Shepherdstown Vacation Rentals

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Check prices for these dates

In two weeks
Apr 24 - Apr 26
In two months
Jun 5 - Jun 7
In three months
Jul 3 - Jul 5
In four months
Jul 31 - Aug 2

Our top choices for Shepherdstown vacation rentals

Exterior

❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.8 out of 10, Exceptional, (72 reviews)
"Cozy home, great location, and kind and helpful host. Would like to stay again. "
United States
Matthew S.
The price is ￥11,496
￥22,520 total
includes taxes & fees
May 4 - May 5
❤️ Secluded 1940s Romantic Tiny House on the River
Dining

Exclusive Wooded Chalet w Magnificent River Views

Exclusive Wooded Chalet w Magnificent River Views
Shepherdstown
10.0 out of 10, Exceptional, (17 reviews)
"The entire stay was wonderful. Fantastic views. "
United States
Downer F.
The price is ￥40,709
￥75,099 total
includes taxes & fees
Apr 9 - Apr 10
Exclusive Wooded Chalet w Magnificent River Views
Interior

Antietam Creek - Quiet 2 Bedroom Cabin

Antietam Creek - Quiet 2 Bedroom Cabin
Keedysville
9.2 out of 10, Wonderful, (89 reviews)
"This was an amazing cabin with a full kitchen so you could cook and enjoy the quiet."
United States
Lina A.
The price is ￥31,934
￥52,468 total
includes taxes & fees
Apr 7 - Apr 8
Antietam Creek - Quiet 2 Bedroom Cabin
Interior

Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Middletown
9.6 out of 10, Exceptional, (112 reviews)
"Cozy & dog friendly "
United States
Lauren F.
The price is ￥13,572
￥32,158 total
includes taxes & fees
Apr 13 - Apr 14
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Dining

~Family & Pet Friendly Mountain Retreat~ Steam Shower~ 5 minutes from lake!

~Family & Pet Friendly Mountain Retreat~ Steam Shower~ 5 minutes from lake!
Harpers Ferry
10.0 out of 10, Exceptional, (85 reviews)
"The host had great communication and the place was exactly as pictured! "
United States
Colleen J.
The price is ￥21,555
￥50,331 total
includes taxes & fees
Apr 13 - Apr 14
~Family & Pet Friendly Mountain Retreat~ Steam Shower~ 5 minutes from lake!
Fridge, microwave, oven, stovetop

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Frederick
10.0 out of 10, Exceptional, (66 reviews)
"Great kitchen, very comfortable beds. Well air conditioned."
United States
Whitney C.
The price is ￥18,538
￥41,315 total
includes taxes & fees
Apr 7 - Apr 8
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Exterior

Charming "Cream of the Crop" Cape ~❤️of Middletown

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (143 reviews)
"Love the place will book again"
United States
WAYNE M.
The price is ￥13,572
￥36,389 total
includes taxes & fees
Apr 9 - Apr 10
Charming "Cream of the Crop" Cape ~❤️of Middletown

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Downtown Frederick
9.4 out of 10, Exceptional, (124 reviews)
"The home was a great location to explore downtown Frederick. It had everything that we needed "
United States
David J.
The price is ￥17,723
￥44,174 total
includes taxes & fees
Apr 7 - Apr 8
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Exterior

Historic cozy farmhouse in the ❤️ of Myersville , MD close to Rt 70! Welcome Home

Historic cozy farmhouse in the ❤️ of Myersville , MD close to Rt 70! Welcome Home
Myersville
9.4 out of 10, Exceptional, (111 reviews)
"Great, unique house full of cool antiques! Host was helpful and communicative, highly recommended for a Myersville stay."
United States
Ryan W.
The price is ￥25,388
￥47,221 total
includes taxes & fees
Apr 8 - Apr 9
Historic cozy farmhouse in the ❤️ of Myersville , MD close to Rt 70! Welcome Home
Dining

Cozy w Fireplace, Fire Pit, Wifi & Pool Access

Cozy w Fireplace, Fire Pit, Wifi & Pool Access
The Woods
9.8 out of 10, Exceptional, (59 reviews)
"The host was very responsive whenever I texted about questions and doing a check in the day of and a check in the day of checkout. The house was beautiful and well maintained and any minor issues I had were quickly addressed. I would definitely stay at this house in the future. "
United States
Paula M.
The price is ￥26,582
￥63,638 total
includes taxes & fees
Apr 7 - Apr 8
Cozy w Fireplace, Fire Pit, Wifi & Pool Access
Interior

Bring Your Own Boat - Meticulously restored house on the Potomac River

Bring Your Own Boat - Meticulously restored house on the Potomac River
Hedgesville
10.0 out of 10, Exceptional, (9 reviews)
"Our stay was amazing and we really enjoyed ourselves. The place was perfect and quiet and peaceful! We will be booking with them again! "
United States
Kyndal B.
The price is ￥11,975
￥25,739 total
includes taxes & fees
Apr 9 - Apr 10
Bring Your Own Boat - Meticulously restored house on the Potomac River
Fridge, microwave, oven, stovetop

Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
Jefferson
9.8 out of 10, Exceptional, (61 reviews)
"The beds were incredibly comfortable. Great house. Great location. "
United States
Julie B.
The price is ￥21,555
￥46,713 total
includes taxes & fees
Apr 12 - Apr 13
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
Interior

The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!

