Holiday Homes in Shepherdstown

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Check prices for these dates

In two weeks
10 Oct - 12 Oct
In one month
24 Oct - 26 Oct
In two months
21 Nov - 23 Nov
In three months
19 Dec - 21 Dec

Featured Holiday Homes in Shepherdstown

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

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

10.0 out of 10, Exceptional, (69)
"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
Property grounds

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

9.8 out of 10, Exceptional, (187)
"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
The Madison
Dining

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!
Exterior detail

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.
Exterior

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

10.0 out of 10, Exceptional, (146)
"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
Outdoor dining

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
Exterior

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*
Smart TV

*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 AU$414
includes taxes & fees
29 Sept - 30 Sept
*Luxury Condo In Downtown Frederick*
Charming "Cream of the Crop" Cape ~❤️of Middletown
Terrace/patio

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 AU$380
includes taxes & fees
1 Oct - 2 Oct
Charming "Cream of the Crop" Cape ~❤️of Middletown
✨Luxurious Mountaintop Lodge🏔️ Scenic Views🫧Hot Tub under the BIG SKY STARS 🌟
Outdoor dining

✨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 🌟
Waterfront property in Harpers Ferry - Private River Access
Property grounds

Waterfront property in Harpers Ferry - Private River Access

10.0 out of 10, Exceptional, (32)
"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
Fridge, microwave, oven, stovetop

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

9.4 out of 10, Exceptional, (105)
"Great little farm house in a quaint little town "
The price is AU$449
includes taxes & fees
9 Oct - 10 Oct
Historic cozy farmhouse in the ❤️ of Myersville , MD close to Rt 70! Welcome Home
Camp Patowmack - Riverfront, Hot Tub, and Sauna!
Outdoor dining

Camp Patowmack - Riverfront, Hot Tub, and Sauna!

9.4 out of 10, Exceptional, (3)
"We thoroughly enjoyed this property. It is a beautiful cabin located directly on the Potomac river near Harpers Ferry. We would stay here again. It has everything you could possibly need for a quiet escape! "
The price is AU$817
includes taxes & fees
1 Oct - 2 Oct
Camp Patowmack - Riverfront, Hot Tub, and Sauna!
Trailblazer - hot tub, trail, game room, pets, wifi, fire pit, view, secluded
Terrace/patio

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

2.0 star property
10.0 out of 10, Exceptional, (13)
"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
Fridge, microwave, oven, stovetop

Sunlight 2BR townhouse w/ private parking in Downtown Frederick

9.4 out of 10, Exceptional, (23)
"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
Fridge, microwave, oven, stovetop

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!
Smart TV, fireplace

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

9.8 out of 10, Exceptional, (9)
"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 AU$490
includes taxes & fees
29 Sept - 30 Sept
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
Outdoor dining

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!
Terrace/patio

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!
Terrace/patio

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

9.8 out of 10, Exceptional, (124)
"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.
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Top Shepherdstown Hotel Reviews

Holiday Inn Express Charles Town by IHG

Holiday Inn Express Charles Town by IHG

10/10 Excellent
"The hotel is very clean and comfortable. The breakfast is good and the shuttle service is very convenient and was a nice surprise (they'll take you anywhere within 2 miles and pick you up). The staff was all very nice and helpful. "
Melissa 2-night trip
Posted 2 days ago
Holiday Inn Express Charles Town by IHG

Find out more about Shepherdstown

Find out more about Shepherdstown

Shepherdstown Holiday Homes information

Number of reviews
1,328
Accommodation
309 Holiday Homes
Lowest Price
AU$380
Highest Price
AU$817

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