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Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Compare 61 Cottages in Shepherdstown with updated reviews, rates, and availability.

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Private kitchen

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

10.0 out of 10, Exceptional, (32)
"In a town with relatively few accommodations, this house is a standout. A new kitchen and bathroom enhance the charm of the wood floors and original staircase. It's well-located too--just a few walkable blocks from downtown Frederick. The three of us each had our own bedroom and the layout was perfect. Ed was so responsive both before and during our stay. I highly recommend this property if you're looking to spend time in Frederick."
The price is AED 463
AED 981 total
includes taxes & fees
23 Feb - 24 Feb
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, (33)
"Absolutely a great place and location. Our plans completely changed after getting 6” of snow and then a deep freeze, but we were comfortable and were able to prepare all our meals with the equipment and utensils provided. Communication was great, check in easy and no extravagant check out demands. Can’t wait to come back "
Carrot Top Cottage surrounded by National Park
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Terrace/patio

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 AED 918
AED 1,553 total
includes taxes & fees
24 Feb - 25 Feb
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Charming Cottage in Purcellville on 12 Gorgeous Acres with 2 Acre Stocked Pond
Exterior

Charming Cottage in Purcellville on 12 Gorgeous Acres with 2 Acre Stocked Pond

Charming Cottage in Purcellville on 12 Gorgeous Acres with 2 Acre Stocked Pond
The Carriage House at Carrot Top Cottage
Terrace/patio

The Carriage House at Carrot Top Cottage

9.8 out of 10, Exceptional, (31)
"We enjoyed the stay and it was an easy walk to the places we wanted to go!"
The price is AED 360
AED 626 total
includes taxes & fees
24 Feb - 25 Feb
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 AED 606
AED 1,093 total
includes taxes & fees
23 Feb - 24 Feb
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Lovettsville Cottage in Heart of Wine Country
Lovettville Vacation Rental | 1BR | 2BA | 2 Stories | 3 Steps Required

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
Private Waterfront Deck with swing goes with rental

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!
Property grounds

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 AED 444
AED 1,698 total
includes taxes & fees
27 Feb - 28 Feb
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Lake View Retreat - Cottage Near a Peaceful Lake!
This home is just a short walk to Lake Shannondale, and has wintertime views of the lake! Spend your mornings on the front porch, or take a leisurely stroll around the lake.

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 AED 367
AED 1,288 total
includes taxes & fees
23 Feb - 24 Feb
Lake View Retreat - Cottage Near a Peaceful Lake!
Peaceful Lakefront Cottage with Mountain Views!
Enjoy a soak in the hot tub!

Peaceful Lakefront Cottage with Mountain Views!

10.0 out of 10, Exceptional, (23)
"Wintertime visit. Very peaceful. "
The price is AED 411
AED 1,392 total
includes taxes & fees
25 Feb - 26 Feb
Peaceful Lakefront Cottage with Mountain Views!
Quiet Cottage on Five+ Acres of Woods Close to All That Berkeley Springs Offers
Exterior

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

9.8 out of 10, Exceptional, (6)
"Home was beautiful, super clean, comfy beds, big screen TV, well-equipped, beautifully decorated and very secluded. Host were great. They even had a highchair & crib for our 18-mo. old. On the other hand, and not such a big deal, but there was no wood for the fire pit as promised, none of the outdoor lights worked, and we wish we didn't have to take the garbage with us on our long trip back. Otherwise, we had a good time in this scenic, quiet, secluded home."
The price is AED 650
AED 1,542 total
includes taxes & fees
23 Feb - 24 Feb
Quiet Cottage on Five+ Acres of Woods Close to All That Berkeley Springs Offers
Cottage at Gray Fox- Many Attraction- Pet Friendly
Private kitchen

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 AED 367
AED 1,378 total
includes taxes & fees
23 Feb - 24 Feb
Cottage w/ Hot Tub and 100-Mile Valley Views!
Magical Treehouse in Woods, Close many Wineries & Breweries, Pet Friendly!
Exterior

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!
Living area

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 AED 367
AED 1,239 total
includes taxes & fees
25 Feb - 26 Feb
Woodsy Retreat with a Hot Tub and Seasonal Views!
Entire Mountain Cottage Near Scenic Hiking Trails, Your Getaway Retreat!
Exterior

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
Property grounds

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 AED 275
AED 592 total
includes taxes & fees
23 Feb - 24 Feb
Bring Your Own Boat - Meticulously restored house on the Potomac River
Lock Keepers Cottage on C&O Canal/Potomac River
come sit a spell

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
Exterior

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
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
Exterior

❤️ 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 AED 162
AED 403 total
includes taxes & fees
3 Mar - 4 Mar
❤️ 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
Graycliff Hall: Riverfront Estate w/ Heli Pad, Private Chef, Hot Tub
Welcome To Graycliff Hall. Your beautiful riverside estate.

Graycliff Hall: Riverfront Estate w/ Heli Pad, Private Chef, Hot Tub

8.0 out of 10, Very Good, (1)
"Our family had an unforgettable New Year's holiday at this incredible rental property! From the moment we arrived, we were amazed by the beautiful house, its spaciousness, and the plethora of facilities available to accommodate everyone in our group. The property was clean, well-organized, and tastefully decorated, making it a warm and inviting space for our celebration.The true gem of our stay was the exceptional hospitality provided by the property's management, especially the remarkable Miss...
Graycliff Hall: Riverfront Estate w/ Heli Pad, Private Chef, Hot Tub
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 AED 275 and AED 918 per night. These properties offer a chance to reconnect with nature — 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.
How many cottages are there in Shepherdstown?
There are 61 cottages in Shepherdstown. No matter if you’re traveling with the kids or planning a weekend retreat with friends, Expedia will help you find the ideal property to escape the hustle and bustle.
Why book your cottage in Shepherdstown with Expedia?
We think that vacations should be simple, so if you’re looking for cottages in Shepherdstown at an affordable rate, Expedia has you covered. Keep the budget in check and choose a cheap option far from the hustle and bustle, or splurge on an upscale cottage to spoil the ones you love most.
How can I find cheap cottages in Shepherdstown?
Expedia is here to help you easily source cheap cottages in Shepherdstown. To lock in your ideal stay in a few quick keystrokes, try out the filter tool to refine your search results by budget, star rating and amenities.