Search Shepherdstown Cottage Rentals

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 17 - Oct 19
In two months
Nov 28 - Nov 30
In three months
Dec 26 - Dec 28
In four months
Jan 23 - Jan 25

Cottages in Shepherdstown

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

10.0 out of 10, Exceptional, (14)
"extremely quiet cabin in the woods"
The price is ￥23,375
￥62,674 total
includes taxes & fees
Oct 3 - Oct 4
Quiet Cottage on Five+ Acres of Woods Close to All That Berkeley Springs Offers
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
Quaint Mini Cottage in Shepherdstown - Walking Distance
Dining

Quaint Mini Cottage in Shepherdstown - Walking Distance

9.0 out of 10, Wonderful, (6)
"Great, easy to find location. Nancy was a great communicator A wonderful option for us, as we were in the area for a wedding in Sharpsburg where overnight accommodations were a bit slim. Shepherdstown was a cute town with lots of cute local shops and places to eat. Would stay here again! "
Quaint Mini Cottage in Shepherdstown - Walking Distance
Cottage w/ Hot Tub and 100-Mile Valley Views!
Property grounds

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

10.0 out of 10, Exceptional, (19)
"Pretty cabin with a wonderful view, especially from the hot tub. We will return!"
The price is ￥14,792
￥55,816 total
includes taxes & fees
Oct 9 - Oct 10
Cottage w/ Hot Tub and 100-Mile Valley Views!
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Property grounds

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

9.8 out of 10, Exceptional, (6)
"It was a great place to starve whole experience was perfect. "
The price is ￥33,077
￥56,647 total
includes taxes & fees
Oct 5 - Oct 6
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Carrot Top Cottage surrounded by National Park
Exterior

Carrot Top Cottage surrounded by National Park

10.0 out of 10, Exceptional, (46)
"The home was impeccably clean, quiet, comfortable, and homey. We enjoyed our stay so much. The home was wonderfully decorated. "
Carrot Top Cottage surrounded by National Park
Charming 2-Bedroom Cottage in Loudoun Co, VA on 12 Gorgeous Acres w/ 2-Acre Pond
Property grounds

Charming 2-Bedroom Cottage in Loudoun Co, VA on 12 Gorgeous Acres w/ 2-Acre Pond

9.8 out of 10, Exceptional, (7)
"Nice and convenient stay for nearby wedding."
Charming 2-Bedroom Cottage in Loudoun Co, VA on 12 Gorgeous Acres w/ 2-Acre Pond
Raspberry Retreat Cottage
Outdoor dining

Raspberry Retreat Cottage

10.0 out of 10, Exceptional, (3)
"Cute property. Beautiful scenery. This property worked well for our family."
Raspberry Retreat Cottage
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Fridge, microwave, oven, stovetop

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

10.0 out of 10, Exceptional, (54)
"The house was clean and the beds were very comfortable! Great stay overall "
The price is ￥17,040
￥38,446 total
includes taxes & fees
Oct 6 - Oct 7
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Cozy Mountain Cottage - Perfect for Friends, Family
Exterior

Cozy Mountain Cottage - Perfect for Friends, Family

10.0 out of 10, Exceptional, (15)
"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
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, (23)
"I highly recommend this cabin stay! It has absolutely everything you could need. Super clean and in a great area. Will definitely stay again if we get the chance."
The price is ￥34,988
￥78,247 total
includes taxes & fees
Oct 26 - Oct 27
Woodsy Retreat with a Hot Tub and Seasonal Views!
RIVERKEEPER INN, Waterfront Property on the Potomac River
Terrace/patio

RIVERKEEPER INN, Waterfront Property on the Potomac River

9.4 out of 10, Exceptional, (128)
"Beautiful location right on the Potomac River."
RIVERKEEPER INN, Waterfront Property on the Potomac River
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, (18)
"Very nice property with convenient location! Within walking distance of down town. "
The price is ￥24,257
￥44,708 total
includes taxes & fees
Nov 2 - Nov 3
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
4BR Cottage: Pool, Near Downtown, Heated Spa-Open Year Round, On-site Masseuse!
Exterior

4BR Cottage: Pool, Near Downtown, Heated Spa-Open Year Round, On-site Masseuse!

10.0 out of 10, Exceptional, (143)
"We will be back! The guest house was perfect for us! "
4BR Cottage: Pool, Near Downtown, Heated Spa-Open Year Round, On-site Masseuse!
C&O Canal Potomac River Cottage
Exterior

C&O Canal Potomac River Cottage

10.0 out of 10, Exceptional, (53)
"We loved this incredible location just off of dam number 4. There is beautiful hiking along the river within a stone’s throw of the porch and the house itself is like a grandmother’s hug."
C&O Canal Potomac River Cottage
Lake View Retreat - Cottage Near a Peaceful Lake!
Property grounds

Lake View Retreat - Cottage Near a Peaceful Lake!

9.6 out of 10, Exceptional, (21)
"Was really able to relax and enjoy during our brief stay. Would come again."
The price is ￥14,701
￥53,323 total
includes taxes & fees
Oct 14 - Oct 15
Lake View Retreat - Cottage Near a Peaceful Lake!
Cozy Stone Cottage in Round Hill, VA
Exterior

Cozy Stone Cottage in Round Hill, VA

9.6 out of 10, Exceptional, (9)
"Really enjoyed our stay! Would recommend for sure "
Cozy Stone Cottage in Round Hill, VA
Modern Country Cottage in Wine Country
Exterior

Modern Country Cottage in Wine Country

8.6 out of 10, Excellent, (4)
"Description of property was accurate. It worked well for our purpose. Location was.close to Leesburg and easy to get to. Mice"
Modern Country Cottage in Wine Country
Bring Your Own Boat - Meticulously restored house on the Potomac River
Exterior

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

10.0 out of 10, Exceptional, (7)
"The property was charming, clean, and easy to access. It made my stay at Fort Fredrick State Park for the Market Fair very cost-effective, with clean, private accommodations to come home to at night. Well worth the price!"
The price is ￥11,026
￥23,698 total
includes taxes & fees
Nov 1 - Nov 2
Bring Your Own Boat - Meticulously restored house on the Potomac River
The Carriage House at Carrot Top Cottage
1 bedroom, WiFi, bed sheets

The Carriage House at Carrot Top Cottage

9.8 out of 10, Exceptional, (41)
"We enjoyed the stay and it was an easy walk to the places we wanted to go!"
The price is ￥15,436
￥26,197 total
includes taxes & fees
Oct 21 - Oct 22
The Carriage House at Carrot Top 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Shepherdstown Hotel Reviews

Country Inn & Suites by Radisson, Hagerstown, MD

Country Inn & Suites by Radisson, Hagerstown, MD

10/10 Excellent
"Just stayed a couple of hours due to a last minute flight cancellation. Enjoyed the room and breakfast, the short time we were there. "
Jeff 1-night trip
Posted 2 days ago
Country Inn & Suites by Radisson, Hagerstown, MD

Find out more about Shepherdstown

Find out more about Shepherdstown

Shepherdstown Cottages information

Number of reviews
603
Accommodation
83 Cottages
Lowest Price
￥23,698
Highest Price
￥78,247

Frequently asked questions

How much do cottages in Shepherdstown cost?
Cottages in Shepherdstown range between ￥23,698 and ￥78,247 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia