A street lined with brick buildings, including a bank and a restaurant.

Search Cottages in Shepherdstown

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Shepherdstown cottages

1. Quaint Mini Cottage in Shepherdstown - Walking Distance

Quaint Mini Cottage in Shepherdstown - Walking Distance
Shepherdstown
9.8 out of 10, Exceptional, (27 reviews)
"Absolutely adorable, perfect location and well appointed. Would absolutely stay here again. Highly recommend and maybe if you’re lucky you’ll meet the little black cat who visited us!!"
United States
Abigail
The price is €219
includes taxes & fees
15 Nov - 16 Nov
Quaint Mini Cottage in Shepherdstown - Walking Distance

2. Walk to Stores: Home in Historic Shepherdstown!

Walk to Stores: Home in Historic Shepherdstown!
3.0 star property
Shepherdstown
The price is €317
includes taxes & fees
19 Nov - 20 Nov
Walk to Stores: Home in Historic Shepherdstown!

3. The Carriage House at Carrot Top Cottage

The Carriage House at Carrot Top Cottage
Harpers Ferry
9.8 out of 10, Exceptional, (55 reviews)
"Very clean and convenient for seeing Harpers Ferry"
United States
Rich C.
The price is €192
includes taxes & fees
9 Nov - 10 Nov
The Carriage House at Carrot Top Cottage

4. Amazing dog-friendly cottage. Walk 2 Harpers Ferry

Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Harpers Ferry
9.8 out of 10, Exceptional, (36 reviews)
"We enjoyed our stay here so much and when we go back to Harper’s Ferry we hope to stay in the same place again"
United States
Zachary S.
Amazing dog-friendly cottage. Walk 2 Harpers Ferry

5. Bring Your Own Boat - Meticulously restored house on the Potomac River

Bring Your Own Boat - Meticulously restored house on the Potomac River
Hedgesville
9.6 out of 10, Exceptional, (14 reviews)
"Great little place to stay."
United States
Shannon W.
The price is €139
includes taxes & fees
5 Nov - 6 Nov
Bring Your Own Boat - Meticulously restored house on the Potomac River

6. Large Family Home: 5 Mi to Dtwn Hagerstown!

Large Family Home: 5 Mi to Dtwn Hagerstown!
3.0 star property
Williamsport
10.0 out of 10, Exceptional, (1 review)
"The place was just beautiful "
United States
Derrick
The price is €401
includes taxes & fees
5 Nov - 6 Nov
Large Family Home: 5 Mi to Dtwn Hagerstown!

7. Enchanting Victorian Cottage Just Steps From All the Major Sites in Harpers Ferry, WV

Enchanting Victorian Cottage Just Steps From All the Major Sites in Harpers Ferry, WV
Harpers Ferry
The price is €632
includes taxes & fees
17 Nov - 18 Nov
Enchanting Victorian Cottage Just Steps From All the Major Sites in Harpers Ferry, WV

8. Historic Stone Cottage with Hot Tub and Hammock, Minutes from Downtown Harpers Ferry, West Virginia

Historic Stone Cottage with Hot Tub and Hammock, Minutes from Downtown Harpers Ferry, West Virginia
Bolivar
The price is €759
includes taxes & fees
17 Nov - 18 Nov
Historic Stone Cottage with Hot Tub and Hammock, Minutes from Downtown Harpers Ferry, West Virginia

9. Woodsy Retreat with a Hot Tub and Seasonal Views!

Woodsy Retreat with a Hot Tub and Seasonal Views!
Harpers Ferry
9.8 out of 10, Exceptional, (29 reviews)
"Property was a great location for all we wanted to do during our vacation. The beach area was the perfect retreat for some relaxation after long days of hiking. Area is beautiful, house was comfortable (slept like a baby), and we had a great stay. Would definitely stay again."
United States
Rebecca N.
The price is €369
includes taxes & fees
19 Nov - 20 Nov
Woodsy Retreat with a Hot Tub and Seasonal Views!

