
Holiday rentals in Shepherdstown
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Shepherdstown
Guests agree: these stays are highly rated for location, cleanliness and more.
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Popular amenities for Shepherdstown holiday rentals
Other great holiday rentals in Shepherdstown
Top guest favourite

Cabin in Great Cacapon
5 out of 5 average rating, 29 reviewsMountain/River View * Hot Tub * King
SamanthaRating, 5 stars5 days ago
Staying at Maureen’s was lovely, like staying at an old friend’s home. The view is amazing and surroundings are so peaceful. The decor is great and everything was easy to do. Make sure you download the entry instructions esp. the door entry pin before you arrive because the cell signal is non existent - or at least was for us. The WiFi however was awesome and I was able to do several video calls without interruption. I would stay here again in a second. We are grateful that Maureen and family decided to share their wonderful place with the world! Thank you!
Superhost

Flat in Downtown Frederick
5 out of 5 average rating, 3 reviewsCarroll Creek Charmer/ Sleeps 4 Luxurious King Bed
KarenRating, 5 stars1 day ago
This is the 5th Airbnb in downtown Frederick MD that we've stayed in within the past 6 months and we feel was the best. The only thing that could make it better would be private parking, but the property cannot accommodate that, so the hosts having a parking pass for the garage down the street is a good alternative. We rate this Airbnb as the best so far for decor inside & outside, accommodations (thanks for the coffee setup!), bed (a comfortable king), bath (best shower by far!) , and location. Terry was very detailed in instructions, and we appreciate that. Folks will enjoy their stay at Terry's place.
Guest favourite

Home in Cross Junction
4.87 out of 5 average rating, 124 reviewsThe Little Red Schoolhouse
JackelynRating, 5 stars1 week ago
Beautiful views and very peaceful to get away!
Guest favourite

Cabin in Berkeley Springs
5 out of 5 average rating, 24 reviewsGorgeous Log Chalet/Cabin with Hot Tub
ScottRating, 5 stars6 months ago
Great stay at a wonderful cabin nestled back into the woods. Well furnished and maintained with a phenomenal deck and screened patio.
Top guest favourite

Home in Berkeley Springs
5 out of 5 average rating, 25 reviewsMagic Mountain Retreat - Mountain View, EV charger
ScottRating, 5 stars3 months ago
Truly a beautiful home. Spotless, well-equipped, and perfectly maintained. Beautiful views of the mountains. Even though we were able to do less exploring and hiking in the area than we would have liked due to the snow and cold, we had a wonderful, cozy time up atop the hill there. (Rana warned us about the snow several days in advance, so we were mentally prepared). Hope to get back again sometime in spring, summer, or fall.
Top guest favourite

Home in Fairfield
4.96 out of 5 average rating, 72 reviewsTree Top Tranquility.
BrandiRating, 5 stars2 weeks ago
Amazing location in the mountains. Great location to everything we needed during our stay as we were back and forth to Gettysburg, Emmitsburg, Mount St. Mary and Thurmont. His home had everything we needed and more. We will definitely be back. Thank you very much for sharing your airbnb with our family.
Top guest favourite

Farm stay in Blue Ridge Summit
5 out of 5 average rating, 25 reviewsHistoric Stone Farmhouse-circa 1798
EmilyRating, 5 stars3 weeks ago
The property and home were charming. It was a unique and peaceful experience—would book again.
Guest favourite

Home in Smithsburg
5 out of 5 average rating, 9 reviewsEntire Mountain Cottage Near Scenic Hiking Trails
CatherineRating, 5 stars4 months ago
George was great to work with. House was clean, safe, and had lots of space for housing our extended family over Thanksgiving, with ample parking. It’s not an inexpensive option, but my family loved it and all were comfortable and happy!
Quick stats about holiday rentals in Shepherdstown
Total rentals
10 properties
Nightly prices starting at
£74 before taxes and fees
Total number of reviews
2.6K reviews
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
10 properties include access to wifi
Popular amenities
Self check-in, Gym and BBQ grill
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- Whitetail Resort
- Liberty Mountain Resort
- Caledonia State Park
- Cacapon Resort State Park
- Stone Tower Winery
- Gambrill State Park
- Great Falls Park
- Cunningham Falls State Park
- The Links at Gettysburg
- Congressional Country Club
- Columbia Country Club
- South Mountain State Park
- Robert Trent Jones Golf Club
- Twin Lakes Golf Course
- Shenandoah Valley Golf Club
- Notaviva Vineyards
- Whiskey Creek Golf Club
- Cowans Gap State Park
- Reston National Golf Course
- Chevy Chase Club
- Sly Fox Golf Club
- Bowling Green Country Club
- JayDee's Family Fun Center
- River Creek Club