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Check prices for these dates

In two weeks
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec

Browse Select Shepherdstown Cottages

Historic Boonsboro Vacation Rental w/ Grill
House (2 Bedrooms) | Interior

Historic Boonsboro Vacation Rental w/ Grill

3.0 star property
Historic Boonsboro Vacation Rental w/ Grill
Charming Home With Yard Near Shenandoah River!
House (3 Bedrooms) | Interior

Charming Home With Yard Near Shenandoah River!

3.0 star property
10.0 out of 10, Exceptional, (3)
"Cozy house nestled in the mountains of West Virginia. Well-maintained, clean, great yard for pets and/or kids! Lovely grilling and fire pit area. We throughly enjoyed our stay!"
Charming Home With Yard Near Shenandoah River!
Walk to Stores: Home in Historic Shepherdstown!
House (3 Bedrooms) | Interior

Walk to Stores: Home in Historic Shepherdstown!

3.0 star property
Walk to Stores: Home in Historic Shepherdstown!
Renovated WV Schoolhouse: History Buffs Heaven!
House (1 Bedroom) | Interior

Renovated WV Schoolhouse: History Buffs Heaven!

3.0 star property
10.0 out of 10, Exceptional, (2)
"The school house is amazing. Clean, comfortable, quiet. I would definitely stay there again if I am in the area"
Renovated WV Schoolhouse: History Buffs Heaven!
Spacious Mercersburg Home at Whitetail Resort
House (4 Bedrooms) | Front of property

Spacious Mercersburg Home at Whitetail Resort

3.0 star property
Spacious Mercersburg Home at Whitetail Resort
Charming Hedgesville Retreat w/ Deck + Fireplace!
House (2 Bedrooms) | Interior

Charming Hedgesville Retreat w/ Deck + Fireplace!

3.0 star property
10.0 out of 10, Exceptional, (3)
Charming Hedgesville Retreat w/ Deck + Fireplace!
Creekside Berkeley Springs Cabin on 35 Acres!
House (3 Bedrooms) | Interior

Creekside Berkeley Springs Cabin on 35 Acres!

3.0 star property
"The cabin was immaculately clean and comfortable! We had so much space for our party of five to spread out and enjoy ourselves. The beds were very comfy, and the full, updated kitchen was so useful during our stay as we were in the area for a reunion. We loved the outdoor area, too, and enjoyed spending time talking around the firepit. The homeowners even provided the marshmallows, graham crackers and chocolate to make s'mores, which we did! It was a wonderful stay, and we're already talking...
Creekside Berkeley Springs Cabin on 35 Acres!
Couples Cabin - 5 Mi to DT Berkeley Springs!
House (1 Bedroom) | Interior

Couples Cabin - 5 Mi to DT Berkeley Springs!

3.0 star property
8.0 out of 10, Very good, (1)
"The people were super friendly... the place is very nice. "
Couples Cabin - 5 Mi to DT Berkeley Springs!
Spacious Virginia Vacation Rental w/ Yard & Sauna
House (4 Bedrooms) | Interior

Spacious Virginia Vacation Rental w/ Yard & Sauna

3.0 star property
Spacious Virginia Vacation Rental w/ Yard & Sauna
Harpers Ferry Cabin - Walk to Private Lake!
House (3 Bedrooms) | Front of property

Harpers Ferry Cabin - Walk to Private Lake!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Great property, and really excellent communication when we had questions."
Harpers Ferry Cabin - Walk to Private Lake!
Lovettsville Cottage in Heart of Wine Country
Cottage (1 Bedroom) | Interior

Lovettsville Cottage in Heart of Wine Country

3.0 star property
Lovettsville Cottage in Heart of Wine Country
West Virginia Home w/ Deck on Golf Course
House (4 Bedrooms) | Interior

West Virginia Home w/ Deck on Golf Course

3.0 star property
West Virginia Home w/ Deck on Golf Course
Private Mountain Home Near Shenandoah River!
Exterior

Private Mountain Home Near Shenandoah River!

3.0 star property
Private Mountain Home Near Shenandoah River!
Peaceful & Secluded Knoxville Retreat w/ Deck
Terrace/patio

Peaceful & Secluded Knoxville Retreat w/ Deck

3.0 star property
10.0 out of 10, Exceptional, (1)
"loved this property, secluded, quiet. Had everything we needed, coffee makers, utensils, washer/dryer, outdoor fire pit, to name a few. a couple of miles of the main road, but very scenic. Only negative, (and wasn't really a negative), the road to Harpers Ferry was out, had to use detour, and extra 20 minute drive, but was a beautiful detour drive!"
Peaceful & Secluded Knoxville Retreat w/ Deck
Waterfront Cabin on 32 Acres in Leesburg!
Cottage (4 Bedrooms) | Interior

Waterfront Cabin on 32 Acres in Leesburg!

3.0 star property
Waterfront Cabin on 32 Acres in Leesburg!
Hike, Sip & Explore: Charming Waterford Cottage!
Cottage (1 Bedroom) | Interior

Hike, Sip & Explore: Charming Waterford Cottage!

3.0 star property
Hike, Sip & Explore: Charming Waterford Cottage!
Pet-friendly Berryville Home: Walk to Main Street!
House (3 Bedrooms) | Interior

Pet-friendly Berryville Home: Walk to Main Street!

3.0 star property
Pet-friendly Berryville Home: Walk to Main Street!
Large Family Home: 5 Mi to Dtwn Hagerstown!
House (3 Bedrooms) | Interior

Large Family Home: 5 Mi to Dtwn Hagerstown!

3.0 star property
Large Family Home: 5 Mi to Dtwn Hagerstown!
Historic Jefferson Farmhouse - Hike, Bike & Raft!
House (5 Bedrooms) | Interior

Historic Jefferson Farmhouse - Hike, Bike & Raft!

3.0 star property
Historic Jefferson Farmhouse - Hike, Bike & Raft!
Huge Hagerstown Home w/ Deck ~ 4 Mi to Downtown!
House (3 Bedrooms) | Interior

Huge Hagerstown Home w/ Deck ~ 4 Mi to Downtown!

3.0 star property
Huge Hagerstown Home w/ Deck ~ 4 Mi to Downtown!
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

Holiday Inn Express Charles Town by IHG

Holiday Inn Express Charles Town by IHG

10/10 Excellent
"The hotel is very clean and comfortable. The breakfast is good and the shuttle service is very convenient and was a nice surprise (they'll take you anywhere within 2 miles and pick you up). The staff was all very nice and helpful. "
Melissa 2-night trip
Posted 6 days ago
Holiday Inn Express Charles Town by IHG

Find out more about Shepherdstown

Find out more about Shepherdstown

Shepherdstown Cottages information

Number of reviews
7
Accommodation
39 Cottages
Lowest Price
Highest Price

Frequently asked questions

How much do cottages in Shepherdstown cost?
Cottages in Shepherdstown range between and 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 holiday 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.

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