Shepherdstown Holiday Rentals

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Holiday Rentals in Shepherdstown

❤️ Secluded 1940s Romantic Tiny House on the River
Beach
❤️ Secluded 1940s Romantic Tiny House on the River
10.0 out of 10, Exceptional, 41 reviews
"The tiny house is exactly as described. Its small, clean, cozy and comfortable. The location right on the river is fantastic. Being able to have a fire right by the water each night was such a plus. In better weather would be a great put in for canoeing, kataking. Very close many historic sights, unique shops, and outdoor activities. The hosts are very thoughtful, kind and responsive. We will be staying again!!"
The price is AU$221
includes taxes & fees
30 June - 1 July
❤️ Secluded 1940s Romantic Tiny House on the River
Cozy Cottage
Exterior
Cozy Cottage
9.2 out of 10, Wonderful, 19 reviews
"Clean, quiet neighborhood, easy walk to downtown"
The price is AU$329
includes taxes & fees
1 July - 2 July
Cozy Cottage
Plum Lazy on the Potomac
Property grounds
Plum Lazy on the Potomac
9.4 out of 10, Exceptional, 20 reviews
"My friends and I loved this house can’t wait to go back."
Plum Lazy on the Potomac
Welcome to this patch of serenity on the river's edge, to this hideaway.
Fridge, microwave, oven, stovetop
Welcome to this patch of serenity on the river's edge, to this hideaway.
9.8 out of 10, Exceptional, 57 reviews
"We had a really lovely time at this space, Amy was such a good host, and we hope to return!"
Welcome to this patch of serenity on the river's edge, to this hideaway.
Hidden Gem in the woods with hot tub
Property grounds
Hidden Gem in the woods with hot tub
9.6 out of 10, Exceptional, 51 reviews
"We had a great time. Cabin was clean, spacious and well maintained. The fire pit and hot tub were what we looked forward to the most... We were not disappointed."
Hidden Gem in the woods with hot tub
Antietam Toll House~ an historic waterfront cabin
Property grounds
Antietam Toll House~ an historic waterfront cabin
9.8 out of 10, Exceptional, 53 reviews
"Very nice property along side of the Antietam Creek. Wonderful rustic charm with modern conveniences. Brilliantly located between Hagerstown MD and Gettysburg PA— good jumping off point for antiques or history."
Antietam Toll House~ an historic waterfront cabin
Waterfront Cabin overlooking the Potomac River W/ Hot Tub
Fridge, microwave, oven, stovetop
Waterfront Cabin overlooking the Potomac River W/ Hot Tub
9.8 out of 10, Exceptional, 35 reviews
"We had a wonderful time and rarely left the property! We stayed during the week so the campground was quiet. The cabin is very comfortable with everything you could possibly need. The decks overlooking the river were a favorite spot for coffee in the mornings and drinks in the evenings. Although we did not get into the hot tub, it did look lovely. Our water time was spent in the river where we saw deer, a hawk diving and catching his dinner, fish jumping and even a beaver! We love the cabin and...
The price is AU$456
includes taxes & fees
30 June - 1 July
Waterfront Cabin overlooking the Potomac River W/ Hot Tub
Cozy Mountain Cabin w/ Steam Shower. Family Friendly!
Smart TV, DVD player, books, video library
Cozy Mountain Cabin w/ Steam Shower. Family Friendly!
10.0 out of 10, Exceptional, 30 reviews
"Very clean. Crisp, clean linens. Gorgeous views and surroundings. Extremely responsive. Highly recommend!!"
The price is AU$505
includes taxes & fees
10 July - 11 July
Cozy Mountain Cabin w/ Steam Shower. Family Friendly!
Cabin w Hot Tub, Indoor Pool / Gym Access, & Grill
TV, fireplace, books, stereo
Cabin w Hot Tub, Indoor Pool / Gym Access, & Grill
9.4 out of 10, Exceptional, 9 reviews
"I would consider changing carpet to vinyl flooring. Good location if you love to golf."
The price is AU$448
includes taxes & fees
25 June - 26 June
Cabin w Hot Tub, Indoor Pool / Gym Access, & Grill
Countryside Cabin with Mountain Views near Surreybrooke Gardens
Exterior
Countryside Cabin with Mountain Views near Surreybrooke Gardens
10.0 out of 10, Exceptional, 64 reviews
"Property was beautifully manicured. Cabin was rustic but comfortable with all the comforts of home. I loved sitting on the huge wrap around porch in the morning listening to the birds and watching the sunrise."
Countryside Cabin with Mountain Views near Surreybrooke Gardens
Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.
Exterior
Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.
9.8 out of 10, Exceptional, 99 reviews
"The house was spotless was walking distance to everything we wanted to do. Would definitely coming back here to stay!"
Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.
Riverside cottage, minutes from historic Harpers Ferry; private river access!
Property grounds
Riverside cottage, minutes from historic Harpers Ferry; private river access!
9.8 out of 10, Exceptional, 60 reviews
"We enjoyed our stay! The location was perfect for us and the house worked well for young kids. Thank you!"
The price is AU$340
includes taxes & fees
1 July - 2 July
Riverside cottage, minutes from historic Harpers Ferry; private river access!
RIVERKEEPER INN, Waterfront Property on the Potomac River
View from property
RIVERKEEPER INN, Waterfront Property on the Potomac River
9.4 out of 10, Exceptional, 104 reviews
"We had a wonderful time, even in the rain! Easy river access and beautiful views of both the water and green spaces."
RIVERKEEPER INN, Waterfront Property on the Potomac River
Charming "Cream of the Crop" Cape ~❤️of Middletown
Property grounds
Charming "Cream of the Crop" Cape ~❤️of Middletown
10.0 out of 10, Exceptional, 102 reviews
"Cute cottage was clean and comfy. Everything you need to make a nice dinner, relax and enjoy the quiet neighborhood."
The price is AU$538
includes taxes & fees
7 July - 8 July
Charming "Cream of the Crop" Cape ~❤️of Middletown
Beautiful Cottage At 'the Woods' Resort, Golf, Spa, Swimming & Resort Amenities
Interior detail
Beautiful Cottage At 'the Woods' Resort, Golf, Spa, Swimming & Resort Amenities
9.8 out of 10, Exceptional, 208 reviews
"Beautiful cabin in a peaceful area. Just what we wanted"
Beautiful Cottage At 'the Woods' Resort, Golf, Spa, Swimming & Resort Amenities
Woodpecker Woods - Cozy Log Cabin w/ Hot Tub!
Property grounds
Woodpecker Woods - Cozy Log Cabin w/ Hot Tub!
9.6 out of 10, Exceptional, 10 reviews
"We enjoyed the cabin very much. We hiked during the day and was very relaxing coming back to the hot tub and a fire. Thank you for a great stay!!"
The price is AU$594
includes taxes & fees
20 June - 21 June
Woodpecker Woods - Cozy Log Cabin w/ Hot Tub!
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
Exterior
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
10.0 out of 10, Exceptional, 94 reviews
"The house was an excellent place for my family to stay during our visit to Harper's Ferry. It is conveniently located in downtown Harper's Ferry, and we enjoyed our visit."
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
Couples Cabin - 5 Mi to DT Berkeley Springs!
1 bedroom, Internet, bed sheets
Couples Cabin - 5 Mi to DT Berkeley Springs!
10.0 out of 10, Exceptional, 57 reviews
"Our stay was outstanding. The accommodations were perfect for a weekend couple get-away in the woods. Our unit was clean and very well furnished and decorated. The surrounding property was spectacular. We had the pleasure to meet the really nice hosts, and even got to tour the other rentals on the property. We will definitely be returning in a future visit to Berkely Springs. Fun little town. Take a hot mineral bath at the Spa just like George Washington."
Couples Cabin - 5 Mi to DT Berkeley Springs!
A newly renovated, pet-friendly Penthouse condo with private rooftop deck.
Interior
A newly renovated, pet-friendly Penthouse condo with private rooftop deck.
9.8 out of 10, Exceptional, 18 reviews
"Check-in was a breeze, the condo was very clean, and within walking distance to lots of restaurants and shops. My favorite perk of this place was the deck. It was perfect for enjoying coffee and wine! We will definitely be back!"
A newly renovated, pet-friendly Penthouse condo with private rooftop deck.
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
Interior
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
9.8 out of 10, Exceptional, 40 reviews
"Thoroughly enjoyed our stay at this property. The view was stunning and the communication and ease of check in was wonderful. We enjoyed the extra recommendations for wineries to visit and a weekend concert in Harper's Ferry. Very personalized and attentive service."
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
Don't see what you're looking for?
See all available properties in Shepherdstown
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.

