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Check prices for these dates

Next weekend
28 Saf. - 2 Rab. I
In two weeks
7 Rab. I - 9 Rab. I
In one month
21 Rab. I - 23 Rab. I
In two months
18 Rab. II - 20 Rab. II

Compare 249 Vacation Homes in Shepherdstown with updated reviews, rates, and availability.

Trailside Retreat in breathtaking Western Loudoun
Exterior

Trailside Retreat in breathtaking Western Loudoun

10.0 out of 10, Exceptional, (44)
"We had a full family 4 day retreat and Jill’s place was perfect. Lots of room, beds were so comfy and contained all the kitchen and bathroom supplies we needed. Everything was clean - they even had some toys for the kids. Great location…convenient to all activities, restaurants and hiking trails. We would definitely book again. 5 stars!"
Trailside Retreat in breathtaking Western Loudoun
Gorgeous 1840 Log Cabin- Downtown
Family room a d dining area.

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
White House Inn - Historic Home in Harpers Ferry!
Aerial view

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 375
SAR 1,501 total
includes taxes & fees
23 Feb - 24 Feb
White House Inn - Historic Home in Harpers Ferry!
Riverside cottage, minutes from historic Harpers Ferry! Private river access!
Living Room

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

9.8 out of 10, Exceptional, (90)
"We had a wonderful stay at the Riverside cabin. With a beautiful view, perfect deck for reading, and a quiet house to get away in. So close to town and activities provided for a wonderful getaway. "
Riverside cottage, minutes from historic Harpers Ferry! Private river access!
Walk to Potomac River and downtown Harpers Ferry

Walk to Potomac River and downtown Harpers Ferry

10.0 out of 10, Exceptional, (111)
"The house was a perfect size for my group of 10. We stayed for my birthday weekend and the house was very stocked with cleaning supplies, sheets, pillows, towels, etc. Michael was very responsive and even sent a huge list of recommendations in the area. If I'm ever in the area again, I will definitely be staying here!!!"
Walk to Potomac River and downtown Harpers Ferry
Homey 'Ridgetop Retreat' - Walk to Hiking & Biking
Mercersburg Vacation Rental | 2BR | 1BA | 871 Sq Ft | 2 Steps Required for Entry

Homey 'Ridgetop Retreat' - Walk to Hiking & Biking

10.0 out of 10, Exceptional, (14)
"Cozy spot right by the slopes for easy access. Ski on, or a very short drive to main parking area. Bunk beds were great for the family. HVAC a bit noisy overnight, but overcame it with some white noise."
Homey 'Ridgetop Retreat' - Walk to Hiking & Biking
Charles Town Home w/ Private Pool & Hot Tub
Charles Town Vacation Rental | 5BR | 3.5BA | Stairs Required | 5,600 Sq Ft

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
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
View of High Street in Downtown Harpers Ferry from front porch

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

10.0 out of 10, Exceptional, (111)
"Great communication with host. Cosy house, well equipped kitchen in a great location."
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
*Luxury Condo In Downtown Frederick*
DINING ROOM - table for 4, back door to enter from the parking spots

*Luxury Condo In Downtown Frederick*

9.2 out of 10, Wonderful, (52)
"The condo was very good for the price and convenience. I think it definitely needs a little TLC with the furnishing and details. The communication for check-in was pretty poor and it took calling VRBO support to get our checkin instructions within 45 minutes of arrival after my messages were ignored for 2 days leading up to arrival. "
The price is SAR 383
SAR 890 total
includes taxes & fees
23 Feb - 24 Feb
*Luxury Condo In Downtown Frederick*
*In The Heart Of Antietam*
Exterior detail

*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*
Rural Home, Hot Tub, Campfire, Hardwood Floors
Exterior

Rural Home, Hot Tub, Campfire, Hardwood Floors

9.4 out of 10, Exceptional, (71)
"Lovely house. A couple of rooms were cold but not unbearably cold. The large table in the sun room was awesome for Thanksgiving dinner. We would definitely stay again if we wanted a house in the area."
Rural Home, Hot Tub, Campfire, Hardwood Floors
Spacious Quiet Retreat with Hot Tub and Walk to River Minutes to Harpers Ferry
Outdoor spa tub

Spacious Quiet Retreat with Hot Tub and Walk to River Minutes to Harpers Ferry

9.8 out of 10, Exceptional, (19)
"Family and friends surprised my sister for her 40th birthday with a weekend getaway. Host was very responsive and gave great recommendations. House is in a great location, everything was within 15-20 minutes away. Easy check-in process and very clean. Thanks again. "
Spacious Quiet Retreat with Hot Tub and Walk to River Minutes to Harpers Ferry
4BR, 4BA, Amazing Indoor Pool, EV charger, ~10 acres retreat, next to Park
Indoor Salt Pool

