Shepherdstown Vacation Rentals

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Vacation 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 $75
$144 total
includes taxes & fees
Jun 23 - Jun 24
❤️ 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 $94
$216 total
includes taxes & fees
Jul 1 - Jul 2
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
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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, 34 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 $155
$297 total
includes taxes & fees
Jun 17 - Jun 18
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
"Great place to relax ans recharge. Some much wildlife to see and quiet retreat close to hiking, etc. Will stay again"
The price is $145
$330 total
includes taxes & fees
Jun 19 - Jun 20
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 $122
$296 total
includes taxes & fees
Jun 18 - Jun 19
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, 63 reviews
"Went to some of the civil war sights and sight seeing hiked a few trails cabin is right near anything you could want for restaurants and shops but is far enough way from towns so it is very quiet at night spent every evening on the back porch enjoying the peace love the history of the cabin as well"
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, 97 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
"Nice location for visiting Harpers Ferry. Great porch for watching the sunrise if you're up early."
The price is $145
$223 total
includes taxes & fees
Jul 1 - Jul 2
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 $180
$350 total
includes taxes & fees
Jul 7 - Jul 8
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
"Had a great time at this property and were able to take advantage of the screened in porch and fireplace. Neighborhood was very nice and checkin was easy. They were very accommodating for the three dogs that also visited the property with us."
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 $170
$426 total
includes taxes & fees
Jun 20 - Jun 21
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, 93 reviews
"We enjoyed our stay at this historic home in the middle of town. We loved sitting on the porch and we slept great both nights."
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."
The price is $198
$491 total
includes taxes & fees
Jun 27 - Jun 28
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 $75
$144 total
includes taxes & fees
Jun 23 - Jun 24
❤️ Secluded 1940s Romantic Tiny House on the River
Country Inn & Suites by Radisson, Frederick, MD
Room, 2 Queen Beds, Non Smoking | Premium bedding, down comforters, pillowtop beds, in-room safe
Country Inn & Suites by Radisson, Frederick, MD
3.0 star property
8.6 out of 10, Excellent, 1,008 reviews
"Great place for a quick stop-over. I'm not sure I would stay for an extended period, but it was a pleasant, clean, friendly place for the night we stayed there. Located near lots of shopping. Safe, clean environment."
The price is $81
$90 total
includes taxes & fees
Jun 23 - Jun 24
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, 1,006 reviews
"Awesome stay."
The price is $101
$112 total
includes taxes & fees
Jul 7 - Jul 8
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Shepherdstown vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Shepherdstown vacation 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 low season months. For more hustle and bustle, you may prefer to visit Shepherdstown in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $75 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Shepherdstown rentals

At Expedia, we put the best Shepherdstown vacation 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 vacation.

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 vacation rentals in Shepherdstown?

Yes, we have vacation rentals near well known local attractions in Shepherdstown, or you can go with a more secluded option if you want a relaxing place to 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's the top vacation rental in Shepherdstown?

Welcome to this patch of serenity on the river's edge, to this hideaway.: Visitors give good reviews to this Shepherdstown vacation home rental, which is located on a river and has a balcony, a garden, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals will I find in Shepherdstown?

Expedia has 9 vacation 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 vacation rental in Shepherdstown like?

Vacation rentals are private properties you can stay in for a couple of days or more in Shepherdstown. Vacation rentals feature amenities like kitchens and laundry facilities so you'll have everything you want. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from shared hotel elevators and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for a small group gathering.

Recent reviews of Shepherdstown properties
Expedia verified reviews

Hampton Inn Hagerstown

Hampton Inn Hagerstown

5/5 Excellent
"this property was clean and comfortable. Staff was Welcoming and very attentive. I asked for an extra towel and they brought it to our room within minutes. our room was very comfortable. The only suggestion I have would be to fix the showerhead so that the water dispenses through the entire showerhead rather than the perimeter. Otherwise, a great property!"
A verified traveler stayed at Hampton Inn Hagerstown
Posted 2 days ago
Hampton Inn Hagerstown