10. Cottage w/ Hot Tub and 100-Mile Valley Views!

Cottage w/ Hot Tub and 100-Mile Valley Views!
Harpers Ferry
9.8 out of 10, Exceptional, (29 reviews)
"My husband and I went for a short trip. The communication was great and the house was perfect! We spent most of our time in the hot tub checking out the amazing view."
United States
Keri L.
The price is €398
includes taxes & fees
16 Nov - 17 Nov
Cottage w/ Hot Tub and 100-Mile Valley Views!

11. Art Docko - Lakefront Artist Retreat w/ Hot Tub!

Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Harpers Ferry
10.0 out of 10, Exceptional, (29 reviews)
"With bedrooms and sitting rooms on 3 floors, our 3-generation family enjoyed having space to gather together as well as space for time apart. The decks allowed for additional places to enjoy the beautiful surroundings. Lake access was great for swimming and kayaking."
United States
Lindy K.
The price is €441
includes taxes & fees
18 Nov - 19 Nov
Art Docko - Lakefront Artist Retreat w/ Hot Tub!

12. Peaceful Lakefront Cottage with Mountain Views!

Peaceful Lakefront Cottage with Mountain Views!
Harpers Ferry
9.8 out of 10, Exceptional, (42 reviews)
"The property was absolutely beautiful. The view of the lake was so pretty. Communication with the host was wonderful very informative. Very cozy and the house was beautiful inside."
United States
Tara G.
The price is €402
includes taxes & fees
18 Nov - 19 Nov
Peaceful Lakefront Cottage with Mountain Views!

13. Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Frederick
10.0 out of 10, Exceptional, (72 reviews)
"The house is very cute and a perfect fit for our needs. We appreciated how clean the house was too! It's conveniently located to some many restaurants and shops. We would gladly stay here again!"
United States
Sara W.
The price is €251
includes taxes & fees
8 Nov - 9 Nov
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

14. Peaceful Hedgesville Cottage with Hot Tub, Fireplace & Resort Amenities in West Virginia

Peaceful Hedgesville Cottage with Hot Tub, Fireplace & Resort Amenities in West Virginia
The Woods
The price is €477
includes taxes & fees
17 Nov - 18 Nov
Peaceful Hedgesville Cottage with Hot Tub, Fireplace & Resort Amenities in West Virginia

15. The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!

The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Hamilton
10.0 out of 10, Exceptional, (27 reviews)
"Fun place to stay!!!"
United States
Theresa R.
The price is €338
includes taxes & fees
5 Nov - 6 Nov
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!

16. Mountain Views + Private Hot Tub + Sauna + Game Room - Country Road Cottage

Mountain Views + Private Hot Tub + Sauna + Game Room - Country Road Cottage
Berkeley Springs
10.0 out of 10, Exceptional, (5 reviews)
"One of the best properties I’ve rented. Everything was better than described and the description was already stellar. Highly recommend and will likely rent again. "
United States
Cyndi P.
The price is €364
includes taxes & fees
10 Nov - 11 Nov
Mountain Views + Private Hot Tub + Sauna + Game Room - Country Road Cottage
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Shepherdstown Hotel Reviews

Find out more about Shepherdstown

Shepherdstown Cottages information

Number of reviews
366
Accommodation
88 Cottages
Lowest Price
€139
Highest Price
€759

Frequently asked questions

How much do cottages in Shepherdstown cost?
Cottages in Shepherdstown range between €139 and €759 per night. These retreats offer a chance to soak in nature's beauty — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why book your cottage in Shepherdstown with Expedia?
Expedia has some great cottages in Shepherdstown, so start packing for a memorable holiday on nature's doorstep. If you have a budget, choose how much you'd like to spend and your preferred property star rating. Or, make use of our filters to search for cottages with a pool or free WiFi. We'll help you find the perfect pad whatever your trip looks like.
How can I find cheap cottages in Shepherdstown?
With Expedia's filter tool, sourcing cheap cottages in Shepherdstown is a breeze. To discover stays that'll make your bank balance smile, tailor your search results by star rating, amenities and budget.
What is there to do in Shepherdstown near my cottage?
There are loads of impressive things to do and see in Shepherdstown. Check out well-known attractions like Shepherdstown Opera House, Shepherdstown Museum and Morgan's Grove Park. Cress Creek Golf Club, Rumsey Monument and Elmwood Cemetery are other must-do's.