Shepherdstown Holiday Rentals

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Holiday Rentals in Shepherdstown

❤️ Secluded 1940s Romantic Tiny House on the River

10.0 out of 10, Exceptional, (47)
"My husband and I stayed here to celebrate our second anniversary. We wanted just a quiet getaway and it was the perfect place. Definitely will have to come back again."
The price is AU$172
includes taxes & fees
3 Dec - 4 Dec
❤️ 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, (23)
"Quiet and relaxing. Had hoped to get the kayaks out but one girl was just post surgery on her wrist so we had to bypass them this trip. Our favorite part of the weekend was sitting on the porch and looking at the Potomac. So relaxing. The house was cute and clean, just like the pictures. Shopped in Shepersdstown and ate at the Blur Moon. It was fun!! Could not find parking in Harper’s Ferry. We were bummed about that but it didn’t ruin our weekend. We will be back to kayak and swim. "
Plum Lazy on the Potomac

Hidden Gem in the woods with hot tub

9.4 out of 10, Exceptional, (63)
"Great location, a little out of the way, but very relaxing. Great hot tub and fire pit. My family and I had an amazing time. "
Hidden Gem in the woods with hot tub

Countryside Cabin with Mountain Views near Surreybrooke Gardens

10.0 out of 10, Exceptional, (85)
"My husband and I were beyond thrilled with this property. Absolutely incredible and are looking forward to visiting again!"
Countryside Cabin with Mountain Views near Surreybrooke Gardens

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!

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

9.8 out of 10, Exceptional, (86)
"We were looking to unplug for a night, and this cottage was the perfect spot! Clean and well kept, calm and quiet surroundings. One note is that the WiFi was not working. We didn’t need it for our trip, but something to keep in mind!"
The price is AU$346
includes taxes & fees
24 Nov - 25 Nov
Riverside cottage, minutes from historic Harpers Ferry! Private river access!

Cozy Mountain Cabin w/ Steam Shower. Family Friendly!

10.0 out of 10, Exceptional, (51)
"Comfy cabin with everything topline. Loved the sunroom and the steam shower. Daily watching deer feed and stroll through the yard below. Gus wasn’t happy about it but he still watched through floor to ceiling windows."
The price is AU$467
includes taxes & fees
5 Dec - 6 Dec
Cozy Mountain Cabin w/ Steam Shower. Family Friendly!

The Oculus - Huge Cabin with a Hot Tub!

9.8 out of 10, Exceptional, (15)
"Rustic."
The Oculus - Huge Cabin with a Hot Tub!

Best location! The Pullman Apt @ historic 1799 Inn

9.4 out of 10, Exceptional, (25)
"When I booked this stay, I didn’t realize how much history we would be surrounded by! Museums, shops and great restaurants within walking distance. Plenty of hiking all around with access to the Appalachian trail. Access to e-bikes. Breweries and groceries just a short drive away"
The price is AU$295
includes taxes & fees
24 Nov - 25 Nov
Best location! The Pullman Apt @ historic 1799 Inn

Antietam Creek - Quiet 2 Bedroom Cabin

9.4 out of 10, Exceptional, (76)
"We were visiting with family in Boonsboro and arrived late in the evening and left by 9am, but everything was there that we would have needed for a longer stay, which we have planned for Thanksgiving. Kitchen was very well equipped, the space was inviting, the beds were comfy and the view out the back was great, Looking forward to our return!"
The price is AU$517
includes taxes & fees
24 Nov - 25 Nov
Antietam Creek - Quiet 2 Bedroom Cabin

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

9.8 out of 10, Exceptional, (46)
"The location is not convenient for access, and the master bedroom cannot take a shower"
The price is AU$584
includes taxes & fees
12 Dec - 13 Dec
Hot Tub, Deck/Grill, Game Room, WiFi at Cute Cabin

Antietam Toll House~ an historic waterfront cabin

9.8 out of 10, Exceptional, (68)
"Well maintained property; loved the fenced yards for my dog and our walks along the creek. "
The price is AU$439
includes taxes & fees
24 Nov - 25 Nov
Antietam Toll House~ an historic waterfront cabin

Woodpecker Woods - Cozy Log Cabin w/ Hot Tub!

9.8 out of 10, Exceptional, (19)
"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...
Woodpecker Woods - Cozy Log Cabin w/ Hot Tub!

Waterfront Cabin overlooking the Potomac River W/ Hot Tub

9.8 out of 10, Exceptional, (48)
"Super pleased with everything. Enjoyed our stay so. Very much. Would love to come back sometime. "
The price is AU$455
includes taxes & fees
1 Dec - 2 Dec
Waterfront Cabin overlooking the Potomac River W/ Hot Tub

Rustic Log Cabin with Private Dock on the Lake!

9.8 out of 10, Exceptional, (11)
"Amazing location!!! 18 minutes from a cluster of wineries; quiet and relaxing. Definitely will be visiting again "
Rustic Log Cabin with Private Dock on the Lake!

RIVERKEEPER INN, Waterfront Property on the Potomac River

9.4 out of 10, Exceptional, (113)
"Enjoyed sitting on the deck above the river in the evenings, quiet and peaceful looking forward to staying there again."
RIVERKEEPER INN, Waterfront Property on the Potomac River

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

9.8 out of 10, Exceptional, (216)
"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

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

9.8 out of 10, Exceptional, (50)
"The place was adorable. The view was amazing!"
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!

Waterfront property in Harpers Ferry - Private River Access

10.0 out of 10, Exceptional, (21)
"Our stay at this vacation home was very enjoyable! The house was clean, well maintained and comfortable. It is located on a nice piece of property with a beautiful view of the Shenandoah River. The owner provided a lot of necessities like bed sheets, bath towels, soap, shampoo and even coffee supplies. The house is up to date and has a nice basement entertainment area. The fire pit area near the river was probably our favorite amenity. We enjoyed it on a couple evenings while enjoying the...
Waterfront property in Harpers Ferry - Private River 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.
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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, (47)
"My husband and I stayed here to celebrate our second anniversary. We wanted just a quiet getaway and it was the perfect place. Definitely will have to come back again."
The price is AU$172
includes taxes & fees
3 Dec - 4 Dec
❤️ 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, (1017)
"Nice place and a value at the price point. Gracious staff and convenient location. "
The price is AU$128
includes taxes & fees
22 Dec - 23 Dec
Country Inn & Suites by Radisson, Frederick, MD

Country Inn & Suites by Radisson, Hagerstown, MD

3.0 star property
8.6 out of 10, Excellent, (1062)
"Convenient for dining and shopping "
The price is AU$167
includes taxes & fees
8 Dec - 9 Dec
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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 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.