Search Vacation Homes in Shepherdstown

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Compare 248 Vacation Homes in Shepherdstown with updated reviews, rates, and availability.

Charming "Cream of the Crop" Cape ~❤️of Middletown
Property grounds
Charming "Cream of the Crop" Cape ~❤️of Middletown
10.0 out of 10, Exceptional, 102 reviews
"Cute cottage was clean and comfy. Everything you need to make a nice dinner, relax and enjoy the quiet neighborhood."
The price is $149
$314 total
includes taxes & fees
Jun 25 - Jun 26
Charming "Cream of the Crop" Cape ~❤️of Middletown
Riverside cottage, minutes from historic Harpers Ferry; private river access!
Property grounds
Riverside cottage, minutes from historic Harpers Ferry; private river access!
9.8 out of 10, Exceptional, 60 reviews
"Nice location for visiting Harpers Ferry. Great porch for watching the sunrise if you're up early."
The price is $145
$223 total
includes taxes & fees
Jul 1 - Jul 2
Riverside cottage, minutes from historic Harpers Ferry; private river access!
Hot Tub, Poker Table, River Access & Kayaks and Wineries
Smart TV, fireplace, table tennis, books
Hot Tub, Poker Table, River Access & Kayaks and Wineries
9.8 out of 10, Exceptional, 7 reviews
"Everything was fine."
The price is $167
$429 total
includes taxes & fees
Jul 2 - Jul 3
Hot Tub, Poker Table, River Access & Kayaks and Wineries
*Daley's Doll House At Antietam*
Property grounds
*Daley's Doll House At Antietam*
9.8 out of 10, Exceptional, 87 reviews
"My dog and I enjoyed the serenity and comfort of this adorable house."
*Daley's Doll House At Antietam*
Union Street Carriage Quarters
Exterior
Union Street Carriage Quarters
10.0 out of 10, Exceptional, 21 reviews
"This was our third stay here in a short period of time as our house gets renovated. We just love its coziness & cleanliness. Great communication with owners. Highly recommend!"
Union Street Carriage Quarters
Harpers Ferry Luxury, Spa Bathroom, Movie Room
Interior
Harpers Ferry Luxury, Spa Bathroom, Movie Room
9.6 out of 10, Exceptional, 9 reviews
"It was a nice stay. The area is great for walking. The venue was nice, just very vertical! Great communication with the host."
The price is $195
$369 total
includes taxes & fees
Jun 23 - Jun 24
Harpers Ferry Luxury, Spa Bathroom, Movie Room
Historic gem in the heart of downtown Hamilton! Trees and a private stream
Private kitchen
Historic gem in the heart of downtown Hamilton! Trees and a private stream
Historic gem in the heart of downtown Hamilton! Trees and a private stream
Charming Home with Yard Near Shenandoah River!
Fridge, microwave, stovetop, dishwasher
Charming Home with Yard Near Shenandoah River!
9.6 out of 10, Exceptional, 8 reviews
"We had a good time at the place. The big kitchen table is perfect for gathering when the weather keeps you from the fabulous fire pit. We would go back if we had an occasion to."
Charming Home with Yard Near Shenandoah River!
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
Exterior
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
10.0 out of 10, Exceptional, 93 reviews
"We enjoyed our stay at this historic home in the middle of town. We loved sitting on the porch and we slept great both nights."
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.
9.8 out of 10, Exceptional, 97 reviews
"The house was spotless was walking distance to everything we wanted to do. Would definitely coming back here to stay!"
Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.
Spacious Quiet Retreat with Hot Tub and Walk to River Minutes to Harpers Ferry
Terrace/patio
Spacious Quiet Retreat with Hot Tub and Walk to River Minutes to Harpers Ferry
9.8 out of 10, Exceptional, 8 reviews
"perfect # of bedrooms. Loved the hot tub. Would recommend the place to anyone traveling to the area."
Spacious Quiet Retreat with Hot Tub and Walk to River Minutes to Harpers Ferry
Hollow Hideaway is nestled between peaceful mountains and star filled skies
Property grounds
Hollow Hideaway is nestled between peaceful mountains and star filled skies
10.0 out of 10, Exceptional, 15 reviews
"We loved it! So clean, comfortable and beautiful! Close to parks and good hiking. Absolutely perfect."
Hollow Hideaway is nestled between peaceful mountains and star filled skies
Chic, pets, walk to downtown
Property grounds
Chic, pets, walk to downtown
10.0 out of 10, Exceptional, 4 reviews
"The house is immaculate, comfortable and super convenient! Access and location are perfect with many thoughtful touches that contribute to a restful stay. The outdoor space/patio is stunning and such a relaxing morning and evening spot for coffee or glass of wine (even when a crazy storm went through). Owners are very accessible and checked in often in case anything needed. Walk to downtown is lovely and easy to hop on routes to get anywhere. Thank you for a lovely Frederick stay while we...
Chic, pets, walk to downtown
Lake House w/ Pool and King Bed, Fishing - Dogs OK
Interior
Lake House w/ Pool and King Bed, Fishing - Dogs OK
10.0 out of 10, Exceptional, 12 reviews
"We enjoyed our stay, really nice place we enjoyed seeing the water"
Lake House w/ Pool and King Bed, Fishing - Dogs OK
Cozy home near Casino, Breweries, Historical attractions, National Park & more
Fridge, microwave, oven, stovetop
Cozy home near Casino, Breweries, Historical attractions, National Park & more
10.0 out of 10, Exceptional, 13 reviews
"We were in town for the comedy show at the casino. House was within walking distance however not a walk you would want to take wearing heels. Very quiet neighborhood with plenty of restaurants close by. The house was very clean and comfortable beds. Had a really great time!! Thank you!!!"
The price is $135
$288 total
includes taxes & fees
Jun 26 - Jun 27
Cozy home near Casino, Breweries, Historical attractions, National Park & more
White House Inn - Historic Home in Harpers Ferry!
Terrace/patio
White House Inn - Historic Home in Harpers Ferry!
10.0 out of 10, Exceptional, 17 reviews
"Cute Historical house with everything you need for a weekend away. Cooking pots are somewhat limited if planning on making a big meal, but for breakfast and normal meals is sufficient."
The price is $476
$931 total
includes taxes & fees
Jun 23 - Jun 24
White House Inn - Historic Home in Harpers Ferry!
River views, short walk to Harper Ferry, C&O Canal, and Appalachian trail.
Property grounds
River views, short walk to Harper Ferry, C&O Canal, and Appalachian trail.
9.0 out of 10, Wonderful, 4 reviews
"The house was clean; kitchen well-equipped; adequate parking; owner quickly responsed to a WIFI service provider problem; kids enjoyed the play area in yard; and we would stay here again, We recommend this property to others."
River views, short walk to Harper Ferry, C&O Canal, and Appalachian trail.
Walk to the canal and downtown!!! Cozy 1880 Fully Renovated townhome<br>
Fridge, microwave, oven, stovetop
Walk to the canal and downtown!!! Cozy 1880 Fully Renovated townhome<br>
10.0 out of 10, Exceptional, 47 reviews
"My friends and I stayed here for a weekend wedding. Not only is the location perfect but the attention to detail was great. Perfect for a small group or family."
Walk to the canal and downtown!!! Cozy 1880 Fully Renovated townhome<br>
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
Fridge, microwave, oven, stovetop
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
10.0 out of 10, Exceptional, 34 reviews
"The house was easy to coordinate, clean, and exactly as advertised. No issues at all."
The price is $145
$307 total
includes taxes & fees
Jun 16 - Jun 17
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
*Luxury Condo In Downtown Frederick*
Smart TV
*Luxury Condo In Downtown Frederick*
9.6 out of 10, Exceptional, 42 reviews
"It was beautiful and convenient"
The price is $200
$359 total
includes taxes & fees
Jun 16 - Jun 17
*Luxury Condo In Downtown Frederick*
Don't see what you're looking for?
See all available properties in Shepherdstown
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.

