Search Shepherdstown Cottage Rentals from CA $109

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Check prices for these dates

Next weekend
Mar 14 - Mar 16
In two weeks
Mar 21 - Mar 23
In one month
Apr 4 - Apr 6
In two months
May 2 - May 4

Browse Select Shepherdstown Cottages

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Fridge, microwave, oven, stovetop

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

10.0 out of 10, Exceptional, (34)
"The house is very well preserved classical duplex home on a road with plenty of parking with easy walking access to Market street just a couple blocks away. Its ideal for our type of stay when we want to check out the city."
The price is CA $172
CA $376 total
includes taxes & fees
Mar 13 - Mar 14
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Carrot Top Cottage surrounded by National Park
Exterior

Carrot Top Cottage surrounded by National Park

10.0 out of 10, Exceptional, (34)
"Very well stocked, clean, great communication from host, convenient, would definitely recommend "
Carrot Top Cottage surrounded by National Park
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Interior

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

10.0 out of 10, Exceptional, (1)
"We had a a great experience at this cabin getaway. The property was immaculate, cozy and well-equipped. The host was incredibly responsive and thoughtful. We can't wait to come back!"
The price is CA $362
CA $610 total
includes taxes & fees
Mar 6 - Mar 7
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
The Carriage House at Carrot Top Cottage
Aerial view

The Carriage House at Carrot Top Cottage

9.8 out of 10, Exceptional, (33)
"Harpers Ferry is a must visit, and the Carrot Top Cottage was the perfect location to be completely immersed in the history and quaitness you'd expect to find.The hosts are 2nd to none and quick to act when situations out of their control occurred. The power outage literally set the town back into the early 19th century. We will definitely be visiting again, and would recommend to coupmes of all ages."
The price is CA $142
CA $247 total
includes taxes & fees
Mar 6 - Mar 7
The Carriage House at Carrot Top Cottage
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Exterior

Amazing dog-friendly cottage. Walk 2 Harpers Ferry

2.0 star property
9.8 out of 10, Exceptional, (9)
"What a lovely, cozy, clean property! The location was in the heart of Harper’s Ferry. Everything advertised was exactly as described, even nicer, inside and out! Cathy, our property manager was communicative and helpful. We will be back!!"
The price is CA $239
CA $436 total
includes taxes & fees
Mar 5 - Mar 6
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Lovettsville Cottage in Heart of Wine Country
TV, Netflix, streaming services

Lovettsville Cottage in Heart of Wine Country

9.8 out of 10, Exceptional, (32)
"Perfect for the weekend getaway we were looking for! Beautiful guest home that was very clean and was well stocked with anything we might need. Only one issue was there were lots of stink bugs in the house but I imagine in the winter that would be more of a problem then in the warmer months. "
Lovettsville Cottage in Heart of Wine Country
RIVERKEEPER INN, Waterfront Property on the Potomac River
View from property

RIVERKEEPER INN, Waterfront Property on the Potomac River

9.2 out of 10, Wonderful, (116)
"The hosts are wonderful. I had a great time in their cozy, clean and beautiful place. Highly recommend for a visit to beautiful and historic WV.I particularly appreciated their fondness for dogs. Mine had a great time too!"
RIVERKEEPER INN, Waterfront Property on the Potomac River
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Outdoor dining

Art Docko - Lakefront Artist Retreat w/ Hot Tub!

10.0 out of 10, Exceptional, (16)
"Check in was seamless. The place was perfect for three couples with all the master suites. "
The price is CA $329
CA $886 total
includes taxes & fees
Mar 10 - Mar 11
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Lake View Retreat - Cottage Near a Peaceful Lake!
Property grounds

Lake View Retreat - Cottage Near a Peaceful Lake!

9.6 out of 10, Exceptional, (17)
"Beautiful location to relax and enjoy friends. This house was huge. Plenty of room for the 3 of us...could have been 8, lol. "
The price is CA $145
CA $508 total
includes taxes & fees
Mar 6 - Mar 7
Lake View Retreat - Cottage Near a Peaceful Lake!
Peaceful Lakefront Cottage with Mountain Views!
Fridge, microwave, oven, stovetop

Peaceful Lakefront Cottage with Mountain Views!

10.0 out of 10, Exceptional, (23)
"Wintertime visit. Very peaceful. "
The price is CA $299
CA $742 total
includes taxes & fees
Mar 20 - Mar 21
Peaceful Lakefront Cottage with Mountain Views!
Quiet Cottage on Five+ Acres of Woods Close to All That Berkeley Springs Offers
Exterior detail

Quiet Cottage on Five+ Acres of Woods Close to All That Berkeley Springs Offers

9.8 out of 10, Exceptional, (7)
"Good place for a nice quite weekend."
The price is CA $256
CA $615 total
includes taxes & fees
Mar 23 - Mar 24
Quiet Cottage on Five+ Acres of Woods Close to All That Berkeley Springs Offers
Cottage at Gray Fox- Many Attraction- Pet Friendly
Aerial view

