Holiday Homes in Shepherdstown

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Our top choices for Shepherdstown holiday homes

Exclusive Wooded Chalet w Magnificent River Views

Exclusive Wooded Chalet w Magnificent River Views
Shepherdstown
10.0 out of 10, Exceptional, (12 reviews)
"This property was super nice and the property managers were super awesome and accommodating! "
United States
Construction V.
Exclusive Wooded Chalet w Magnificent River Views

*Luxury Condo In Downtown Frederick*

*Luxury Condo In Downtown Frederick*
Downtown Frederick
9.0 out of 10, Wonderful, (77 reviews)
"Lovely place. It was perfect for our girls' trip long weekend. The rooms were so spacious and tastefully decorated. It was also super clean and had everything we needed, including for our night staying in with Door-dash to binge watch a couple Netflix series. The coffee lover in our group was so appreciative of the supplies and setup. The location is fabulous for walking the Creek Park, or to dinning and shopping options. We're looking forward to making this our Christmas present to each other...
United States
Lynne
The price is €221
includes taxes & fees
1 Feb - 2 Feb
*Luxury Condo In Downtown Frederick*

Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick

Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
Frederick
10.0 out of 10, Exceptional, (35 reviews)
"Two bedroom each with its own bathroom was so nice for our small group. The apartment is walking distance to town and in a quiet neighborhood. Our stay was perfect!"
United States
Jennifer S.
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick

4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline

4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline
Harpers Ferry
9.4 out of 10, Exceptional, (3 reviews)
"Property was very clean and accurate of listing description. cell phone service was rough however internet in house was never an issue. House is in good shape. Owner was quick to respond once receiving text message. Email is best way to communicate. you do have a lil drive into town if you need something however that was not an issue with us and the location is what we were looking for. Would 100% stay again if in the area"
United States
Kevin W.
The price is €330
includes taxes & fees
18 Feb - 19 Feb
4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline

Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!
Harpers Ferry
10.0 out of 10, Exceptional, (7 reviews)
"Great and quiet location with all the amenities. Getting to the parking is a bit tricky but other than that great place to stay with family"
United States
Vinod B.
The price is €378
includes taxes & fees
2 Mar - 3 Mar
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
Jefferson
9.8 out of 10, Exceptional, (58 reviews)
"The beds were incredibly comfortable. Great house. Great location. "
United States
Julie B.
The price is €305
includes taxes & fees
2 Mar - 3 Mar
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

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

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (142 reviews)
"Love the place will book again"
United States
WAYNE M.
The price is €233
includes taxes & fees
2 Feb - 3 Feb
Charming "Cream of the Crop" Cape ~❤️of Middletown

Camp Patowmack - Riverfront, Hot Tub, and Sauna!

Camp Patowmack - Riverfront, Hot Tub, and Sauna!
Harpers Ferry
9.8 out of 10, Exceptional, (6 reviews)
"Great house with a beautiful view. "
United States
Sandra A.
The price is €461
includes taxes & fees
5 Feb - 6 Feb
Camp Patowmack - Riverfront, Hot Tub, and Sauna!

Riverview Retreat - Pool, Hot Tub, and Mtn Views!

Riverview Retreat - Pool, Hot Tub, and Mtn Views!
Harpers Ferry
10.0 out of 10, Exceptional, (1 review)
"We had a great time at Riverview Retreat! The house was perfect for our group and offered beautiful views. We especially loved the fireplace and all of the amenities they had available. The hot tub code was missing from the manual so we weren't able to use it on our first night and the spiral staircase was pretty intimidating for the weather we had. Heed the warnings about needing four wheel drive in the winter for the driveway. I was thankful there wasn't snow as it would have been scary to...
United States
Stacy H.
The price is €345
includes taxes & fees
10 Feb - 11 Feb
Riverview Retreat - Pool, Hot Tub, and Mtn Views!

3-bedroom townhome in charming Hagerstown with AC, WiFi

3-bedroom townhome in charming Hagerstown with AC, WiFi
Hagerstown
7.6 out of 10, Good, (4 reviews)
"Clean and comfy. "
United States
Nicola S.
The price is €181
includes taxes & fees
2 Feb - 3 Feb
3-bedroom townhome in charming Hagerstown with AC, WiFi

Terra Alta - Incredible River Views and Hot Tub!

