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Compare 305 Vacation Homes in Shepherdstown with updated reviews, rates, and availability.

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

10.0 out of 10, Exceptional, (122)
"Visited nice restaurants, brew pubs, antique shops. House was perfect for us. Very clean and well equipped. "
The price is SAR 375
SAR 934 total
includes taxes & fees
23 Mar - 24 Mar
Charming "Cream of the Crop" Cape ~❤️of Middletown

*Luxury Condo In Downtown Frederick*

9.0 out of 10, Wonderful, (55)
"The condo is quite spacious, more than expected. We enjoyed the modern touches and private parking is a big plus in downtown Frederick. So close to Carroll Creek and Market St. The hosts are responsive. We highly recommend staying at Gideon Getaways! "
The price is SAR 383
SAR 895 total
includes taxes & fees
23 Mar - 24 Mar
*Luxury Condo In Downtown Frederick*

Riverside cottage, minutes from historic Harpers Ferry! Private river access!

9.8 out of 10, Exceptional, (92)
"We enjoyed a very comfortable stay. House was very clean and cozy. We were a little surprised by the close proximity to other homes, but other than that it was as described. Hosts were easy to communicate with and created a very welcoming space for us. Thank you! "
Riverside cottage, minutes from historic Harpers Ferry! Private river access!

Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!

10.0 out of 10, Exceptional, (113)
"My husband and I thoroughly enjoyed staying in Harper's Ferry. It is a beautiful historic town with many sights to see. This house made it very convenient to have quick access to everything. It was especially useful for time management. We were able to complete our full itinerary that we had planned in advance."
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!

*In The Heart Of Antietam*

9.6 out of 10, Exceptional, (82)
"House is clean, pleasant with comfortable beds, a serviceable kitchen and nice common space. My husband and 2 adult children were visiting family who live in sharpsburg and their house was pretty full with other visitors. This was a perfect place for us. Highly recommend. "
*In The Heart Of Antietam*

Trailside Retreat in breathtaking Western Loudoun

10.0 out of 10, Exceptional, (45)
"The houses wonderfully decorated and super clean. Has many amenities. It’s very convenient if you’re visiting Leesburg. Lots of awesome restaurants in the general vicinity and interesting historical sites."
Trailside Retreat in breathtaking Western Loudoun

Walk to Harpers Ferry! Dog-friendly. Beautiful Views.

10.0 out of 10, Exceptional, (43)
"Townhome was in a very convenient location, nicely stocked, roomy, and very comfortable. Communication was fast, friendly and helpful. We came for a girls' weekend and left wanting to come back again soon! No complaints. We'd definitely stay here again and were happy to support a Veteran family!"
Walk to Harpers Ferry! Dog-friendly. Beautiful Views.

Charles Town Home w/ Private Pool & Hot Tub

10.0 out of 10, Exceptional, (41)
"Our families decided to rent the property for a getaway close to the DMV. It was easy to check in, get around Charles Town and enjoy the property. Even with an unexpected 6" of snow, we still found time to appreciate everything the property had to offer."
Charles Town Home w/ Private Pool & Hot Tub

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

9.4 out of 10, Exceptional, (104)
"We loved the historic home and its proximity to Carroll Creek and shopping! We were in town for a wedding and were able to walk everywhere we needed to go. "
The price is SAR 499
SAR 1,145 total
includes taxes & fees
24 Mar - 25 Mar
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

“The Train Depot” 2nd oldest in the US

10.0 out of 10, Exceptional, (79)
"Inside was updated. Loved the open space. Good location though it was a drive to downtown shopping and eating. I would stay there again. "
“The Train Depot” 2nd oldest in the US

Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.

9.8 out of 10, Exceptional, (124)
"We traveled with a couple who are good friends to celebrate my upcoming birthday. Visiting Harpers Ferry in the winter was a good decision, because it wasn't crowded yet most everything was open. Breweries and wineries and museums. . . it was a great trip! The home is beautiful and very thoughtfully restored. The owner even won a preservation award for the house and it's richly deserved! The kitchen is well stocked and everything was just comfortable. It was a great place from which to explore...
Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.