Cottage at Gray Fox- Many Attraction- Pet Friendly

10.0 out of 10, Exceptional, (21)
"Wonderful property for a girls' getaway! The owners are very responsive to messages and communicated well with us. Clean, comfy beds, had everything we needed. The hot tub was a plus on a snowy weekend."
Cottage at Gray Fox- Many Attraction- Pet Friendly
Cottage w/ Hot Tub and 100-Mile Valley Views!
Outdoor spa tub

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

10.0 out of 10, Exceptional, (15)
"The view of this house is amazing! Absolutely beautiful!"
The price is CA $145
CA $544 total
includes taxes & fees
Mar 6 - Mar 7
Cottage w/ Hot Tub and 100-Mile Valley Views!
Magical Treehouse in Woods, Close many Wineries & Breweries, Pet Friendly!
Property grounds

Magical Treehouse in Woods, Close many Wineries & Breweries, Pet Friendly!

10.0 out of 10, Exceptional, (1)
"This treehouse was so dreamy and private! I hope we get to stay here again some time soon!"
Magical Treehouse in Woods, Close many Wineries & Breweries, Pet Friendly!
Woodsy Retreat with a Hot Tub and Seasonal Views!
Terrace/patio

Woodsy Retreat with a Hot Tub and Seasonal Views!

9.8 out of 10, Exceptional, (17)
"We love it! everything was perfect 🤗 we definitely coming back ❤️"
The price is CA $145
CA $491 total
includes taxes & fees
Mar 11 - Mar 12
Woodsy Retreat with a Hot Tub and Seasonal Views!
Entire Mountain Cottage Near Scenic Hiking Trails, Your Getaway Retreat!
Interior

Entire Mountain Cottage Near Scenic Hiking Trails, Your Getaway Retreat!

10.0 out of 10, Exceptional, (3)
"Cozy remodeled property. Plenty of space for 9 adults and teens to celebrate Christmas. George is a great host. Highly recommend. "
Entire Mountain Cottage Near Scenic Hiking Trails, Your Getaway Retreat!
Bring Your Own Boat - Meticulously restored house on the Potomac River
Game room

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

10.0 out of 10, Exceptional, (3)
"Clean, everything you need is there. Peaceful."
The price is CA $109
CA $234 total
includes taxes & fees
Mar 5 - Mar 6
Bring Your Own Boat - Meticulously restored house on the Potomac River
Lock Keepers Cottage on C&O Canal/Potomac River

Lock Keepers Cottage on C&O Canal/Potomac River

10.0 out of 10, Exceptional, (48)
"We had a great time. Very comfortable like home. "
Lock Keepers Cottage on C&O Canal/Potomac River
Cozy Stone Cottage in Round Hill, VA
Fridge, microwave, oven, stovetop

Cozy Stone Cottage in Round Hill, VA

10.0 out of 10, Exceptional, (2)
"We had an excellent stay at cottage! It was perfect for a short weekend away with girlfriends. It was quaint and historic but didn't lack modern day comforts. Highly recommend for anyone looking for a few days away, with easy access to all Round Hill & Purcellville has to offer. "
Cozy Stone Cottage in Round Hill, VA
Cozy Mountain Cottage - Perfect for Friends, Family
Exterior

Cozy Mountain Cottage - Perfect for Friends, Family

10.0 out of 10, Exceptional, (13)
"We had a great time over Thanksgiving. The house , yard and host were all great. I woood definitely stay here again. "
Cozy Mountain Cottage - Perfect for Friends, Family
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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Other property types in Shepherdstown

❤️ Secluded 1940s Romantic Tiny House on the River
Beach

❤️ Secluded 1940s Romantic Tiny House on the River

10.0 out of 10, Exceptional, (53)
"The cabin was perfect for a few days of writing and reflecting! Everything was very clean and it was easy communicating with the owner. The house is not "secluded" as there are neighboring houses on two sides and if I hadn't brought an ax/saw to cut my own dry wood enjoying a fire wouldn't have been possible. But overall a lovely stay and I look forward to going again!"
The price is CA $104
CA $204 total
includes taxes & fees
Mar 30 - Mar 31
❤️ Secluded 1940s Romantic Tiny House on the River
Charming Cabin in the Woods with River Access
Exterior

Charming Cabin in the Woods with River Access

9.8 out of 10, Exceptional, (17)
"Great experience. Cabin is as shown, very comfortable, easy access. 10 min to Shepherdstown, lots of great restaurants and shops there. Our dates ended up being over the severe cold/snow in January 2025, so we didn't do much hiking or anything on the river, but it was a lovely environment, very peaceful and cozy. Owners were super responsive when needed and very easy to work with. Would definitely go back in nicer weather! "
Charming Cabin in the Woods with River Access
Welcome to this patch of serenity on the river's edge, to this hideaway.
Dining

Welcome to this patch of serenity on the river's edge, to this hideaway.

9.8 out of 10, Exceptional, (60)
"Loved everything. Quiet, peaceful….loved the small deck off the upstairs bedroom."
Welcome to this patch of serenity on the river's edge, to this hideaway.
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.

Frequently asked questions

How much do cottages in Shepherdstown cost?
Cottages in Shepherdstown range between CA $109 and CA $362 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.