The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Hamilton
9.8 out of 10, Exceptional, (16 reviews)
"Absolutely amazing place and stay! I could not possibly be more impressed and I look forward to coming back."
United States
Jasmine M.
The price is ￥35,926
￥62,618 total
includes taxes & fees
Apr 7 - Apr 8
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Dining

*Luxury Condo In Downtown Frederick*

*Luxury Condo In Downtown Frederick*
Downtown Frederick
9.0 out of 10, Wonderful, (81 reviews)
"The place was perfect. Location is ideal to walk everywhere."
United States
Anonymous traveler
The price is ￥11,784
￥35,340 total
includes taxes & fees
Apr 7 - Apr 8
*Luxury Condo In Downtown Frederick*
Property grounds

Birch Cabin at Hunting Creek Hideaway

Birch Cabin at Hunting Creek Hideaway
Thurmont
10.0 out of 10, Exceptional, (25 reviews)
"Beautiful location. Just what we were looking for."
United States
tony l.
The price is ￥15,089
￥23,611 total
includes taxes & fees
Apr 13 - Apr 14
Birch Cabin at Hunting Creek Hideaway
Interior

2-Bedroom cabin Hot tub Fireplace PS5

2-Bedroom cabin Hot tub Fireplace PS5
2.0 star property
The Woods
8.6 out of 10, Excellent, (4 reviews)
"Nice cabin. Could’ve been cleaner outside. Host was nice and surrounding area, beautiful. "
United States
Chris
The price is ￥25,758
￥44,867 total
includes taxes & fees
Apr 7 - Apr 8
2-Bedroom cabin Hot tub Fireplace PS5
Interior

Antietam Look Out - Incredible Sunset Views!

Antietam Look Out - Incredible Sunset Views!
Keedysville
9.8 out of 10, Exceptional, (36 reviews)
"Great communication, very clean, beautiful views!"
United States
Lorie K.
The price is ￥15,967
￥55,329 total
includes taxes & fees
Apr 20 - Apr 21
Antietam Look Out - Incredible Sunset Views!
Outdoor spa tub

Cottage w/ Hot Tub and 100-Mile Valley Views!

Cottage w/ Hot Tub and 100-Mile Valley Views!
Harpers Ferry
9.8 out of 10, Exceptional, (20 reviews)
"Great view, very secluded"
United States
Matt s.
The price is ￥16,286
￥60,139 total
includes taxes & fees
Apr 23 - Apr 24
Cottage w/ Hot Tub and 100-Mile Valley Views!
Terrace/patio

Spacious w/Hot Tub, Fire Pit, Deck, Grill and WiFi

Spacious w/Hot Tub, Fire Pit, Deck, Grill and WiFi
Sleepy Hollow
8.8 out of 10, Excellent, (29 reviews)
"This is a great property for a quiet and relaxing stay. "
United States
David G.
The price is ￥23,721
￥54,090 total
includes taxes & fees
Apr 7 - Apr 8
Spacious w/Hot Tub, Fire Pit, Deck, Grill and WiFi
Fridge, microwave, oven, stovetop

*Modern Condo In Downtown Frederick*

*Modern Condo In Downtown Frederick*
Downtown Frederick
9.2 out of 10, Wonderful, (87 reviews)
"The location was perfect - walking distance to everything we wanted to do in Frederick. The place was clean and comfortable for 2 couples. "
United States
N. N.
The price is ￥12,646
￥36,253 total
includes taxes & fees
Apr 9 - Apr 10
*Modern Condo In Downtown Frederick*
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Shepherdstown Hotel Reviews

Hampton Inn Martinsburg

Hampton Inn Martinsburg

10/10 Excellent
"Retired couple. Love this place and stop here often - great staff, breakfast and convenience. Great stay every time. "
Samuel 1-night trip
Posted 5 hours ago
Hampton Inn Martinsburg

Find out more about Shepherdstown

Search for holiday rentals in Shepherdstown on Expedia! You can easily find your home rentals, villas, holiday apartments in Shepherdstown using one of the methods below:

  • View our selection of featured holiday rentals in Shepherdstown
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  • Enter your travel dates to view the best deals on holiday rentals in Shepherdstown while they last

Look no further and take a look at our great range of rental properties in Shepherdstown!

Frequently asked questions

Are there vacation rentals in Shepherdstown?

Yes, we have vacation rentals near well known local attractions in Shepherdstown, or you can go with a more secluded option if you want a relaxing place to stay. Nature enthusiasts will enjoy the riverfront in Shepherdstown. Make sure you have time to check out the university setting and gardens during your trip.

What's the top vacation rental in Shepherdstown?

Riverside cottage, minutes from historic Harpers Ferry! Private river access!: This vacation home rental near Shepherdstown offers a fireplace, a balcony, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals will I find in Shepherdstown?

Expedia has 10 vacation rentals for your stay in Shepherdstown.

What’s there to see and do in Shepherdstown?

Cultural attractions include Shepherdstown Opera House and Shepherdstown Museum, whereas Morgan's Grove Park is one spot to enjoy nature. While here, Shepherdstown Visitors Center and Rumsey Steamboat Museum are other places worth a visit.

What’s a vacation rental in Shepherdstown like?

Vacation rentals are private properties you can stay in for a couple of days or more in Shepherdstown. Vacation rentals feature amenities like kitchens and laundry facilities so you'll have everything you want. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from shared hotel elevators and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for a small group gathering.