4BR, 4BA, Amazing Indoor Pool, EV charger, ~10 acres retreat, next to Park

10.0 out of 10, Exceptional, (29)
"The house is gorgeous. You walk through the front doors and immediately see the beautiful heated indoor pool. Our family had a blast in the pool and watching movies in the theater room. The host immediately responded to any questions that we had."
4BR, 4BA, Amazing Indoor Pool, EV charger, ~10 acres retreat, next to Park
Charming 3-Bedroom Home in historic Harpers Ferry: Pet Friendly!
Exterior

Charming 3-Bedroom Home in historic Harpers Ferry: Pet Friendly!

10.0 out of 10, Exceptional, (15)
"We loved our stay here and the property is simply delightful. It's central to all activities in Harper's Ferry, comfortable, well stocked and the host is super responsive! We especially loved the adjacent off-street parking, and although the weather didn't permit, the fenced, private outdoor space is very inviting. Our host was exceptionally responsive to the couple of questions we had and wonderful to work with. We'd definitely rent again! "
Charming 3-Bedroom Home in historic Harpers Ferry: Pet Friendly!
Private, Relaxing, quite, 3 Bedroom Unit, sleeps 6 to 8 people
Living area

Private, Relaxing, quite, 3 Bedroom Unit, sleeps 6 to 8 people

7.0 out of 10, Good, (7)
"This property met our needs beautifully. We will stay here again if we come back to the area, for sure"
The price is SAR 368
SAR 751 total
includes taxes & fees
1 Mar - 2 Mar
Private, Relaxing, quite, 3 Bedroom Unit, sleeps 6 to 8 people
“The Train Depot” 2nd oldest in the US
Exterior

“The Train Depot” 2nd oldest in the US

10.0 out of 10, Exceptional, (78)
"Great location in downtown Frederick. Cozy and comfortable accommodation with great historic vibes and modern amenities. We would definitely stay here again. "
“The Train Depot” 2nd oldest in the US
The Madison
Living area

The Madison

10.0 out of 10, Exceptional, (29)
"Fantastic. We loved it! "
The Madison
Woods Song - Natures Promise
Enjoy your favorite beverage on the enclosed porch.

Woods Song - Natures Promise

9.8 out of 10, Exceptional, (35)
"A great relaxing weekend."
Woods Song - Natures Promise
Romantic Stone Cottage Circa 1869-75 acres to Hike
Room

Romantic Stone Cottage Circa 1869-75 acres to Hike

9.2 out of 10, Wonderful, (5)
"Unfortunately we happened to stay when there was a wind storm in the county so we lost power, water and heat for the night. We texted the host to check on candles and/or flashlights but were told to “just use our phones”. (Not really an option when you’ve been traveling all day and phones are almost dead). The cottage is very rustic and not quite as comfortable as the pictures make it out to be. The bed is extremely firm so be aware if you have bad hips or back. There’s also glade plug ins in...
Romantic Stone Cottage Circa 1869-75 acres to Hike
Terra Alta - Incredible River Views and Hot Tub!
Soak in the tub while enjoying the beautiful view of the river below!

Terra Alta - Incredible River Views and Hot Tub!

9.8 out of 10, Exceptional, (54)
"Multiple generations enjoyed this lovely house with plenty of space, well stocked kitchen, and great location for winery visits. Highlights include extra sleeping space, local coffee provided by the host, and the hottub! Gorgeous views and responsive hosy! "
The price is SAR 375
SAR 1,499 total
includes taxes & fees
23 Feb - 24 Feb
Terra Alta - Incredible River Views and 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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Other property types in Shepherdstown

❤️ Secluded 1940s Romantic Tiny House on the River
Exterior

❤️ 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 165
SAR 411 total
includes taxes & fees
3 Mar - 4 Mar
❤️ 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, (17)
"Great experience. Cabin is as shown, very comfortable, easy access. 10 min to Shepherdstown, lots of great restaurants and shops there. Our dates ended up being over the severe cold/snow in January 2025, so we didn't do much hiking or anything on the river, but it was a lovely environment, very peaceful and cozy. Owners were super responsive when needed and very easy to work with. Would definitely go back in nicer weather! "
Charming Cabin in the Woods with River Access
Graycliff Hall: Riverfront Estate w/ Heli Pad, Private Chef, Hot Tub
Welcome To Graycliff Hall. Your beautiful riverside estate.

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.