Terra Alta - Incredible River Views and Hot Tub!
Charles Town
9.6 out of 10, Exceptional, (66 reviews)
"Nice quiet view, able to sit on deck for hours and talk. Close to restaurants, and stores. Had a great stay."
United States
Paul M.
The price is €336
includes taxes & fees
5 Feb - 6 Feb
Terra Alta - Incredible River Views and Hot Tub!

Cozy Hidden Cabin 7 Mins To Town With Parking

Cozy Hidden Cabin 7 Mins To Town With Parking
Harpers Ferry
10.0 out of 10, Exceptional, (10 reviews)
"The home was clean and beautifully decorated. "
United States
Preeti r.
The price is €305
includes taxes & fees
2 Feb - 3 Feb
Cozy Hidden Cabin 7 Mins To Town With Parking

Modern luxury, walk to Washington St and downtown, EV, Movie room, Spa bathroom

Modern luxury, walk to Washington St and downtown, EV, Movie room, Spa bathroom
Bolivar
10.0 out of 10, Exceptional, (37 reviews)
"Great property and a short distance from historic Harper’s Ferry! "
United States
Mike M.
The price is €251
includes taxes & fees
1 Feb - 2 Feb
Modern luxury, walk to Washington St and downtown, EV, Movie room, Spa bathroom

NEW! Ferrystone Lodge: Mountain Retreat w/ Patio & Fireplace

NEW! Ferrystone Lodge: Mountain Retreat w/ Patio & Fireplace
Harpers Ferry
10.0 out of 10, Exceptional, (7 reviews)
The price is €289
includes taxes & fees
1 Feb - 2 Feb
NEW! Ferrystone Lodge: Mountain Retreat w/ Patio & Fireplace

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

4 King Suites w/ Hot Tub, Fire Pit, Ping Pong, Arcade, Hi Speed Internet
Knoxville
10.0 out of 10, Exceptional, (22 reviews)
"Great stay, super nice people and wonderful house."
United States
Kenzie S.
The price is €417
includes taxes & fees
1 Feb - 2 Feb
4 King Suites w/ Hot Tub, Fire Pit, Ping Pong, Arcade, Hi Speed Internet

Modern Suite with Private Bath – Stylish & Comfy

Modern Suite with Private Bath – Stylish & Comfy
Frederick
Modern Suite with Private Bath – Stylish & Comfy

Historic Queen Anne Family Home w Modern Comforts

Historic Queen Anne Family Home w Modern Comforts
Harpers Ferry
10.0 out of 10, Exceptional, (4 reviews)
"The location was great and the host was very east to communicate with."
United States
Liz B.
The price is €305
includes taxes & fees
1 Feb - 2 Feb
Historic Queen Anne Family Home w Modern Comforts

Mountain Retreat w 2 Living Spaces & Scenic Deck

Mountain Retreat w 2 Living Spaces & Scenic Deck
Harpers Ferry
The price is €259
includes taxes & fees
2 Feb - 3 Feb
Mountain Retreat w 2 Living Spaces & Scenic Deck

Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC

Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
Rohrersville
10.0 out of 10, Exceptional, (6 reviews)
"Beautiful setting with wonderful indoor and outdoor spaces. The house is charming, renovated, updated, clean, and comfortable. Great location for a family gathering to bike, visit the battlefield or visit Shepherdstown. Hosts went above and beyond to be sure we had all we needed. Would definitely stay again if in the area. "
United States
Christopher R.
The price is €353
includes taxes & fees
6 Feb - 7 Feb
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC

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

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Downtown Frederick
9.4 out of 10, Exceptional, (120 reviews)
"Great location — right on the Carroll Creek Walk and a stone’s throw from excellent restaurants and nice shops. "
United States
Darby R.
The price is €279
includes taxes & fees
2 Feb - 3 Feb
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
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

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Shepherdstown Holiday Homes information

Number of reviews
600
Accommodation
281 Holiday Homes
Lowest Price
€181
Highest Price
€461