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Our top choices for Shepherdstown vacation homes

10.0 out of 10, Exceptional, (10)
"This property was super nice and the property managers were super awesome and accommodating! "
United States
Construction V.
The price is AED 1,284
AED 2,161 total
includes taxes & fees
11 Jan - 12 January 2026
Exclusive Wooded Chalet w Magnificent River Views
2.0 star property
10.0 out of 10, Exceptional, (1)
"The home was perfect for our visit.We were in and out all weekend but really appreciated the well stocked kitchen supplies, the comfortable beds and the hot water levels. We were able to relax in the spacious living room and spend some time on the little outdoor areas. We would stay again but if the group was much bigger there may be issues as there are only bathrooms on the first floor. "
United States
Erin J.
New, Contemporary House in Historic Harpers Ferry
10.0 out of 10, Exceptional, (139)
"Love the place will book again"
United States
WAYNE M.
The price is AED 459
AED 1,032 total
includes taxes & fees
14 Dec - 15 Dec
Charming "Cream of the Crop" Cape ~❤️of Middletown
9.4 out of 10, Exceptional, (119)
"We loved being so close to all the action downtown. A perfect getaway for our family to explore the area, visit with family, and eat great food!!! "
United States
Natalie C.
The price is AED 408
AED 1,016 total
includes taxes & fees
16 Dec - 17 Dec
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

Vacation Home in Downtown Frederick

*Luxury Condo In Downtown Frederick*
9.0 out of 10, Wonderful, (71)
"Great time. Everything was perfect and place was just what we needed. "
United States
dominick c.
The price is AED 375
AED 954 total
includes taxes & fees
14 Dec - 15 Dec
*Luxury Condo In Downtown Frederick*
6.0 out of 10, (1)
"The inside was very clean, outside was a mess. Location was bad, on a busy street and a busy railway."
United States
mark C.
The price is AED 404
AED 783 total
includes taxes & fees
12 Dec - 13 Dec
3-bedroom townhome in charming Hagerstown with AC, WiFi
10.0 out of 10, Exceptional, (5)
"Great and quiet location with all the amenities. Getting to the parking is a bit tricky but other than that great place to stay with family"
United States
Vinod B.
The price is AED 294
AED 1,115 total
includes taxes & fees
15 Dec - 16 Dec
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!
10.0 out of 10, Exceptional, (3)
"The location was great and the host was very east to communicate with."
United States
Liz B.
The price is AED 585
AED 1,400 total
includes taxes & fees
15 Dec - 16 Dec
Historic Queen Anne Family Home w Modern Comforts
9.8 out of 10, Exceptional, (58)
"We loved visiting! Wish we could've stayed longer. The accommodations were great; super comfortable and inviting. Everyone enjoyed themselves. Thanks for having us!"
United States
David F.
The price is AED 459
AED 1,032 total
includes taxes & fees
17 Dec - 18 Dec
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

Vacation Home in Berkeley Springs

Modern, family-friendly, nature packed getaway
9.2 out of 10, Wonderful, (19)
"Great house! We loved the fire pit outside and the beautiful interior. Host was very responsive and helpful! Would def stay here again. "
United States
Erika R.
The price is AED 459
AED 994 total
includes taxes & fees
12 Dec - 13 Dec
Modern, family-friendly, nature packed getaway
10.0 out of 10, Exceptional, (34)
"Two bedroom each with its own bathroom was so nice for our small group. The apartment is walking distance to town and in a quiet neighborhood. Our stay was perfect!"
United States
Jennifer S.
The price is AED 404
AED 965 total
includes taxes & fees
4 Jan - 5 January 2026
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
10.0 out of 10, Exceptional, (38)
"Very clean and well appointed. Great for a large group. "
United States
Richard
White House Inn - Historic Home in Harpers Ferry!
9.4 out of 10, Exceptional, (110)
"Alot of choices for food and snacks within walking distance. "
United States
Cherilyn H.
The price is AED 584
AED 1,086 total
includes taxes & fees
17 Dec - 18 Dec
Historic cozy farmhouse in the ❤️ of Myersville , MD close to Rt 70! Welcome Home
9.4 out of 10, Exceptional, (19)
"A nice relaxing place to stay in the mountains of WV near many things to do. Check-in and check-out instructions were easy to follow. "
United States
L G.
The price is AED 610
AED 1,574 total
includes taxes & fees
12 Dec - 13 Dec
Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry
8.0 out of 10, Very Good, (1)
"This was a great location for two families coming together for a wedding. The beds were comfortable, and the house was conveniently located within walking distance of a shopping plaza and close to the expressway on-ramp. The owner was quick to respond and helpful in answering any questions we had.Overall, the house met all our needs and provided a comfortable stay. It could use a few minor updates—like fresh paint on the scuffed walls—and some additional seating since it sleeps nine people....
United States
Heather P.
The price is AED 507
AED 1,265 total
includes taxes & fees
14 Dec - 15 Dec
Easy Self Check-in 4BR Escape • Prime Walkable Location • Dining & Shops Nearby
9.6 out of 10, Exceptional, (65)
"It was a great house for a weekend getaway. Most of the house was clean. The exterior was a little unkept. A few repairs would be good for the exterior. Everything was functional. The bed was great. Hot tub was clean and well maintained. The grill was like new and worked well. I would stay here again. "
United States
Lance B.
The price is AED 367
AED 1,476 total
includes taxes & fees
22 Dec - 23 Dec
Terra Alta - Incredible River Views and Hot Tub!
9.4 out of 10, Exceptional, (3)
"Property was very clean and accurate of listing description. cell phone service was rough however internet in house was never an issue. House is in good shape. Owner was quick to respond once receiving text message. Email is best way to communicate. you do have a lil drive into town if you need something however that was not an issue with us and the location is what we were looking for. Would 100% stay again if in the area"
United States
Kevin W.
The price is AED 698
AED 1,925 total
includes taxes & fees
15 Dec - 16 Dec
4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline
The price is AED 367
AED 1,385 total
includes taxes & fees
14 Dec - 15 Dec
Riverview Retreat - Pool, Hot Tub, and Mtn Views!
10.0 out of 10, Exceptional, (21)
"Great stay, super nice people and wonderful house."
United States
Kenzie S.
The price is AED 591
AED 1,810 total
includes taxes & fees
16 Dec - 17 Dec
4 King Suites w/ Hot Tub, Fire Pit, Ping Pong, Arcade, Hi Speed Internet
8.6 out of 10, Excellent, (10)
"We had an amazing stay at your cabin! It was just what we were hoping for. The neighborhood is nicely spread out, giving the kids lots of space to roam and explore. The beds were super comfortable, and the kitchen had everything we needed to cook our meals. Communication with the host was excellent, and we really appreciated the guest passes to the sports center. We’d love to return again soon!"
United States
Jamie W.
The price is AED 573
AED 1,140 total
includes taxes & fees
17 Dec - 18 Dec
Modern Cabin w Hot Tub & Indoor Pool/Gym Access!
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