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Vacation Homes in Shepherdstown

Our top choices for Shepherdstown vacation homes

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

10.0 out of 10, Exceptional, (66)
"We had a great time exploring Harper’s Ferry and loved having this as our home base!"
Walk to Harpers Ferry! Dog-friendly. Beautiful Views.

Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath

9.8 out of 10, Exceptional, (186)
"Wonderful location near Antietam NP, Shepardstown, and Hagerstown. Small home but plenty of room. My family enjoyed their stay"
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath

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

10.0 out of 10, Exceptional, (129)
"The property is wonderful! Very cozy and convenient to local attractions."
The price is AED 661
AED 1,234 total
includes taxes & fees
5 Oct - 6 Oct
Charming "Cream of the Crop" Cape ~❤️of Middletown

Charming 4-bedroom 1870 row house in Downtown Frederick Near Carroll Creek

Charming 4-bedroom 1870 row house in Downtown Frederick Near Carroll Creek

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

10.0 out of 10, Exceptional, (129)
"Place was nice and clean. Location was good. We enjoyed the quiet. Had a blast!"
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!

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

10.0 out of 10, Exceptional, (142)
"Wonderful house for a great weekend away"
The price is AED 713
AED 1,469 total
includes taxes & fees
8 Sep - 9 Sep
Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.

The Madison

10.0 out of 10, Exceptional, (35)
"We stayed for a week to tour college campuses for our son and are also considering moving there. We felt at home at The Madison and in the community. The house is exactly as described and in a great location to experience Frederick. "
The Madison

✨Luxurious Mountaintop Lodge🏔️ Scenic Views🫧Hot Tub under the BIG SKY STARS 🌟

10.0 out of 10, Exceptional, (42)
"Our fall getaway to Berkeley Springs was all the more enjoyable for our family with the beautiful view, hot tub, and game room!!"
✨Luxurious Mountaintop Lodge🏔️ Scenic Views🫧Hot Tub under the BIG SKY STARS 🌟

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

10.0 out of 10, Exceptional, (24)
"Perfect location. Very clean and well equipped. Comfortable beds and great shower. We enjoyed our stay very much "
The price is AED 750
AED 1,294 total
includes taxes & fees
8 Sep - 9 Sep
Charming 3-Bedroom Home in historic Harpers Ferry: Pet Friendly!

4 King Suites w/ Hot Tub, Fire Pit, Ping Pong, Arcade, Hi Speed Internet

10.0 out of 10, Exceptional, (16)
"The property was beyond my expectations, as a Combat veteran with Ptsd/TBI I found true peace and tranquillity here, I love the area, so much Military History! Close by, and definitely recommend this beautiful Home! Host was the best I have experienced,,, Thank you!"
4 King Suites w/ Hot Tub, Fire Pit, Ping Pong, Arcade, Hi Speed Internet

*Luxury Condo In Downtown Frederick*

9.0 out of 10, Wonderful, (66)
"The home was exactly as expected and made for a wonderful family/friend reunion! Perfect for socializing and so close to local shops and restaurants."
The price is AED 536
AED 1,133 total
includes taxes & fees
22 Sep - 23 Sep
*Luxury Condo In Downtown Frederick*

A private home in historic Bolivar with a hot tub and yard. Pet friendly!

9.8 out of 10, Exceptional, (8)
"The house was cute and just the right size for us. It was close to everything we wanted to see and do"
The price is AED 680
AED 1,252 total
includes taxes & fees
8 Sep - 9 Sep
A private home in historic Bolivar with a hot tub and yard. Pet friendly!

Historic cozy farmhouse in the ❤️ of Myersville , MD close to Rt 70! Welcome Home

9.4 out of 10, Exceptional, (103)
"Very nice old farm house with modern conveniences.. Comfortable and quiet. The antiques brought back memories of me visiting my grandparents back in the day. "
The price is AED 584
AED 1,086 total
includes taxes & fees
10 Sep - 11 Sep
Historic cozy farmhouse in the ❤️ of Myersville , MD close to Rt 70! Welcome Home

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

9.8 out of 10, Exceptional, (120)
"Very nice home with river access. Close to all area attractions."
Riverside cottage, minutes from historic Harpers Ferry! Private river access!

Terra Alta - Incredible River Views and Hot Tub!

9.6 out of 10, Exceptional, (58)
"We had a great time! The house overlooks the river and we loved the hot tub and fire pit! "
The price is AED 367
AED 1,480 total
includes taxes & fees
11 Sep - 12 Sep
Terra Alta - Incredible River Views and Hot Tub!

Trailblazer - hot tub, trail, game room, pets, wifi, fire pit, view, secluded

2.0 star property
10.0 out of 10, Exceptional, (13)
"I booked this place for a weekend getaway with family. The location was great, isolated enough, but close to Berkeley Spring and some nice trails. We enjoyed the amenities, view and the well stocked kitchen. "
Trailblazer - hot tub, trail, game room, pets, wifi, fire pit, view, secluded

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

10.0 out of 10, Exceptional, (74)
"The stay was great! The house was exactly as described. Danny was super responsive and accommodating. Overall would stay again!"
Walk to the canal and downtown!!! Cozy 1880 Fully Renovated townhome<br>

Main Street U.S.A. - Walk to Everything

8.0 out of 10, Very Good, (2)
"Location was perfect, the beds were very comfortable, and the house was lovely. The host was responsive and the check in/out couldn’t be easier. Two of the bedrooms and one of the bathrooms are accessed by passing through another bedroom which is a little awkward depending on who you are staying with. "
Main Street U.S.A. - Walk to Everything

Sunlight 2BR townhouse w/ private parking in Downtown Frederick

9.2 out of 10, Wonderful, (20)
"The location was perfect for walking just about anywhere we needed to go! Two bedrooms were a plus for me, my husband, and his sister. The half bath downstairs was also appreciated!"
Sunlight 2BR townhouse w/ private parking in Downtown Frederick

Gorgeous 1840 Log Cabin- Downtown

10.0 out of 10, Exceptional, (143)
"Charming, nicely restored log home in a great location for downtown. We would definitely stay here again! "
Gorgeous 1840 Log Cabin- Downtown
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