Other types of properties in Shepherdstown you may be interested in

❤️ Secluded 1940s Romantic Tiny House on the River
Beach
❤️ Secluded 1940s Romantic Tiny House on the River
10.0 out of 10, Exceptional, 41 reviews
"The tiny house is exactly as described. Its small, clean, cozy and comfortable. The location right on the river is fantastic. Being able to have a fire right by the water each night was such a plus. In better weather would be a great put in for canoeing, kataking. Very close many historic sights, unique shops, and outdoor activities. The hosts are very thoughtful, kind and responsive. We will be staying again!!"
The price is AU$221
includes taxes & fees
30 June - 1 July
❤️ Secluded 1940s Romantic Tiny House on the River
Country Inn & Suites by Radisson, Frederick, MD
Room, 2 Queen Beds, Non Smoking
Country Inn & Suites by Radisson, Frederick, MD
3.0 star property
8.6 out of 10, Excellent, 1,000 reviews
"Staff was great. Room was great. When you pull up to the property it could use a little facelift but once inside it was nice. Very happy for the price I paid. "
The price is AU$133
includes taxes & fees
23 June - 24 June
Country Inn & Suites by Radisson, Frederick, MD
Hilton Garden Inn Frederick
Exterior
Hilton Garden Inn Frederick
3.0 star property
9.0 out of 10, Wonderful, 1,001 reviews
"Bathroom fan was very loud, and it couldn’t be turned off. Otherwise, great!"
The price is AU$170
includes taxes & fees
7 July - 8 July
Hilton Garden Inn Frederick
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.

Everything you need to know about Shepherdstown holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Shepherdstown holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Shepherdstown holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Shepherdstown holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Shepherdstown. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Shepherdstown holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Shepherdstown holiday rentals we have selected for you start as low as AU$221 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Shepherdstown rentals

At Expedia, we put the best Shepherdstown holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Shepherdstown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Shepherdstown holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Shepherdstown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 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 9 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.

Recent reviews of Shepherdstown properties
Expedia verified reviews

Clarion Inn Harpers Ferry - Charles Town

Clarion Inn Harpers Ferry - Charles Town

5/5 Excellent
"All the areas were spacious, the hallways, the lobby, the rooms, and especially the breakfast room! Super close to the entrance of the Harpers Ferry National Park. "
A verified traveller stayed at Clarion Inn Harpers Ferry - Charles Town
Posted 21 hours ago
Clarion Inn Harpers Ferry - Charles Town