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Check prices for these dates

Next weekend
Feb 7 - Feb 9
In two weeks
Feb 14 - Feb 16
In one month
Feb 28 - Mar 2
In two months
Mar 28 - Mar 30

Browse Select Shepherdstown Condo Rentals

*Modern Condo In Downtown Frederick*
Fridge, microwave, oven, stovetop

*Modern Condo In Downtown Frederick*

9.4 out of 10, Exceptional, (45)
"We will likely stay here again as it was a great deal for the space and location. It’s nice that they provide everything needed for a short term stay, you can tell there’s a lot of thought put into this place. Beds were pretty comfortable. Not really a complaint but just fyi that you can hear every step of whoever is staying upstairs. Our baby was able to sleep through it with his sound machine. "
The price is CA $153
CA $355 total
includes taxes & fees
Feb 3 - Feb 4
*Modern Condo In Downtown Frederick*
A newly renovated, pet-friendly Penthouse condo with private rooftop deck.
Miscellaneous

A newly renovated, pet-friendly Penthouse condo with private rooftop deck.

9.6 out of 10, Exceptional, (39)
"Clean with comfortable beds. Property was where we hoped. We had a wonderful time and walked everywhere.Be aware the furniture is on the smaller side. Either that or I am on the larger side. :)"
A newly renovated, pet-friendly Penthouse condo with private rooftop deck.
‘Slopeside Serenity' Mountain Condo: Steps to Lift
Terrace/patio

‘Slopeside Serenity' Mountain Condo: Steps to Lift

10.0 out of 10, Exceptional, (13)
"Quiet gateway"
‘Slopeside Serenity' Mountain Condo: Steps to Lift
Historic & Cozy ~ Near Antietam Battle & WhiteTail
Property grounds

Historic & Cozy ~ Near Antietam Battle & WhiteTail

10.0 out of 10, Exceptional, (26)
"Traveling from Illinois to New Hampshire for our road trip. This Vrbo in Hagerstown Maryland was in a beautiful historic district and the inside was absolutely beautiful. We did climb the 4 flights of stairs with 2 large suit cases which was not fun but it was a great way to stay in shape at 60 😂. Inside was so clean and adorable with the original floors, yet updated kitchen & living area. The bedrooms were very cozy and comfortable. The bathroom was large with a huge walk in shower and Amazing...
The price is CA $189
CA $372 total
includes taxes & fees
Feb 6 - Feb 7
Historic & Cozy ~ Near Antietam Battle & WhiteTail
Private Ground Level 2BR Condo
2 bedrooms, desk, iron/ironing board, free WiFi

Private Ground Level 2BR Condo

10.0 out of 10, Exceptional, (29)
"Had a great stay for christmas 2024. Very close to downtown area. "
Private Ground Level 2BR Condo
Accessible 1 bedroom apartment near downtown Frederick
Fridge, microwave, oven, stovetop

Accessible 1 bedroom apartment near downtown Frederick

Accessible 1 bedroom apartment near downtown Frederick
Upscale Walkup Apartment in the Heart of Historic Charles Town, WV
Interior

Upscale Walkup Apartment in the Heart of Historic Charles Town, WV

Upscale Walkup Apartment in the Heart of Historic Charles Town, WV
Ski and Hike From Front Stepsmountainside Getaway
Outdoor dining

Ski and Hike From Front Stepsmountainside Getaway

Ski and Hike From Front Stepsmountainside Getaway
Cozy, renovated Ski & Hiking Getaway - Whitetail
Sport court

Cozy, renovated Ski & Hiking Getaway - Whitetail

Cozy, renovated Ski & Hiking Getaway - Whitetail
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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Other property types in Shepherdstown

❤️ Secluded 1940s Romantic Tiny House on the River
Beach

❤️ Secluded 1940s Romantic Tiny House on the River

10.0 out of 10, Exceptional, (51)
"It was a cozy little tiny house located right on the river. I came in January and it was about 15 degrees outside so I did not get to use the outdoor shower or grill. I was able to enjoy the view of the river from the tiny house and walk outside on the road (not too many cars). If it was any warmer I would have built a fire and sat outside closer to the river. I would love to come back and stay when it was warmer to enjoy the outdoor more. Perfect retreat to reset. Very close to a nearby college...
The price is CA $64
CA $159 total
includes taxes & fees
Feb 17 - Feb 18
❤️ Secluded 1940s Romantic Tiny House on the River
Charming Cabin in the Woods with River Access
Exterior

Charming Cabin in the Woods with River Access

9.8 out of 10, Exceptional, (16)
"No central heating, bathroom fan couldn't be turned off, dinning room table light didn't work and front steps were not safe."
Charming Cabin in the Woods with River Access
Graycliff Hall: Riverfront Estate w/ Heli Pad, Private Chef, Hot Tub
Fridge, microwave, oven, stovetop

Graycliff Hall: Riverfront Estate w/ Heli Pad, Private Chef, Hot Tub

8.0 out of 10, Very good, (1)
"Our family had an unforgettable New Year's holiday at this incredible rental property! From the moment we arrived, we were amazed by the beautiful house, its spaciousness, and the plethora of facilities available to accommodate everyone in our group. The property was clean, well-organized, and tastefully decorated, making it a warm and inviting space for our celebration.The true gem of our stay was the exceptional hospitality provided by the property's management, especially the remarkable Miss...
Graycliff Hall: Riverfront Estate w/ Heli Pad, Private Chef, Hot Tub
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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What is there to do in Shepherdstown near my condo?
No matter your interests, Shepherdstown has plenty to keep you entertained. Shepherdstown Museum, Shepherdstown Opera House and Morgan’s Grove Park are on many travelers’ agendas. Don’t miss Cress Creek Golf Club, Shepherd University and Rumsey Monument either. With Expedia’s Shepherdstown condo deals, you can see more renowned attractions like these with the cash you save.