Other property types in Shepherdstown

❤️ Secluded 1940s Romantic Tiny House on the River
Beach
❤️ Secluded 1940s Romantic Tiny House on the River
10.0 out of 10, Exceptional, 41 reviews
"The tiny house is exactly as described. Its small, clean, cozy and comfortable. The location right on the river is fantastic. Being able to have a fire right by the water each night was such a plus. In better weather would be a great put in for canoeing, kataking. Very close many historic sights, unique shops, and outdoor activities. The hosts are very thoughtful, kind and responsive. We will be staying again!!"
The price is $75
$144 total
includes taxes & fees
Jun 23 - Jun 24
❤️ Secluded 1940s Romantic Tiny House on the River
Cozy Cottage
Exterior
Cozy Cottage
9.2 out of 10, Wonderful, 19 reviews
"Clean, quiet neighborhood, easy walk to downtown"
The price is $94
$213 total
includes taxes & fees
Jun 25 - Jun 26
Cozy Cottage
Plum Lazy on the Potomac
Property grounds
Plum Lazy on the Potomac
9.4 out of 10, Exceptional, 20 reviews
"My friends and I loved this house can’t wait to go back."
Plum Lazy on the Potomac
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.

Shepherdstown Vacation Homes information

Number of reviews
664
Accommodation
248 Vacation Homes
Lowest Price
$135
Highest Price
$476

Recent reviews of Shepherdstown hotels
Expedia verified reviews

Hampton Inn Hagerstown

Hampton Inn Hagerstown

5/5 Excellent
"this property was clean and comfortable. Staff was Welcoming and very attentive. I asked for an extra towel and they brought it to our room within minutes. our room was very comfortable. The only suggestion I have would be to fix the showerhead so that the water dispenses through the entire showerhead rather than the perimeter. Otherwise, a great property!"
A verified traveler stayed at Hampton Inn Hagerstown
Posted 1 day ago
Hampton Inn Hagerstown