Holiday Homes in Shepherdstown

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In one month
In two months
In three months

Featured Holiday Homes in Shepherdstown

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

10.0 out of 10, Exceptional, (70)
"The property was clean, quiet and the neighborhood was safe. We had a great time and tawny was a great host."
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, (188)
"Wonderful location near Antietam NP, Shepardstown, and Hagerstown. Small home but plenty of room. My family enjoyed their stay"
The price is NZ$288
includes taxes & fees
20 Oct - 21 Oct
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath

The Madison

10.0 out of 10, Exceptional, (36)
"The property was perfect. Beautiful place with a great location, offering everything you could possibly need or want. "
The Madison

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

10.0 out of 10, Exceptional, (132)
"Wonderful stay in a historic home within walking distance of so much American history and so many trails. Would definitely stay here again."
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!

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

9.8 out of 10, Exceptional, (147)
"Wonderful house for a great weekend away"
Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.

The Outpost: A Rustic Respite in the Shenandoah Valley 4 Bikes For Use Tesla Ch

8.8 out of 10, Excellent, (42)
"Great environment, lots to do within the area. Check in process is very convenient. Every room feels like a new adventure."
The Outpost: A Rustic Respite in the Shenandoah Valley 4 Bikes For Use Tesla Ch

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

10.0 out of 10, Exceptional, (19)
"We loved the night out at this property. A beautiful house in a great spot. The hosts were so accommodating and really friendly. "
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, (67)
"Great time. Everything was perfect and place was just what we needed. "
The price is NZ$466
includes taxes & fees
6 Oct - 7 Oct
*Luxury Condo In Downtown Frederick*

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

10.0 out of 10, Exceptional, (133)
"The property is wonderful! Very cozy and convenient to local attractions."
The price is NZ$423
includes taxes & fees
5 Oct - 6 Oct
Charming "Cream of the Crop" Cape ~❤️of Middletown

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

Waterfront property in Harpers Ferry - Private River Access

10.0 out of 10, Exceptional, (33)
"Enjoyable stay, lovely location Clean comfortable home."
Waterfront property in Harpers Ferry - Private River Access

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

9.4 out of 10, Exceptional, (106)
"Great little farm house in a quaint little town "
The price is NZ$499
includes taxes & fees
13 Oct - 14 Oct
Historic cozy farmhouse in the ❤️ of Myersville , MD close to Rt 70! Welcome Home

Camp Patowmack - Riverfront, Hot Tub, and Sauna!

9.6 out of 10, Exceptional, (4)
"This is a beautiful home in a secluded neighborhood with access to the Potomac River. The house is about 10 minutes from all of the things you would want to do in the Harper’s Ferry Historic area. The house is furnished and decorated very nicely and the kitchen has everything you will need for preparing & serving meals. It is a very peaceful location with lots of deer and opportunities to relax. "
The price is NZ$963
includes taxes & fees
20 Oct - 21 Oct
Camp Patowmack - Riverfront, Hot Tub, and Sauna!

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

2.0 star property
10.0 out of 10, Exceptional, (14)
"We really enjoyed the amenities and cleanliness of this location. The rental company was extremely communicative and responsive."
Trailblazer - hot tub, trail, game room, pets, wifi, fire pit, view, secluded

Sunlight 2BR townhouse w/ private parking in Downtown Frederick

9.4 out of 10, Exceptional, (24)
"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, (146)
"Charming, nicely restored log home in a great location for downtown. We would definitely stay here again! "
Gorgeous 1840 Log Cabin- Downtown

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

9.8 out of 10, Exceptional, (10)
"The fenced in yard was great for the dogs. The bed was comfortable. Close to Harper’s Ferry. Had a great stay. "
The price is NZ$627
includes taxes & fees
13 Oct - 14 Oct
A private home in historic Bolivar with a hot tub and yard. Pet friendly!

Cozy Cabin w/ Hot Tub, Arcade & Fire Pit perfect for up to 8 people

8.4 out of 10, Very good, (24)
"This house"
Cozy Cabin w/ Hot Tub, Arcade & Fire Pit perfect for up to 8 people

Stunning Views, Riverfront Privacy, 18-Acre Estate - Near Hikes, Wine/Breweries!

9.8 out of 10, Exceptional, (23)
"Most enjoyable two night stay. Wish we had the time to spend more time in this lovely house and properity."
Stunning Views, Riverfront Privacy, 18-Acre Estate - Near Hikes, Wine/Breweries!

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

9.8 out of 10, Exceptional, (125)
"Nice quaint cottage, perfect for our visit to the area. "
Riverside cottage, minutes from historic Harpers Ferry! Private river 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.
Save an average of 15% on thousands of hotels when you're signed in

Top Shepherdstown Hotel Reviews

Find out more about Shepherdstown

Find out more about Shepherdstown

Shepherdstown Holiday Homes information

Number of reviews
1,340
Accommodation
290 Holiday Homes
Lowest Price
NZ$288
Highest Price
NZ$963