/hot tub/pet friendly/wifi

Berkeley Springs

8% off
AU$2,697
for 7 nights, 1 cabin
AU$385 per night
includes taxes & fees
Secluded cozy cabin with modern amenities/hot tub/pet friendly/wifi
Living Room 2: second gathering space with sofa, 65 inch TV, washer & dryer.
Living room: open-concept gathering space with decorative wood-burning stove.
Exterior: front of The Spy House with covered porch seating.
East Bedroom, 2nd Floor: queen bed, rocking chair, writing desk. Shares hall bathroom.
Exceptional
(175 reviews)

The Spy House, Historic 1880s Home, Harpers Ferry

Harpers Ferry

8% off
AU$2,595
for 7 nights, 1 home
AU$371 per night
includes taxes & fees
The Spy House, Historic 1880s Home, Harpers Ferry

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Head to the historical city of Shepherdstown

The area's history and opera are just some of the reasons to come on holiday to Shepherdstown. Travellers to this scenic city praise the university setting, riverfront and hiking. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in Shepherdstown

Are you searching for top things to see and do while you're in the area? Venture out of your cosy holiday rental and experience everything that makes Shepherdstown a one-of-a-kind holiday spot. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Big Cork Vineyards (7.6 mi / 12.2 km)
  • Locust Hill Golf Course (11.1 mi / 17.8 km)
  • 868 Estate Vineyards (14.2 mi / 22.8 km)
  • Breaux Vineyards (14.4 mi / 23.1 km)
  • Hagerstown Speedway (15.9 mi / 25.5 km)
  • Summit Point Motorsports Park (15.9 mi / 25.7 km)

Exploring the natural landscape of Shepherdstown

Whether you're an outdoor enthusiast or just want to appreciate the scenery, Shepherdstown is a great place to spend some time outside. These are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Crystal Grottoes Caverns (8.2 mi / 13.3 km)
  • Greenbrier State Park (12.2 mi / 19.6 km)
  • Shenandoah Lake Beach (15.2 mi / 24.5 km)
  • James Hite Park (7.5 mi / 12 km)
  • Virginius Island (8.3 mi / 13.3 km)
  • Blue Ridge Center for Environmental Stewardship (10.4 mi / 16.8 km)

Travelling to and around Shepherdstown

Fly into Martinsburg, WV (MRB-Eastern West Virginia Regional), the closest airport, located 10.1 mi (16.3 km) from the city centre. If you can't find a flight that works for your travel itinerary, you might consider flying into Hagerstown, MD (HGR-Hagerstown Regional), which is 19.4 mi (31.2 km) away.

