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

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

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, (24 reviews)
"Host let us in a bit early which was nice!"
United States
John
The price is CA $166
CA $304 total
includes taxes & fees
Sep 6 - Sep 7
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, (52 reviews)
"Lovely little spot right off the AT and easy walk into historic HF. "
United States
Michael
The price is CA $191
CA $304 total
includes taxes & fees
Sep 10 - Sep 11
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, (31 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 CA $302
CA $517 total
includes taxes & fees
Sep 7 - Sep 8
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
A white building with a red roof, a car parked in front, and a grassy yard.

4. 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)
"Just what I needed. Great place."
United States
Shannon W.
The price is CA $104
CA $223 total
includes taxes & fees
Oct 1 - Oct 2
Bring Your Own Boat - Meticulously restored house on the Potomac River

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

Thoughtfully Design Cottage with Breathtaking Indoor and Outdoor in Maryland
Boonsboro
The price is CA $362
CA $430 total
includes taxes & fees
Sep 7 - Sep 8
Thoughtfully Design Cottage with Breathtaking Indoor and Outdoor in Maryland
A modern building with large windows, a deck, and a stone wall.

6. 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, (26 reviews)
"Great house. Comfortable beds, had everything we needed. Loved the hot tube and wood burner. "
United States
Amy P.
The price is CA $138
CA $477 total
includes taxes & fees
Sep 10 - Sep 11
Woodsy Retreat with a Hot Tub and Seasonal Views!
A hot tub on a deck with a view of a lake and forest.

7. Peaceful Lakefront Cottage with Mountain Views!

Peaceful Lakefront Cottage with Mountain Views!
Harpers Ferry
9.8 out of 10, Exceptional, (39 reviews)
"Excellent property for a relaxing getaway. Very clean. Host very responsive."
United States
Brad C.
The price is CA $186
CA $632 total
includes taxes & fees
Sep 8 - Sep 9
Peaceful Lakefront Cottage with Mountain Views!
A covered deck with a table and chairs, overlooking a river and autumn foliage.

8. 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 CA $194
CA $690 total
includes taxes & fees
Sep 21 - Sep 22
Art Docko - Lakefront Artist Retreat w/ Hot Tub!

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 CA $504
CA $571 total
includes taxes & fees
Sep 13 - Sep 14
Enchanting Victorian Cottage Just Steps From All the Major Sites in Harpers Ferry, WV
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.

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

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Frederick
10.0 out of 10, Exceptional, (69 reviews)
"Wonderfully remodeled spot, great amenities, extremely close to downtown, was perfect for our trip!"
United States
Andrew F.
The price is CA $175
CA $381 total
includes taxes & fees
Sep 14 - Sep 15
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
A wooden deck with a table and chairs, overlooking a forested area with string lights.

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

Country Road Cottage-Mountain Views + Private Hot Tub + Sauna + Game Room
Berkeley Springs
10.0 out of 10, Exceptional, (3 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 CA $200
CA $572 total
includes taxes & fees
Sep 7 - Sep 8
Country Road Cottage-Mountain Views + Private Hot Tub + Sauna + Game Room
A covered outdoor area with a hot tub, wooden benches, and a view of a snowy landscape with trees and a fence.

12. 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, (24 reviews)
"Very relaxing stay! Clean hot tub!! "
United States
Mara H.
The price is CA $311
CA $545 total
includes taxes & fees
Sep 6 - Sep 7
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
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

Mirror Villas - Modern Retreat with private hot tubs and mountain view

Mirror Villas - Modern Retreat with private hot tubs and mountain view

10/10 Excellent
"If you are anywhere on the East Coast and looking for a nice getaway or time to reset and just chill...you should definitely make this a spot to visit. I thoroughly enjoyed my time and wished I could have extended my stay. The mirror cabins were gorgeous. The attention to detail was lovely. My partner and I loved having the ability to barbecue, dip in the hot tub, and next time I'm booking the room with the sauna! My fiance, he loved looking at all Miami Vice episodes on the projector! You definitely want to make a trip over to this part of Pennsylvania and oddly enough, you're close to the Maryland and West Virginia borders, so you can make it a 3 state trip almost in one day! We enjoyed our time and will definitely will be back. Note: there is a lot of gravel to ride up on so make sure if you are not riding a 4wd or awd that your tires are solid! And like another guest said just be careful walking around the cabin in your knickers (or not) with the lights on at night! Make your booking now!"
Renee 3-night trip
Posted 21 hours ago
Mirror Villas - Modern Retreat with private hot tubs and mountain view

Find out more about Shepherdstown

Shepherdstown Cottages information

Number of reviews
8,149
Accommodation
86 Cottages
Lowest Price
CA $92
Highest Price
CA $329

Frequently asked questions

How much do cottages in Shepherdstown cost?
Cottages in Shepherdstown range between CA $92 and CA $329 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.

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