Shepherdstown, WV Vacation Homes from AED 958

Shepherdstown Vacation Homes
West Virginia
United States of America
Expedia.ae

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

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Shepherdstown vacation homes

A kitchen with wooden cabinets, a stainless steel refrigerator, and a microwave.

A window with a view of a grassy yard and trees.

A brick house with a front porch, a small garden, and a tree in the foreground.

A two-story brick house with a front porch, a small garden, and a visible mailbox.

1. Charming Shepherdstown Home - Walk to Downtown

Charming Shepherdstown Home - Walk to Downtown

Shepherdstown

The price is AED 591

AED 591

AED 1,148 total

includes taxes & fees

18 Oct - 19 Oct

Charming Shepherdstown Home - Walk to Downtown

A nighttime forest path lit by string lights.

A casino with slot machines, red chairs, and a colorful carpet.

A dining area with a round wooden table, black chairs, a chandelier, and a view through a sliding glass door to a deck.

A glass of red wine with a label, a fire pit, and two Adirondack chairs in a natural setting.

2. 1-Acre Hot Tub & Fire Pit Retreat, Steps to Winery and Battlefield

1-Acre Hot Tub & Fire Pit Retreat, Steps to Winery and Battlefield

Sharpsburg

10.0 out of 10, Exceptional, (54 reviews)

10/10

Exceptional

(54 reviews)

"The house was in a great location with the winery and battlefield nearby, and the house was very nice and comfortable."

Nancy D.

1-Acre Hot Tub & Fire Pit Retreat, Steps to Winery and Battlefield

A deck with green chairs and a fire pit, surrounded by a house and trees.

A modern kitchen with grey cabinets, a large island with bar stools, stainless steel appliances, and pendant lighting.

A two-story blue house with a front porch, a small attached garage, and a gravel driveway.

A cozy living room with a stone fireplace, a comfortable wooden chair, and a large window.

3. 4 King Suites, Hot Tub, Ping Pong, Arcade, Chef's Kitchen – Harpers Ferry

4 King Suites, Hot Tub, Ping Pong, Arcade, Chef's Kitchen – Harpers Ferry

Knoxville

10.0 out of 10, Exceptional, (32 reviews)

10/10

Exceptional

(32 reviews)

"Great stay, super nice people and wonderful house."

Kenzie S.

The price is AED 569

AED 569

AED 1,869 total

includes taxes & fees

18 Oct - 19 Oct

4 King Suites, Hot Tub, Ping Pong, Arcade, Chef's Kitchen – Harpers Ferry

A house with a well-lit entrance, a small garden, and a gravel driveway.

A dining area with a table set for two, a clock on the wall, and a blue door with a window.

A modern kitchen with stainless steel appliances, a window with a view of trees, and a blue countertop.

A dark entrance with a lit door, two windows on either side, and a bell on the right.

4. Custom Train-Themed Lodge on 7 Private Acres with Walking Trails

Custom Train-Themed Lodge on 7 Private Acres with Walking Trails

Martinsburg

9.8 out of 10, Exceptional, (24 reviews)

9.8/10

Exceptional

(24 reviews)

"Nice place to stay. Could use some privacy."

Arnold A.

The price is AED 314

AED 314

AED 958 total

includes taxes & fees

20 Oct - 21 Oct

Custom Train-Themed Lodge on 7 Private Acres with Walking Trails

An outdoor patio with a wooden deck, a hanging chair, a cushioned sofa, and various potted plants.

A modern kitchen with white cabinets, a wooden countertop, and a sliding glass door leading to an outdoor seating area.

A modern living room with a white sofa, a wooden coffee table, and a large grey door.

A modern living room with a large flat-screen TV mounted on the wall, a sofa, a coffee table, and a side table with a lamp.

5. New AC. Luxury, Spa Bathroom, Movie Room, high-end design, fall colors Oct

New AC. Luxury, Spa Bathroom, Movie Room, high-end design, fall colors Oct

Bolivar

9.8 out of 10, Exceptional, (50 reviews)

9.8/10

Exceptional

(50 reviews)

"Great location and incredibly well appointed!"

Sarah M.

The price is AED 493

AED 493

AED 1,068 total

includes taxes & fees

18 Oct - 19 Oct

New AC. Luxury, Spa Bathroom, Movie Room, high-end design, fall colors Oct

KITCHEN/LIVING ROOM - 2nd floor long view showing the whole space, tv, wifi

ENTRANCE - front walk made of brick, lovely landscaping. Keyless entry.

