Holiday Rentals in Shepherdstown

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Holiday Rentals in Shepherdstown

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! "
The price is €445
includes taxes & fees
27 Jul - 28 Jul
Exclusive Wooded Chalet w Magnificent River Views

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

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

10.0 out of 10, Exceptional, (51)
"What a charming place to stay in Jefferson. The Rust Rose had everything we needed in a nice location. We would definitely stay here again."
The price is €218
includes taxes & fees
29 Jul - 30 Jul
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

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

9.4 out of 10, Exceptional, (109)
"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 €231
includes taxes & fees
29 Jul - 30 Jul
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

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 €268
includes taxes & fees
24 Jul - 25 Jul
Chic, pets, walk to downtown

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

10.0 out of 10, Exceptional, (33)
"It is a cute house out in the country. Loved being away from town just like our home"
Wine Weekend Getaway: Steps to Winery & Battlefield w/ Mountain Views & Hot Tub!

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

9.4 out of 10, Exceptional, (101)
"The house is very cool and great effort was put into the decor and arrangement. Very comfortable beds and everything you need is there. great communication!"
The price is €249
includes taxes & fees
24 Jul - 25 Jul
Historic cozy farmhouse in the ❤️ of Myersville , MD close to Rt 70! Welcome Home

Inns of Whitetail #209

10.0 out of 10, Exceptional, (1)
"Love the natural beauty all around."
The price is €216
includes taxes & fees
23 Jul - 24 Jul
Inns of Whitetail #209

Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry

2.0 star property
10.0 out of 10, Exceptional, (4)
"Great place and good location."
Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry

Lakefront House w/ Modern Comforts!

9.0 out of 10, Wonderful, (2)
"The house is lovely. Very much enjoyed the stay. Looking forward to going back!!"
Lakefront House w/ Modern Comforts!

*Luxury Condo In Downtown Frederick*

9.0 out of 10, Wonderful, (64)
"Clean & plenty of room. "
*Luxury Condo In Downtown Frederick*

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

10.0 out of 10, Exceptional, (123)
"The property is wonderful! Very cozy and convenient to local attractions."
The price is €272
includes taxes & fees
12 Aug - 13 Aug
Charming "Cream of the Crop" Cape ~❤️of Middletown

Kalia’s Mountain Momma Getaway

10.0 out of 10, Exceptional, (8)
"Location was nice"
The price is €156
includes taxes & fees
23 Jul - 24 Jul
Kalia’s Mountain Momma Getaway

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

10.0 out of 10, Exceptional, (1)
The price is €250
includes taxes & fees
23 Jul - 24 Jul
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

Enchanting Cottage, walk to Downtown Harpers Ferry

9.8 out of 10, Exceptional, (39)
"This place was perfect for our one-night stay in Harpers Ferry. Its location is in easy walking distance of the main sites. The house is old but charming. "
Enchanting Cottage, walk to Downtown Harpers Ferry

3-bedroom townhome in charming Hagerstown with AC, WiFi

The price is €207
includes taxes & fees
21 Aug - 22 Aug
3-bedroom townhome in charming Hagerstown with AC, WiFi

Terra Alta - Incredible River Views and Hot Tub!

9.8 out of 10, Exceptional, (57)
"We had a great time! The house overlooks the river and we loved the hot tub and fire pit! "
The price is €355
includes taxes & fees
31 Jul - 1 Aug
Terra Alta - Incredible River Views and Hot Tub!

Family Cottage - 6 Mins to River, Hiking & Wineries

10.0 out of 10, Exceptional, (9)
"This property had everything we could ever need. It was beautiful, clean and totally up to date. I highly recommend this house for your visit!"
The price is €330
includes taxes & fees
23 Jul - 24 Jul
Family Cottage - 6 Mins to River, Hiking & Wineries

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

10.0 out of 10, Exceptional, (1)
"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 €425
includes taxes & fees
29 Jul - 30 Jul
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC

Hot Tub, Campfire Ring, Convenient Location, Large Groups!!

9.6 out of 10, Exceptional, (94)
"Great find for a girls trip…house is close to lots of different activities and very easy to get to. Perfect place to a weekend getaway!"
The price is €397
includes taxes & fees
13 Aug - 14 Aug
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
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

Frequently asked questions

Are there holiday rentals in Shepherdstown?

Yes, there are holiday rentals close to the most popular sights in Shepherdstown, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the riverfront in Shepherdstown. Make sure you have time to check out the university setting and gardens during your trip.

What are some of the best holiday rentals that Shepherdstown has to offer?

Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!: This holiday home rental outside of Shepherdstown is located on a river, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of private gardens in this rental home to help you unwind.

How many holiday rentals will I find in Shepherdstown?

Expedia has 8 holiday rentals for your stay in Shepherdstown.

What’s there to see and do in Shepherdstown?

Cultural attractions include Shepherdstown Opera House and Shepherdstown Museum, whereas Morgan's Grove Park is one spot to enjoy nature. While here, Shepherdstown Visitors Center and Rumsey Steamboat Museum are other places worth a visit.

What’s a holiday rental in Shepherdstown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Shepherdstown. Holiday rentals feature extras such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a clean environment, holiday rentals can provide a sense of security away from shared hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for a family trip or a small group gathering.