Shepherdstown Holiday Rentals

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Holiday Rentals in Shepherdstown

Cabin in Shepherdstown

10.0 out of 10, Exceptional, (64)
"We truly loved this location and definitely will be back!"
United States
Astrid
The price is AU$163
includes taxes & fees
9 Dec - 10 Dec
❤️ Secluded 1940s Romantic Tiny House on the River

Chalet in Mercersburg

3.5 star property
9.6 out of 10, Exceptional, (4)
"Clean room, spacious intimate setting "
United States
Camille
The price is AU$875
includes taxes & fees
4 Dec - 5 Dec
Mirror Villas - Modern Retreat with private hot tubs and mountain view

Cabin in Berkeley Springs

9.6 out of 10, Exceptional, (86)
"We loved this little cabin! It was so cozy and just 20-30 minutes from anything in town. "
United States
Gabrielle B.
Hidden Gem in the woods with hot tub

Holiday Home in Harpers Ferry

9.8 out of 10, Exceptional, (133)
"Although I never met my hostess, the cottage stay was easy to book and just as advertised. Fantastic views, well stocked kitchen, and a personal greeting on wet board. Gas fireplace was warm and cozy."
United States
Karen
Riverside cottage, minutes from historic Harpers Ferry! Private river access!

Apartment in Martinsburg

9.8 out of 10, Exceptional, (20)
"Our family thoroughly our stay at this beautiful well-equipped house. Our family agreed this was our favorite vacation house. Great location on the Potomac River made better with all the available water toys. My Great-Grand Children enjoyed the fishing and even caught a few. We were slightly disappointed that the dock shown in one picture wasn't there. It was destroyed in a recent storm. "
United States
Anonymous traveller
Luxury Getaway on The Potomac

Holiday Home in Berkeley Springs

10.0 out of 10, Exceptional, (46)
"What an absolutely gorgeous place with unbelievable views off the balcony! We really enjoyed our spring break there with lots of hiking outings and zip lining not too far away. "
United States
Cintia U.
✨Luxurious Mountaintop Lodge🏔️WOW Scenic Views🫧Hot Tub under the BIG SKY STARS 🌟

Cabin in Middletown

9.6 out of 10, Exceptional, (110)
"Beautiful cabin with an adorable mini oven, great TV, creature comforts of robes and throws. Best sleep I’ve ever had in the quiet."
United States
Sharon H.
The price is AU$305
includes taxes & fees
30 Nov - 1 Dec
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

Cabin in Berkeley Springs

10.0 out of 10, Exceptional, (62)
"Couldn't ask for a nicer place to stay peaceful, quiet with a great view. Wildlife is abundant and beautiful everything that you could need or want to relax Bill and Patty were excellent hosts looking forward to visiting again"
United States
Robert Z.
Private, light filled retreat space... with your own pickleball court!

Cabin in Gerrardstown

8.2 out of 10, Very good, (11)
"Our team had a fantastic stay at the chalet cabin rental. The hot tub, BBQ grille, and fire pit were all great amenities, and the wifi was a nice bonus. The huge primary suite upstairs and reading loft provided enough space for everyone to have their own space. We would highly recommend this chalet for work retreats or any group getaway"
United States
Manuel T.
The price is AU$451
includes taxes & fees
21 Dec - 22 Dec
Fireplace, Wraparound Deck, & WiFi at Chalet Cabin

Cottage in Berkeley Springs

9.8 out of 10, Exceptional, (18)
"Can't wait to come back to this beautiful home with my family! Amazing experience! "
United States
Brandon L.
The price is AU$646
includes taxes & fees
28 Dec - 29 Dec
Quiet Cottage on Five+ Acres of Woods Close to All That Berkeley Springs Offers

Holiday Home in Harpers Ferry

9.6 out of 10, Exceptional, (101)
"The house was beyond expectations."
United States
Eddie J.
The price is AU$611
includes taxes & fees
1 Dec - 2 Dec
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!

Cottage in Harper's Ferry

9.4 out of 10, Exceptional, (131)
"Beautiful location right on the Potomac River."
United States
Diane
RIVERKEEPER INN, Waterfront Property on the Potomac River

Cabin in Harpers Ferry

9.2 out of 10, Wonderful, (9)
"Very charming and spacious silo! Very quiet and comfortable. Highly recommend and would definitely stay again!"
United States
Lauren M.
The price is AU$461
includes taxes & fees
11 Dec - 12 Dec
Wild And Wonderful Silos

Apartment in Brunswick

10.0 out of 10, Exceptional, (21)
"Absolutely loved staying in this historic apartment! The hosts are incredibly friendly and the area is very walkable with local food and shops within a quarter to half mile. Such a great experience here, can’t recommend it enough and can’t wait to stay again!"
United States
Alicia
The price is AU$290
includes taxes & fees
9 Dec - 10 Dec
Beautiful, Historic, Hiking, Biking and C&O Canal

Holiday Home in Charles Town

9.6 out of 10, Exceptional, (65)
"We had a great time! The house overlooks the river and we loved the hot tub and fire pit! "
United States
Cherilyn M.
The price is AU$627
includes taxes & fees
11 Dec - 12 Dec
Terra Alta - Incredible River Views and Hot Tub!

Holiday Home in Berkeley Springs

10.0 out of 10, Exceptional, (65)
"This place is amazing"
United States
Mike A.
Sleepy Creek - hot tub, pets, grill, fire pit, wifi, screen porch, creekside

Holiday Home in Harpers Ferry

8.2 out of 10, Very good, (29)
"Very nice. Loved the location. Arcade did not work and no propane for the fire pit but overall amazing."
United States
Terry K.
Cozy Cabin w/ Hot Tub & Fire Pit perfect for up to 8 people

Cabin in Harpers Ferry

9.6 out of 10, Exceptional, (25)
"Great stay "
United States
Seth W.
The price is AU$677
includes taxes & fees
8 Dec - 9 Dec
The Oculus - Huge Cabin with a Hot Tub!

Cabin in Harpers Ferry

10.0 out of 10, Exceptional, (80)
"Absolutely delightful!"
United States
John M.
The price is AU$436
includes taxes & fees
1 Dec - 2 Dec
Cozy Mountain Cabin w/ Steam Shower! Family Friendly.

Cabin in Middletown

10.0 out of 10, Exceptional, (128)
"Great place to stay. Very quiet. Just wish there would have been a king size bed, otherwise loved it"
United States
Corinne R.
Countryside Cabin with Mountain Views near Surreybrooke Gardens
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$163 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 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 Cress Creek Country Club Golf Course 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.