DINING ROOM - 2nd floor dining room easily fits 6, spare chairs, stairs backyard

HOUSE - brick walks, landscaped, deck on 2nd floor, patio below. Keyless entry.

6. Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront

Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront

Sharpsburg

8.2 out of 10, Very good, (66 reviews)

8.2/10

Very good

(66 reviews)

"Lovely place along the c&o. The host was very accommodating and helpful."

Laura D.

The price is AED 757

AED 757

AED 1,675 total

includes taxes & fees

5 Nov - 6 Nov

Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront

A spacious living area with two grey sofas, a wooden floor, and a kitchen in the background.

A modern kitchen with a central island, bar stools, a ceiling fan, pendant lights, a large flat-screen TV, wooden cabinetry, and a patterned rug.

A kitchen with granite countertops, stainless steel appliances, and blue pendant lights.

A snowy forest scene with a wooden deck in the foreground.

7. Hidden Creekside retreat near 5 national parks, including Harpers Ferry

Hidden Creekside retreat near 5 national parks, including Harpers Ferry

Martinsburg

9.8 out of 10, Exceptional, (10 reviews)

9.8/10

Exceptional

(10 reviews)

"Wonderful location and property."

Helen F.

The price is AED 459

AED 459

AED 1,129 total

includes taxes & fees

13 Nov - 14 Nov

Hidden Creekside retreat near 5 national parks, including Harpers Ferry

A bedroom with a bed, a chair, a nightstand, a ceiling fan, and a window with curtains.

A kitchen with white cabinets, a black refrigerator, a wooden table, and a ceiling fan.

A bathroom with a toilet, sink, and shower curtain.

A spacious living room with a large window, a wooden coffee table, and a sofa.

8. Schilling House

Schilling House

3.0 star property

Bolivar

The price is AED 946

AED 946

AED 1,196 total

includes taxes & fees

3 Nov - 4 Nov

Schilling House

A two-story house with a porch, green shutters, and a red roof.

A kitchen with a wooden table, two windows, and a stove.

A porch with a bench, a red rug, and a door with a sign reading "Private Home Welcome".

A cozy living room with striped sofas, a television, and artwork on the walls.

9. Enchanting Cottage, walk to Downtown Harpers Ferry

Enchanting Cottage, walk to Downtown Harpers Ferry

Harpers Ferry

9.6 out of 10, Exceptional, (58 reviews)

9.6/10

Exceptional

(58 reviews)

"Great place in historic Harper’s ferry. Only negative thing I can say is the parking is not ideal"

Brett D.

The price is AED 780

AED 780

AED 1,455 total

includes taxes & fees

28 Oct - 29 Oct

Enchanting Cottage, walk to Downtown Harpers Ferry

An outdoor patio with wooden flooring, two white cushioned chairs, and a small table.

A modern kitchen with a wooden dining table, clear chairs, and a pendant light.

A bedroom with a wooden headboard, a TV mounted on the wall, a bed with a blue floral bedspread, and a wooden floor.

A modern living room with a sofa, coffee table, and dining table. There is a kitchen area with a counter and shelves.

10. Icy mini split added, luxury, walk to Washington St, EV, Movie room, Spa bath

Icy mini split added, luxury, walk to Washington St, EV, Movie room, Spa bath

Bolivar

10.0 out of 10, Exceptional, (62 reviews)

10/10

Exceptional

(62 reviews)

"Enjoyed our stay here. Host was very communicative and the place was very clean."

Delaine F.

The price is AED 547

AED 547

AED 1,126 total

includes taxes & fees

21 Oct - 22 Oct

Icy mini split added, luxury, walk to Washington St, EV, Movie room, Spa bath

A square fire pit with a brick base, surrounded by outdoor furniture including a sofa and chairs.

A cozy attic bedroom with a skylight, a wicker chair, a round table, and a bed with a headboard.

A wooden door with a sign above it reading 'The Robin's Nest.'

A teal chair at a white desk with a notebook, pen, and mug.

11. Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit

Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit

Boonsboro

9.8 out of 10, Exceptional, (18 reviews)

9.8/10

Exceptional

(18 reviews)

"Extremely cute and a wonderful place to relax."

A D.

The price is AED 550

AED 550

AED 1,227 total

includes taxes & fees

18 Oct - 19 Oct

Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit

A four-poster canopy bed with a view of a cityscape through the window.

