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

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Shepherdstown cottages

A living room with a dining table, chairs, a sofa, and a television.

1. Quaint Mini Cottage in Shepherdstown - Walking Distance

Quaint Mini Cottage in Shepherdstown - Walking Distance
Shepherdstown
9.8 out of 10, Exceptional, (25 reviews)
"Great location and home base for visiting Shepherdstown, Harpers Ferry, and Sharpsburg. Perfect for a couple."
United States
Virginia W.
The price is ￥18,970
￥35,006 total
includes taxes & fees
Oct 18 - Oct 19
Quaint Mini Cottage in Shepherdstown - Walking Distance
A bedroom with a bed, a table, and a view of the outdoors.

2. The Carriage House at Carrot Top Cottage

The Carriage House at Carrot Top Cottage
Harpers Ferry
9.8 out of 10, Exceptional, (54 reviews)
"Lovely little spot right off the AT and easy walk into historic HF. "
United States
Michael
The price is ￥22,011
￥34,907 total
includes taxes & fees
Nov 9 - Nov 10
The Carriage House at Carrot Top Cottage
A two-story house with a covered porch and a wooden fence.

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

Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Harpers Ferry
9.8 out of 10, Exceptional, (34 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.
The price is ￥30,778
￥53,671 total
includes taxes & fees
Nov 3 - Nov 4
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Exterior

4. Thoughtfully Design Cottage with Breathtaking Indoor and Outdoor in Maryland

Thoughtfully Design Cottage with Breathtaking Indoor and Outdoor in Maryland
Boonsboro
The price is ￥42,890
￥49,485 total
includes taxes & fees
Oct 20 - Oct 21
Thoughtfully Design Cottage with Breathtaking Indoor and Outdoor in Maryland
A white building with a red roof, a car parked in front, and a grassy yard.

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 ￥11,856
￥25,482 total
includes taxes & fees
Oct 18 - Oct 19
Bring Your Own Boat - Meticulously restored house on the Potomac River
A two-story house with a front porch, a garage, and a driveway.

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 ￥29,561
￥71,010 total
includes taxes & fees
Oct 20 - Oct 21
Large Family Home: 5 Mi to Dtwn Hagerstown!
Terrace/patio

7. 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 ￥92,280
￥117,394 total
includes taxes & fees
Oct 22 - Oct 23
Historic Stone Cottage with Hot Tub and Hammock, Minutes from Downtown Harpers Ferry, West Virginia
A hot tub with a view of a forested landscape during sunset.

8. 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, (28 reviews)
"The property was so nice with a beautiful view. We had a great time! Highly recommend this property."
United States
Anonymous traveler
The price is ￥18,653
￥64,234 total
includes taxes & fees
Oct 29 - Oct 30
Cottage w/ Hot Tub and 100-Mile Valley Views!
Property grounds

9. 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 ￥81,816
￥95,155 total
includes taxes & fees
Oct 21 - Oct 22
Enchanting Victorian Cottage Just Steps From All the Major Sites in Harpers Ferry, WV
A modern building with large windows, a deck, and a stone wall.

10. 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 ￥15,808
￥54,180 total
includes taxes & fees
Oct 21 - Oct 22
Woodsy Retreat with a Hot Tub and Seasonal Views!
A hot tub on a deck with a view of a lake and forest.

11. Peaceful Lakefront Cottage with Mountain Views!

Peaceful Lakefront Cottage with Mountain Views!
Harpers Ferry
9.8 out of 10, Exceptional, (42 reviews)
"Clean house. Host was able to accessible. Hot tub worked and clean. Kitchen had everything we needed. Great place to stay and relax"
United States
Lisa h.
The price is ￥18,179
￥67,013 total
includes taxes & fees
Nov 4 - Nov 5
Peaceful Lakefront Cottage with Mountain Views!
A covered deck with a table and chairs, overlooking a river and autumn foliage.

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

Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Harpers Ferry
10.0 out of 10, Exceptional, (28 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 ￥24,344
￥81,528 total
includes taxes & fees
Oct 21 - Oct 22
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
A covered outdoor area with a hot tub, wooden benches, and a view of a snowy landscape with trees and a fence.

13. 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, (26 reviews)
"Fun place to stay!!!"
United States
Theresa R.
The price is ￥35,568
￥62,535 total
includes taxes & fees
Oct 19 - Oct 20
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Terrace/patio

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 ￥62,721
￥79,799 total
includes taxes & fees
Oct 19 - Oct 20
Peaceful Hedgesville Cottage with Hot Tub, Fireplace & Resort Amenities in West Virginia
A kitchen with a dishwasher, a sink, and a stove. There are pots hanging above the sink and a window with a view of greenery outside.

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

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Frederick
10.0 out of 10, Exceptional, (71 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 ￥22,922
￥46,751 total
includes taxes & fees
Nov 3 - Nov 4
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
A wooden deck with a table and chairs, overlooking a forested area with string lights.

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 ￥26,339
￥69,251 total
includes taxes & fees
Oct 27 - Oct 28
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.
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Top Shepherdstown Hotel Reviews

Quality Inn Shepherdstown

Quality Inn Shepherdstown

10/10 Excellent
"Great"
Terry 1-night trip
Posted 5 hours ago
Quality Inn Shepherdstown

Find out more about Shepherdstown

Shepherdstown Cottages information

Number of reviews
331
Accommodation
86 Cottages
Lowest Price
￥25,482
Highest Price
￥117,394

Frequently asked questions

How much do cottages in Shepherdstown cost?
Cottages in Shepherdstown range between ￥25,482 and ￥117,394 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 vacation 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.