Shepherdstown Holiday Rentals

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Our top choices for Shepherdstown holiday rentals

9.8 out of 10, Exceptional, (71 reviews)
"This trip was to celebrate my 64th birthday and wind down from my busy job It was perfect for both .. very relaxing, and very cozy. We'd love to stay again."
United States
Kaleb C
The price is AU$150
includes taxes & fees
9 Mar - 10 Mar
❤️ Secluded 1940s Romantic Tiny House on the River
10.0 out of 10, Exceptional, (16 reviews)
"This property was super nice and the property managers were super awesome and accommodating! "
United States
Construction V.
The price is AU$651
includes taxes & fees
3 Mar - 4 Mar
Exclusive Wooded Chalet w Magnificent River Views

Apartment in Frederick

Pet-friendly, heart of downtown
10.0 out of 10, Exceptional, (8 reviews)
"Very convenient to everything. Quick walk to shops, breweries, and restaurants."
United States
JENNIFER
The price is AU$259
includes taxes & fees
3 Mar - 4 Mar
Pet-friendly, heart of downtown
9.6 out of 10, Exceptional, (111 reviews)
"I’ve stayed here and will absolutely stay again."
United States
Katherine M.
The price is AU$249
includes taxes & fees
5 Mar - 6 Mar
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
10.0 out of 10, Exceptional, (21 reviews)
"Beautiful location. Just what we were looking for."
United States
tony l.
The price is AU$217
includes taxes & fees
3 Mar - 4 Mar
Birch Cabin at Hunting Creek Hideaway

Apartment in Frederick

Cozy, dog-friendly, downtown
10.0 out of 10, Exceptional, (28 reviews)
"Clean, great location, friendly owner"
United States
Christian M.
The price is AU$270
includes taxes & fees
3 Mar - 4 Mar
Cozy, dog-friendly, downtown
10.0 out of 10, Exceptional, (64 reviews)
"We had a great time. House was very comfortable and location was perfect."
United States
Liz R.
The price is AU$366
includes taxes & fees
3 Mar - 4 Mar
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
9.8 out of 10, Exceptional, (67 reviews)
"Great stay! We would book again. "
United States
Sam F.
The price is AU$520
includes taxes & fees
5 Mar - 6 Mar
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
9.8 out of 10, Exceptional, (34 reviews)
"The cabin was very easy to get to, and yet it felt like you were in the middle of nowhere. The view was excellent. The accommodations were top-notch. I recommend this place to anyone."
United States
Greg R.
The price is AU$504
includes taxes & fees
5 Mar - 6 Mar
Antietam Look Out - Incredible Sunset Views!

Holiday Home in Downtown Frederick

*Luxury Condo In Downtown Frederick*
9.0 out of 10, Wonderful, (77 reviews)
"Lovely place. It was perfect for our girls' trip long weekend. The rooms were so spacious and tastefully decorated. It was also super clean and had everything we needed, including for our night staying in with Door-dash to binge watch a couple Netflix series. The coffee lover in our group was so appreciative of the supplies and setup. The location is fabulous for walking the Creek Park, or to dinning and shopping options. We're looking forward to making this our Christmas present to each other...
United States
Lynne
The price is AU$367
includes taxes & fees
3 Mar - 4 Mar
*Luxury Condo In Downtown Frederick*
10.0 out of 10, Exceptional, (9 reviews)
"Our stay was amazing and we really enjoyed ourselves. The place was perfect and quiet and peaceful! We will be booking with them again! "
United States
Kyndal B.
The price is AU$229
includes taxes & fees
4 Mar - 5 Mar
Bring Your Own Boat - Meticulously restored house on the Potomac River
10.0 out of 10, Exceptional, (7 reviews)
"Host was very responsive before and during my stay. Apartment is beautifully appointed and has all the amenities you need for a great weekend stay!!"
United States
lizbeth g.
The price is AU$309
includes taxes & fees
1 Apr - 2 Apr
Huge 1br apt, baby-friendly, dogs, walkable downtown
9.2 out of 10, Wonderful, (89 reviews)
"This was an amazing cabin with a full kitchen so you could cook and enjoy the quiet."
United States
Lina A.
The price is AU$470
includes taxes & fees
3 Mar - 4 Mar
Antietam Creek - Quiet 2 Bedroom Cabin
9.2 out of 10, Wonderful, (31 reviews)
"Enjoyed the levels, hot tub, porch to get outside with my coffee, pet strolling area marvelous and washer/dryer."
United States
tracey b.
The price is AU$417
includes taxes & fees
9 Mar - 10 Mar
Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI
9.4 out of 10, Exceptional, (122 reviews)
"Great location — right on the Carroll Creek Walk and a stone’s throw from excellent restaurants and nice shops. "
United States
Darby R.
The price is AU$391
includes taxes & fees
23 Mar - 24 Mar
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
9.0 out of 10, Wonderful, (64 reviews)
"House was wonderful, and I loved how often Tony checked in! Will absolutely be staying here again!"
United States
Chelsey-Ann
The price is AU$437
includes taxes & fees
4 Mar - 5 Mar
Cozy cabin w/private hot tub & game room
10.0 out of 10, Exceptional, (5 reviews)
"Very clean, great amenities, comfortable!"
United States
James
The price is AU$689
includes taxes & fees
3 Mar - 4 Mar
Private A-Frame Near Harpers Ferry - Sauna, Fire Pit, 3BR/3BA, Pet-Friendly

Holiday Home in Frederick

Chic, pets, walk to downtown
10.0 out of 10, Exceptional, (15 reviews)
"We had a wonderful stay. The place has perfect and the location was close to everything downtown. The host was great. Will definitely stay there again."
United States
Patrick H.
The price is AU$368
includes taxes & fees
23 Mar - 24 Mar
Chic, pets, walk to downtown
9.8 out of 10, Exceptional, (31 reviews)
"Would come back anytime, very scenic and easy check-in process"
United States
Mark F.
The price is AU$527
includes taxes & fees
3 Mar - 4 Mar
Rebels Rest - Cabin with Enchanting Sunset Views!
9.8 out of 10, Exceptional, (65 reviews)
"Beautiful home, quiet and peaceful."
United States
Dina A.
The price is AU$520
includes taxes & fees
5 Mar - 6 Mar
Blue Ridge Getaway - Sunset Views, A.T. 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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Top Shepherdstown Hotel Reviews

Find out more about Shepherdstown

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$150 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?

Riverside cottage, minutes from historic Harpers Ferry! Private river access!: This holiday home rental outside of Shepherdstown offers a fireplace, a balcony and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. 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 10 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 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.