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

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

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.
$198 nightly
The price is $220
Nov 1 - Nov 2
Total with taxes and fees
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, (55 reviews)
"Lovely little spot right off the AT and easy walk into historic HF. "
United States
Michael
$199 nightly
The price is $222
Nov 9 - Nov 10
Total with taxes and fees
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, (35 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.
$305 nightly
The price is $340
Nov 1 - Nov 2
Total with taxes and fees
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
A residential area with houses, roads, and green fields.

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

Thoughtfully Design Cottage with Breathtaking Indoor and Outdoor in Maryland
Boonsboro
$294 nightly
The price is $312
Nov 2 - Nov 3
Total with taxes and fees
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.
$145 nightly
The price is $161
Oct 30 - Oct 31
Total with taxes and fees
Bring Your Own Boat - Meticulously restored house on the Potomac River
A hot tub with a view of a forested landscape during sunset.

6. 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.
$357 nightly
The price is $397
Oct 29 - Oct 30
Total with taxes and fees
Cottage w/ Hot Tub and 100-Mile Valley Views!
A two-story house with a front porch, a garage, and a driveway.

7. 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
$401 nightly
The price is $449
Nov 5 - Nov 6
Total with taxes and fees
Large Family Home: 5 Mi to Dtwn Hagerstown!
A two-story house with a porch, a front door, and a number '190' sign.

8. 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
$513 nightly
The price is $549
Oct 29 - Oct 30
Total with taxes and fees
Enchanting Victorian Cottage Just Steps From All the Major Sites in Harpers Ferry, WV
A historic building with a brick facade, multiple windows, and a covered porch area.

9. 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
$673 nightly
The price is $750
Nov 9 - Nov 10
Total with taxes and fees
Historic Stone Cottage with Hot Tub and Hammock, Minutes from Downtown Harpers Ferry, West Virginia
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.
$392 nightly
The price is $437
Nov 15 - Nov 16
Total with taxes and fees
Woodsy Retreat with a Hot Tub and Seasonal Views!
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.

11. 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.
$263 nightly
The price is $278
Nov 3 - Nov 4
Total with taxes and fees
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
A hot tub on a deck with a view of a lake and forest.

12. 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.
$454 nightly
The price is $505
Nov 10 - Nov 11
Total with taxes and fees
Peaceful Lakefront Cottage with Mountain Views!
A covered deck with a table and chairs, overlooking a river and autumn foliage.

13. 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.
$538 nightly
The price is $599
Nov 12 - Nov 13
Total with taxes and fees
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.

14. 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.
$344 nightly
The price is $392
Nov 1 - Nov 2
Total with taxes and fees
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
A wooden deck with a table and chairs, overlooking a forested area with string lights.

15. 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.
$386 nightly
The price is $430
Nov 1 - Nov 2
Total with taxes and fees
Mountain Views + Private Hot Tub + Sauna + Game Room - Country Road Cottage
Exterior

16. 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
$454 nightly
The price is $505
Nov 3 - Nov 4
Total with taxes and fees
Peaceful Hedgesville Cottage with Hot Tub, Fireplace & Resort Amenities in West Virginia
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

Best Western Historic Frederick

Best Western Historic Frederick

10/10 Excellent
"My room was amazing! modern, attractive and clean. The firmness of the bed was perfect. I slept well."
Malika 1-night trip
Posted 2 hours ago
Best Western Historic Frederick

Find out more about Shepherdstown

Shepherdstown Cottages information

Number of reviews
362
Accommodation
89 Cottages
Lowest Price
$161
Highest Price
$750

Frequently asked questions

How much do cottages in Shepherdstown cost?
Cottages in Shepherdstown range between $161 and $750 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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