Holiday Homes in Shepherdstown

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Featured Holiday Homes in Shepherdstown and around

Exclusive Wooded Chalet w Magnificent River Views

10.0 out of 10, Exceptional, (5)
"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. "
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, (128)
"The property is wonderful! Very cozy and convenient to local attractions."
The price is €300
includes taxes & fees
6 Sept - 7 Sept
Charming "Cream of the Crop" Cape ~❤️of Middletown

Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry

2.0 star property
9.8 out of 10, Exceptional, (8)
"Great place and good location."
The price is €270
includes taxes & fees
28 Aug - 29 Aug
Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry

Inns of Whitetail #209

10.0 out of 10, Exceptional, (1)
"Love the natural beauty all around."
The price is €214
includes taxes & fees
25 Aug - 26 Aug
Inns of Whitetail #209

Chic, pets, walk to downtown

10.0 out of 10, Exceptional, (13)
"Beautiful home with all desired ammenaties and very professional owners"
Chic, pets, walk to downtown

Downtown Charm: Pets Welcome

10.0 out of 10, Exceptional, (1)
"House was nice and cozy. And short trip to downtown area. Would definately stay here again."
Downtown Charm: Pets Welcome

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

9.4 out of 10, Exceptional, (102)
"Very nice old farm house with modern conveniences.. Comfortable and quiet. The antiques brought back memories of me visiting my grandparents back in the day. "
The price is €257
includes taxes & fees
4 Sept - 5 Sept
Historic cozy farmhouse in the ❤️ of Myersville , MD close to Rt 70! Welcome Home

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

9.4 out of 10, Exceptional, (114)
"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 €251
includes taxes & fees
7 Sept - 8 Sept
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

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 €346
includes taxes & fees
8 Sept - 9 Sept
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

Kalia’s Mountain Momma Getaway

10.0 out of 10, Exceptional, (11)
"Location was nice"
The price is €155
includes taxes & fees
25 Aug - 26 Aug
Kalia’s Mountain Momma Getaway

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!!"
Lakefront House w/ Modern Comforts!

Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry

9.6 out of 10, Exceptional, (8)
"Small basement apartment had all we needed and wanted. Wonderful location. "
The price is €165
includes taxes & fees
2 Sept - 3 Sept
Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry

The Boston - Family Escape

10.0 out of 10, Exceptional, (2)
"Very comfortable beds, everything we needed in a house. Beautifully furnished. The piano and table tennis were a fun addition."
The Boston - Family Escape

*Luxury Condo In Downtown Frederick*

9.0 out of 10, Wonderful, (66)
"The home was exactly as expected and made for a wonderful family/friend reunion! Perfect for socializing and so close to local shops and restaurants."
*Luxury Condo In Downtown Frederick*

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 €391
includes taxes & fees
6 Sept - 7 Sept
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC

Modern, family-friendly, nature packed getaway

9.0 out of 10, Wonderful, (17)
"we lived three nights and enjoyed the family retreat. "
Modern, family-friendly, nature packed getaway

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

Modern Cabin w Hot Tub & Indoor Pool/Gym Access!

8.6 out of 10, Excellent, (10)
"Great location, everything was great and we would stay again!"
Modern Cabin w Hot Tub & Indoor Pool/Gym Access!

Camp Patowmack - Riverfront, Hot Tub, and Sauna!

10.0 out of 10, Exceptional, (2)
"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 €465
includes taxes & fees
1 Sept - 2 Sept
Camp Patowmack - Riverfront, Hot Tub, and Sauna!
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