Shepherdstown Holiday Rentals

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Shepherdstown

❤️ Secluded 1940s Romantic Tiny House on the River

10.0 out of 10, Exceptional, (49)
"Excellent little cabin right on the river and close to DT Sheperdstown which is a great town."
The price is AU$180
includes taxes & fees
13 Jan - 14 Jan
❤️ Secluded 1940s Romantic Tiny House on the River

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

9.8 out of 10, Exceptional, (60)
"Loved everything. Quiet, peaceful….loved the small deck off the upstairs bedroom."
Welcome to this patch of serenity on the river's edge, to this hideaway.

Plum Lazy on the Potomac

9.2 out of 10, Wonderful, (24)
"Everything was as advertised! We really enjoyed our stay and can't wait to return!"
Plum Lazy on the Potomac

Waterfront Cabin overlooking the Potomac River W/ Hot Tub

9.8 out of 10, Exceptional, (49)
"Super pleased with everything. Enjoyed our stay so. Very much. Would love to come back sometime. "
The price is AU$445
includes taxes & fees
8 Jan - 9 Jan
Waterfront Cabin overlooking the Potomac River W/ Hot Tub

Hidden Gem in the woods with hot tub

9.6 out of 10, Exceptional, (67)
"Nice"
Hidden Gem in the woods with hot tub

Riverside cottage, minutes from historic Harpers Ferry! Private river access!

9.6 out of 10, Exceptional, (89)
"Great year round location. Owners are nearby if issues occur. HIGHLY RECOMMENDED. "
Riverside cottage, minutes from historic Harpers Ferry! Private river access!

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

10.0 out of 10, Exceptional, (46)
"House was very comfortable for our family. The kids loved the flexibility of the sleeping arrangements. "
Luxurious Mountaintop Chalet / Cabin in 'The Woods Golf Resort':Access Amenities

Woodpecker Woods - Cozy Log Cabin w/ Hot Tub!

9.8 out of 10, Exceptional, (20)
"My friends and I always choose a new cabin for our annual fall getaway. We've not had a bad experience yet. Mountain Mama's Woodpecker Woods did not disappoint, either! Comfortable, warm, clean, spacious log cabin. It had everything we needed. In fact, it was so relaxing, we never made it to the hot tub. We did visit Harper's Ferry Park and enjoyed walking the hiking trail to the downtown area. :-) We especially loved the close proximity to the Washington, DC Metro area. If there was anything...
The price is AU$573
includes taxes & fees
13 Jan - 14 Jan
Woodpecker Woods - Cozy Log Cabin w/ Hot Tub!

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

10.0 out of 10, Exceptional, (110)
"This property could not have been more quaint and peaceful. My husband, two dogs and I enjoyed the long weekend, walking the trails and taking in the history of Harper’s Ferry. I would highly recommend this property to anyone looking for a quiet getaway. The location could not be better for seeing the town on foot. The property was clean and so neatly appointed. Breathtaking views! "
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!

Beautiful Cottage At 'the Woods' Resort, Golf, Spa, Swimming & Resort Amenities

9.8 out of 10, Exceptional, (219)
"Myself and two friends went for a two night stay and it couldn't have been better. The hosts were reasonable, practical with all their expectations and they were very responsive and kind during the planning stages and when we arrived. The house was well supplied with everything we needed. Unfortunately there was an outdoor burn ban in place due to drought, but the fire pit looked very comfortable and we even talked about coming back to enjoy it next year. We did light a fire inside and it was...
Beautiful Cottage At 'the Woods' Resort, Golf, Spa, Swimming & Resort Amenities

Terra Alta - Incredible River Views and Hot Tub!

9.8 out of 10, Exceptional, (52)
"Está bien hermosa la casa "
The price is AU$656
includes taxes & fees
9 Jan - 10 Jan
Terra Alta - Incredible River Views and Hot Tub!

Antietam Toll House~ an historic waterfront cabin

9.8 out of 10, Exceptional, (70)
"We just needed to get out of the city for a night and this was a perfect spot. Cute, comfortable, and with pretty much any amenity you could need. "
The price is AU$456
includes taxes & fees
7 Jan - 8 Jan
Antietam Toll House~ an historic waterfront cabin

Sunny Streams Cabin - Sunset Views w/ a Hot Tub!

9.8 out of 10, Exceptional, (51)
"The place was adorable. The view was amazing!"
The price is AU$722
includes taxes & fees
14 Jan - 15 Jan
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!

