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Vacation Homes in Shepherdstown

Exclusive Wooded Chalet w Magnificent River Views

10.0 out of 10, Exceptional, (6)
"This property was super nice and the property managers were super awesome and accommodating! "
Exclusive Wooded Chalet w Magnificent River Views

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

10.0 out of 10, Exceptional, (52)
"Very conveniently located for our visit with an amazing bakery and awesome meat market across the street. "
The price is SAR 371
SAR 951 total
includes taxes & fees
9 Sep - 10 Sep
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

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

10.0 out of 10, Exceptional, (130)
"The property is wonderful! Very cozy and convenient to local attractions."
The price is SAR 356
SAR 931 total
includes taxes & fees
9 Sep - 10 Sep
Charming "Cream of the Crop" Cape ~❤️of Middletown

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

9.4 out of 10, Exceptional, (115)
"This property is perfectly situated if your goal is to be able to walk through Frederick and enjoy the parks, shopping, and restaurants"
The price is SAR 458
SAR 1,098 total
includes taxes & fees
14 Sep - 15 Sep
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry

2.0 star property
9.8 out of 10, Exceptional, (9)
"Great place and good location."
Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry

Lakefront House w/ Modern Comforts!

8.8 out of 10, Excellent, (3)
"The house is lovely. Very much enjoyed the stay. Looking forward to going back!!"
The price is SAR 375
SAR 1,324 total
includes taxes & fees
11 Sep - 12 Sep
Lakefront House w/ Modern Comforts!

Kalia’s Mountain Momma Getaway

10.0 out of 10, Exceptional, (11)
"Location was nice"
The price is SAR 409
SAR 664 total
includes taxes & fees
14 Sep - 15 Sep
Kalia’s Mountain Momma Getaway

Wine Weekend Getaway: Steps to Winery & Battlefield w/ Mountain Views & Hot Tub!

10.0 out of 10, Exceptional, (36)
"It is a cute house out in the country. Loved being away from town just like our home"
The price is SAR 582
SAR 1,332 total
includes taxes & fees
5 Oct - 6 Oct
Wine Weekend Getaway: Steps to Winery & Battlefield w/ Mountain Views & Hot Tub!

Chic, pets, walk to downtown

10.0 out of 10, Exceptional, (13)
"Beautiful home with all desired ammenaties and very professional owners"
The price is SAR 847
SAR 1,462 total
includes taxes & fees
19 Sep - 20 Sep
Chic, pets, walk to downtown

Chic Spacious Home 5 Mins To College & Frederick Health

10.0 out of 10, Exceptional, (1)
"The homeowners are the nicest people I’ve ever met. Super friendly and responsive. I would stay here every single time. Home is beautiful and placed in the heart of Frederick so everything is a walking distance. And there’s no street parking!!!!! That’s definitely an added plus. "
Chic Spacious Home 5 Mins To College & Frederick Health

Inns of Whitetail #209

10.0 out of 10, Exceptional, (1)
"Love the natural beauty all around."
The price is SAR 492
SAR 920 total
includes taxes & fees
9 Sep - 10 Sep
Inns of Whitetail #209

Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry

9.8 out of 10, Exceptional, (11)
"Small basement apartment had all we needed and wanted. Wonderful location. "
The price is SAR 426
SAR 704 total
includes taxes & fees
9 Sep - 10 Sep
Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry

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

10.0 out of 10, Exceptional, (4)
"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"
The price is SAR 284
SAR 1,125 total
includes taxes & fees
9 Sep - 10 Sep
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

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

9.4 out of 10, Exceptional, (103)
"Such a special home…cozy and filled with charm! Amazing views!"
The price is SAR 597
SAR 1,110 total
includes taxes & fees
10 Sep - 11 Sep
Historic cozy farmhouse in the ❤️ of Myersville , MD close to Rt 70! Welcome Home

*Luxury Condo In Downtown Frederick*

9.0 out of 10, Wonderful, (66)
"Wonderful space, perfect for our family, accurate description and depiction. "
The price is SAR 600
SAR 1,221 total
includes taxes & fees
22 Sep - 23 Sep
*Luxury Condo In Downtown Frederick*

1939 4BR Rustic Escape by Casino, 1939 4BR Rustic Escape by Casino

10.0 out of 10, Exceptional, (2)
"Convenient location, close to casino & river tubing. The house was cozy & comfortable for all of us. "
1939 4BR Rustic Escape by Casino, 1939 4BR Rustic Escape by Casino

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

10.0 out of 10, Exceptional, (2)
"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. "
The price is SAR 938
SAR 1,571 total
includes taxes & fees
14 Sep - 15 Sep
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC

Harpers Ferry Luxury, Spa Bathroom, Movie Room, high-end design and furnishings

9.8 out of 10, Exceptional, (23)
"We visited Harper’s Ferry just for a few days and Paul’s place was perfect for that. It was clean, comfortable, close to town, and close to trails. We had a wonderful time! Paul was very responsive and told us everything we needed to know. "
Harpers Ferry Luxury, Spa Bathroom, Movie Room, high-end design and furnishings

Newly renovated - Walk to Harpers Ferry NP

10.0 out of 10, Exceptional, (1)
"The place was just as described. In walking distance to Harper’s Ferry, and a short drive to the wineries in the area. The host was very responsive and accommodating."
The price is SAR 432
SAR 837 total
includes taxes & fees
9 Sep - 10 Sep
Newly renovated - Walk to Harpers Ferry NP

Modern Suite with Private Bath – Stylish & Comfy

The price is SAR 525
SAR 636 total
includes taxes & fees
20 Sep - 21 Sep
Modern Suite with Private Bath – Stylish & Comfy
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