Frequently asked questions

What is the most popular type of holiday rental accomodation in Shepherdstown?
In Shepherdstown, holiday houses are the most common type of holiday rental, with about 14 available throughout the town. These properties typically offer spacious living areas, fully equipped kitchens, and outdoor spaces, making them ideal for families or groups looking for a comfortable stay. Additionally, several cottages, cabins, apartments, and mobile homes are also on offer, providing a range of options for different preferences and budgets.
Are there any family house rentals in Shepherdstown?
In Shepherdstown, West Virginia, there are ten family-friendly house rentals available, making it an excellent choice for those travelling with children. The charming town is known for its beautiful historic architecture and proximity to the Potomac River, providing plenty of outdoor activities and cultural experiences. Many of these homes feature spacious living areas, fully equipped kitchens to prepare family meals, and outdoor spaces where children can play safely.Visitors can enjoy amenities such as Wi-Fi, air conditioning, and laundry facilities, ensuring a comfortable and convenient stay. The local area offers attractions like the Shepherdstown Museum and the nearby C&O Canal National Historical Park, which is great for hiking and exploring nature.
Are there pet-friendly house rentals in Shepherdstown?
In Shepherdstown, there are several pet-friendly house rentals available, making it an excellent choice for those travelling with furry companions. Visitors can expect a range of amenities, including spacious living areas, fully equipped kitchens, and outdoor spaces such as patios or gardens where pets can enjoy the fresh air. Many properties are situated near the picturesque Potomac River, offering scenic views and opportunities for leisurely walks.The historic downtown area of Shepherdstown provides a charming backdrop, with shops and cafes that may also welcome pets. Additionally, the nearby C&O Canal National Historical Park features trails that are great for hiking with dogs, allowing for exploration of the beautiful natural surroundings.
Are there any remote work holiday rentals in Shepherdstown?
In Shepherdstown, West Virginia, there are approximately 20 remote work holiday rentals available, making it a solid choice for those looking to blend work and leisure. Many of these properties are equipped with essential amenities conducive to remote working, including high-speed Wi-Fi, dedicated workspaces, and comfortable desks.Guests can expect a variety of accommodations, from charming historic homes to modern apartments, often featuring spacious living areas and fully equipped kitchens for convenient meal preparation. The picturesque town itself, located along the Potomac River, offers a vibrant setting with local shops, cafes, and scenic parks, great for unwinding after a productive day. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Shepherdstown?
In Shepherdstown, popular holiday rental amenities include fully equipped kitchens, which allow guests to prepare their own meals. Many rentals also feature outdoor spaces like decks or patios, providing a lovely setting for relaxation or dining al fresco. Onsite parking is commonly available, making it convenient for those travelling by car. Additionally, some properties offer porches or lanais, superb for enjoying the picturesque surroundings. Guests can also expect coffee and tea makers, ensuring they can enjoy a warm beverage whenever they wish.
When is the best time to visit Shepherdstown for a holiday rental?
The peak season for visiting Shepherdstown is during the summer months, specifically from June to August. This vibrant period draws in travellers keen to enjoy the warm weather and partake in outdoor activities, as well as explore the town's rich history and cultural events. July, in particular, is a popular month, offering a lively option filled with festivals and community gatherings.During these summer months, temperatures typically range from 20 to 30 degrees Celsius, providing a comfortable climate for outdoor adventures like hiking along the Potomac River or wandering through the scenic streets of this charming town. The lush greenery and historic architecture create a picturesque setting that's great for sightseeing.For those looking for a more budget-friendly option, consider visiting in December. While this month is part of the low season, it offers a magical winter charm, complete with festive decorations and local holiday events. You can experience the warmth of community gatherings and perhaps enjoy a quieter pace, making it a delightful time for a getaway.Ultimately, the best time to visit Shepherdstown for a holiday rental depends on your preferences—whether you wish to immerse yourself in the bustling summer festivities or enjoy a peaceful winter retreat.
What are the top attractions in Shepherdstown?
In Shepherdstown, visitors can explore a variety of attractions that highlight the town's rich history and natural beauty. The historic downtown area is charming, featuring well-preserved 18th-century buildings, local shops, and eateries that capture the small-town atmosphere. The Shepherd University campus adds a vibrant feel to the town, with its lovely green spaces and cultural events.Outdoor enthusiasts can enjoy the nearby C&O Canal National Historical Park, which offers scenic trails for walking and biking along the Potomac River, as well as opportunities for kayaking and fishing. The picturesque Shepherdstown Battlefield is a significant historical site, providing insight into the Civil War's impact on the area.Additionally, the town hosts various festivals throughout the year, such as the Shepherdstown Music and Dance Festival, attracting both locals and visitors.
Are all fees included in the Shepherdstown holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Shepherdstown holiday homes with parking?
Stayz offers a wide selection of holiday homes in Shepherdstown with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Shepherdstown holiday homes?
You can find great discounts on holiday homes in Shepherdstown on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Shepherdstown holiday home booking on Stayz?
To find Shepherdstown holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Shepherdstown?
A long-stay holiday home in Shepherdstown is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Shepherdstown holiday home?
Book your Shepherdstown holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Shepherdstown?
Prices for holiday homes in Shepherdstown vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Shepherdstown to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.