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Top Holiday Rentals in Shepherdstown

❤️ Secluded 1940s Romantic Tiny House on the River

10.0 out of 10, Exceptional, (57)
"We truly loved this location and definitely will be back!"
The price is £109
includes taxes & fees
1 Sept - 2 Sept
❤️ Secluded 1940s Romantic Tiny House on the River

Welcome to this patch of serenity on the river's edge, to this hideaway.

10.0 out of 10, Exceptional, (63)
"Enjoyed our stay!!"
Welcome to this patch of serenity on the river's edge, to this hideaway.

RIVERKEEPER INN, Waterfront Property on the Potomac River

9.2 out of 10, Wonderful, (125)
"Riverkeeper Inn is located in a peaceful and quiet area of Harpers Ferry, equally perfect in early mornings and late nights. The check-in and check-out process were very easy, and the property itself had everything we could've asked for, and then some."
RIVERKEEPER INN, Waterfront Property on the Potomac River

Private, light filled retreat space... with your own pickleball court!

10.0 out of 10, Exceptional, (41)
"The pictures for this cabin don't reflect how roomy and spacious this place is! It is a very clean, comfortable and quiet retreat. My wife and I had a fantastic stay and would not hesitate to book this place again if we are in the area.Thanks Patty and Bill for allowing us to stay at this wonderful place."
Private, light filled retreat space... with your own pickleball court!

Charming Cabin in the Woods with River Access

9.8 out of 10, Exceptional, (29)
"Very nice rest time…"
Charming Cabin in the Woods with River Access

Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!

10.0 out of 10, Exceptional, (127)
"Spectacular location. Charming and comfortable. The steps can be a challenge but are worth the effort."
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!

Waterfront Cabin overlooking the Potomac River W/ Hot Tub, firepit, pavilion

9.8 out of 10, Exceptional, (66)
"This little cabin was absolutely wonderful. The nicest amenities and very clean. Had everything we needed for a short weekend getaway. I especially loved the hot tub and the indoor massage chair! We come to this area once a year-will definitely stay here again. "
The price is £224
includes taxes & fees
11 Aug - 12 Aug
Waterfront Cabin overlooking the Potomac River W/ Hot Tub, firepit, pavilion

Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry

9.6 out of 10, Exceptional, (7)
The price is £150
includes taxes & fees
11 Aug - 12 Aug
Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry

Quaint Loft Cabin w/Hot Tub, FirePit, Deck & Grill

8.4 out of 10, Very good, (10)
"We had a great time in West Virginia and the Chalet. The properry was well maintained and the host was very proactive with checking in to see if we arrived and got inside without incident, and to see if we needed anythjng. "
The price is £230
includes taxes & fees
17 Aug - 18 Aug
Quaint Loft Cabin w/Hot Tub, FirePit, Deck & Grill

Modern Country House on the Shenandoah River

9.8 out of 10, Exceptional, (36)
"The views are beautiful and the house was the perfect size for a group of 7 friends. We had a great time!"
Modern Country House on the Shenandoah River

Spacious w/Hot Tub, Fire Pit, Deck, Grill and WiFi

9.8 out of 10, Exceptional, (17)
"We had a great time exploring the region from Spleepy Hollow. The hot tub after a long hike is always great!"
The price is £190
includes taxes & fees
13 Aug - 14 Aug
Spacious w/Hot Tub, Fire Pit, Deck, Grill and WiFi

Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

9.8 out of 10, Exceptional, (98)
"This home was absolutely fantastic! Very clean, very close to all things. We had a fantastic time."
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

Hidden Gem in the woods with hot tub

9.6 out of 10, Exceptional, (80)
"Beautiful location and great little cabin "
Hidden Gem in the woods with hot tub

Amazing dog-friendly cottage. Walk 2 Harpers Ferry

2.0 star property
9.8 out of 10, Exceptional, (15)
"Very nice property with convenient location! Within walking distance of down town. "
The price is £250
includes taxes & fees
17 Aug - 18 Aug
Amazing dog-friendly cottage. Walk 2 Harpers Ferry

Luxurious Mountaintop Chalet / Cabin in 'The Woods Golf Resort':Access Amenities

10.0 out of 10, Exceptional, (63)
"Great home with many amenities and beautiful views "
Luxurious Mountaintop Chalet / Cabin in 'The Woods Golf Resort':Access Amenities

Lake House w/ Pool and King Bed, Fishing - Dogs OK

9.4 out of 10, Exceptional, (22)
"The lake house property was clean, comfortable and was an excellent location. We enjoyed the proximity to Gettysburg, Harper’s Ferry, Cacapon State Park and the C and O Towpath bike trail and museum."
Lake House w/ Pool and King Bed, Fishing - Dogs OK

Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.

10.0 out of 10, Exceptional, (138)
"Wonderful house for a great weekend away"
The price is £298
includes taxes & fees
8 Sept - 9 Sept
Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.

Historic Boonsboro Vacation Rental w/ Grill

9.2 out of 10, Wonderful, (16)
"It was perfect. Near my son’s school at Shepherd University and close to all the historic sites of Harper’s Ferry and Antietam."
Historic Boonsboro Vacation Rental w/ Grill

Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

9.6 out of 10, Exceptional, (99)
"Our weekend cabin stay was wonderful. The safe neighborhood was quite and peaceful. Its location near nature and the city was just perfect. The cozy cabin was clean and comfy. We loved Gambrill State Park and downtown Frederick didn't disappoint as well."
The price is £142
includes taxes & fees
14 Aug - 15 Aug
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

Luxury Getaway on The Potomac

9.6 out of 10, Exceptional, (15)
"We will be coming back to this hidden gem on the Potomac. The house is immaculate. Perfect spot for a family or a large group of friends. Even in early April, a few in our group used the docks to plunge in the river. Can’t wait to bring the family back. "
Luxury Getaway 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.
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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 Shepherdstown Public Library 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.