Walk to Potomac River and downtown Harpers Ferry

10.0 out of 10, Exceptional, (111)
"The house was amazing, great views and a great layout that allowed for us to hang as a group or have some privacy. Very convenient to everything we wanted to do; Harper’s Ferry, Ziplining (or rafting based on time of year), and the Brewery that we went to on the last night felt like it was almost walking distance. Definitely recommend and would stay again in a heartbeat. "
Walk to Potomac River and downtown Harpers Ferry

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

10.0 out of 10, Exceptional, (117)
"We were looking for a quiet getaway location from the Black Friday and Small Business Saturday crowds, but also a location that was close to several small towns near the area...and this property checked all boxes! Everywhere you go within 20-30 minutes is a delight for the history, art, music collector, foodie, entertainment, wine, distillery, brewery, or shopping fanatic...a delightful home and one we hope to visit again!"
The price is AU$398
includes taxes & fees
7 Jan - 8 Jan
Charming "Cream of the Crop" Cape ~❤️of Middletown

Secluded Cabin a Stone's Throw From the A.T.!

9.8 out of 10, Exceptional, (17)
"We were charmed by the house and pleased with all the amenities. We would definitely stay there again. "
The price is AU$773
includes taxes & fees
12 Jan - 13 Jan
Secluded Cabin a Stone's Throw From the A.T.!

Hot Tub, Deck/Grill, Game Room, WiFi at Cute Cabin

9.6 out of 10, Exceptional, (50)
"My husband and I along with our 2 small dogs had a wonderful stay at this lovely mountain retreat. The cabin was clean and comfortable and had everything that we needed to cook breakfast and an easy dinner each evening. The property was beautiful with lots of tall old growth trees that were beautiful with the fall colors and even though it was in a community you felt like you were in a secluded mountain retreat because most of the homes were obsured by the trees; and it is on a dead end road...
The price is AU$504
includes taxes & fees
13 Jan - 14 Jan
Hot Tub, Deck/Grill, Game Room, WiFi at Cute Cabin

Charles Town Home w/ Private Pool & Hot Tub

10.0 out of 10, Exceptional, (40)
"Lots of space for everyone, excellent pool and hot tub"
Charles Town Home w/ Private Pool & Hot Tub

Countryside Cabin with Mountain Views near Surreybrooke Gardens

10.0 out of 10, Exceptional, (88)
"Cozy cabin, wonderful hosts, great location near the AT. Probably the most thoughtful host we’ve had, they’ve thought of everything from breakfast treats and extra linens, even dog treats."
Countryside Cabin with Mountain Views near Surreybrooke Gardens

Berkeley Springs Haven w/ Sleepy Creek Access!

10.0 out of 10, Exceptional, (60)
"The cottage was perfect for our needs. The wifi listed online was not correct, however, the owner came over immediately to figure out the issue. One suggestion would be to supply mini toiletries (shampoo, conditioner, body wash, etc.) We enjoyed our quick visit!"
Berkeley Springs Haven w/ Sleepy Creek Access!
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.
Don't see what you're looking for?
See all available properties in Shepherdstown
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Shepherdstown you may be interested in

❤️ Secluded 1940s Romantic Tiny House on the River

10.0 out of 10, Exceptional, (49)
"Excellent little cabin right on the river and close to DT Sheperdstown which is a great town."
The price is AU$180
includes taxes & fees
13 Jan - 14 Jan
❤️ Secluded 1940s Romantic Tiny House on the River

Country Inn & Suites by Radisson, Frederick, MD

3.0 star property
8.4 out of 10, Very good, (1009)
"The staff the room and the overall experience "
The price is AU$146
includes taxes & fees
21 Jan - 22 Jan
Country Inn & Suites by Radisson, Frederick, MD

Country Inn & Suites by Radisson, Hagerstown, MD

3.0 star property
8.6 out of 10, Excellent, (1054)
"Quick Smooth check in and out. Comfortable beds Great shower"
The price is AU$161
includes taxes & fees
21 Jan - 22 Jan
Country Inn & Suites by Radisson, Hagerstown, MD
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.

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?

Welcome to this patch of serenity on the river's edge, to this hideaway.: This highly rated holiday home rental in Shepherdstown is located on a river, and has a balcony, a private garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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 Museum and Shepherdstown Opera House, whereas Morgan's Grove Park and Bane Harris Community Park are a couple of picturesque spots to enjoy the outdoors. 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.