Indulge in Elegance: 7 BR Manor with Events in Historic Waterford

Indulge in Elegance: 7 BR Manor with Events in Historic Waterford

Luxury Getaway on The Potomac

9.6 out of 10, Exceptional, (7)
"My group of friends have started to do an annual getaway trip. This location worked best because of the group size we had, as well as its location being a reasonable distance from where we all live. It lived up to our expectations and and then some! The house was very well maintained and clean and everything was pretty well stocked up in the kitchen as well. Everyone who came loved the home and Melissa was an excellent host. She was very responsive and addressed all of my questions with a prompt...
Luxury Getaway on The Potomac

Walk to the canal and downtown!!! Cozy 1880 Fully Renovated townhome<br>

10.0 out of 10, Exceptional, (65)
"Danny sent recommendations and was very kind and communicative both before and during our stay. The place was SO cute, and I’d absolutely consider coming back, as this was more of a staycation (I live in DC). Definitely recommend staying here!"
Walk to the canal and downtown!!! Cozy 1880 Fully Renovated townhome<br>

Hot Tub, Game Room, River Access, Fire Pit & Grill

9.6 out of 10, Exceptional, (22)
"This was a perfect place for our group. Bedroom for everyone, up and down tvs for movie and sports watching, table for gaming, and hrs in the hot tub. Dining table was big enough for everyone to eat together, and the kitchen had what we needed to manage all our meals"
The price is SAR 792
SAR 1,433 total
includes taxes & fees
31 Mar - 1 Apr
Hot Tub, Game Room, River Access, Fire Pit & Grill

Spacious estate in charming Purcellville with WiFi, fitness room, AC

2.0 star property
10.0 out of 10, Exceptional, (3)
"Beautiful countryside, great selection of local wineries and accessible to West Virginia, this property is hard to beat."
Spacious estate in charming Purcellville with WiFi, fitness room, AC

Wine Weekend Getaway: Steps to Winery & Battlefield w/ Mountain Views & Hot Tub!

10.0 out of 10, Exceptional, (27)
"It is a cute house out in the country. Loved being away from town just like our home"
The price is SAR 675
SAR 1,424 total
includes taxes & fees
13 Apr - 14 Apr
Wine Weekend Getaway: Steps to Winery & Battlefield w/ Mountain Views & Hot Tub!

White House Inn - Historic Home in Harpers Ferry!

10.0 out of 10, Exceptional, (28)
"We very much enjoyed our stay at this property. Walking distance to Harper's ferry attractions and plenty of room for 5 adults to spread out. We anticipate renting this property in the future for more ladies weekends!"
The price is SAR 491
SAR 1,694 total
includes taxes & fees
24 Mar - 25 Mar
White House Inn - Historic Home in Harpers Ferry!

Gorgeous 1840 Log Cabin- Downtown

10.0 out of 10, Exceptional, (125)
"This cabin was easy to find, with off-street parking, and near the beautiful downtown area. I travelled with individuals with disabilities and found the spacious layout very accommodating to our needs. The bathrooms, common room, kitchen, and bedrooms gave it the cabin vibe, were comfortable, and had everything we could possibly need. The host was available for any feedback and I would highly recommend this location for families or friends looking to stay in Frederick. "
Gorgeous 1840 Log Cabin- Downtown

Peaceful & Secluded Knoxville Retreat w/ Deck

10.0 out of 10, Exceptional, (38)
"very cute house in the woods not missing anything. Hosts were very friendly and responsive. Perfect for a weekend getaway. We would stay again"
Peaceful & Secluded Knoxville Retreat w/ Deck
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

10.0 out of 10, Exceptional, (53)
"The cabin was perfect for a few days of writing and reflecting! Everything was very clean and it was easy communicating with the owner. The house is not "secluded" as there are neighboring houses on two sides and if I hadn't brought an ax/saw to cut my own dry wood enjoying a fire wouldn't have been possible. But overall a lovely stay and I look forward to going again!"
The price is SAR 270
SAR 529 total
includes taxes & fees
30 Mar - 31 Mar
❤️ Secluded 1940s Romantic Tiny House on the River

Charming Cabin in the Woods with River Access

9.8 out of 10, Exceptional, (18)
"Perfect couples get away!"
The price is SAR 581
SAR 1,070 total
includes taxes & fees
17 Apr - 18 Apr
Charming Cabin in the Woods with River Access

Welcome to this patch of serenity on the river's edge, to this hideaway.

9.8 out of 10, Exceptional, (60)
"Loved everything. Quiet, peaceful….loved the small deck off the upstairs bedroom."
Welcome to this patch of serenity on the river's edge, to this hideaway.
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.