A modern kitchen with a central island, built-in appliances, and a decorative neon sign.

An outdoor patio with a wooden deck, a table, and four Adirondack chairs.

A modern dining area with a round table and clear chairs, a potted plant, and a neon art piece on the wall.

12. Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry

Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry

Harpers Ferry

10.0 out of 10, Exceptional, (21 reviews)

10/10

Exceptional

(21 reviews)

"Great spot"

Clara

The price is AED 661

AED 661

AED 1,141 total

includes taxes & fees

30 Oct - 31 Oct

Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry

A modern kitchen with wooden cabinets, a large island with stools, and a bar area.

A spacious living room with hardwood flooring, two dark armchairs, a round ottoman, a floor lamp, and large windows with white curtains.

A living room with a fireplace, a television, and a dining area with a table and chairs.

A two-story house with a green exterior, a red door, and a porch with steps leading to the front door.

13. Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC

Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC

Rohrersville

10.0 out of 10, Exceptional, (19 reviews)

10/10

Exceptional

(19 reviews)

"Beautiful house in a bucolic setting. Perfect for a family for the night."

Kate M.

The price is AED 1,010

AED 1,010

AED 1,659 total

includes taxes & fees

29 Oct - 30 Oct

Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC

A living room with two dark sofas, a wooden coffee table, and a chandelier.

A wooden deck with a table and chairs, a grill, and a pergola with an umbrella.

A bedroom with a bed, a nightstand, a dresser, a ceiling fan, and a window.

A hallway with a wooden floor, white trim, and a door on the left.

14. Cozy Getaway Near History, Hiking & Adventure

Cozy Getaway Near History, Hiking & Adventure

Bolivar

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"This house was perfect for our getaway. Clean and comfortable. Close to everything."

Ashlee O.

Cozy Getaway Near History, Hiking & Adventure

A modern kitchen with a central island, stainless steel appliances, and a stone accent wall.

A spacious kitchen with a large island, wooden flooring, and a stone fireplace.

A covered outdoor deck with a sofa, chairs, and a fire pit.

A kitchen with white cabinetry, a marble countertop, and a window overlooking a deck.

15. Brand new home in Historic Harpers Ferry - Barrel Sauna - Fire Pit - Luxury!

Brand new home in Historic Harpers Ferry - Barrel Sauna - Fire Pit - Luxury!

Harpers Ferry

10.0 out of 10, Exceptional, (15 reviews)

10/10

Exceptional

(15 reviews)

"Beautiful home. Very attentive hosts, great location. We enjoyed every minute at this home. "

Katrina

The price is AED 776

AED 776

AED 1,728 total

includes taxes & fees

9 Nov - 10 Nov

Brand new home in Historic Harpers Ferry - Barrel Sauna - Fire Pit - Luxury!

A hammock on a grassy area with a view of a river and forested hills.

A two-story house with a covered porch and a stone pathway leading to the entrance.

A spacious kitchen with large windows, a built-in bench, and a view of the outside.

A spacious kitchen with a central island, wooden beams, and a large window.

16. La Soledad Lavender Farm on the Potomac

La Soledad Lavender Farm on the Potomac

Harpers Ferry

10.0 out of 10, Exceptional, (32 reviews)

10/10

Exceptional

(32 reviews)

"Terrific place and very friendly and accommodating host"

Michel R.

The price is AED 1,102

AED 1,102

AED 1,583 total

includes taxes & fees

11 Nov - 12 Nov

La Soledad Lavender Farm on the Potomac

A wooden staircase with a handrail, a chandelier, and a patterned rug on the floor.

A dining room with a round table, wooden chairs, a chandelier, and a china cabinet.

A spacious living room with hardwood flooring, a fireplace, and a green sofa.

A room with a wooden floor, a chair, a large window, and a door.

17. Historic Queen Anne Family Home w Modern Comforts

Historic Queen Anne Family Home w Modern Comforts

Harpers Ferry

9.2 out of 10, Wonderful, (9 reviews)

9.2/10

Wonderful

(9 reviews)

"This was a wonderful vacation rental--clean, beautifully appointed, and located within walking distance of historic Harpers Ferry and the AT. We couldn't have asked for a nicer place to spend our long weekend getaway."

Jenny H.

Historic Queen Anne Family Home w Modern Comforts

A staircase with white steps and a wooden handrail, leading to a dining area with a table and chairs.

A bedroom with a bed, a dresser, a nightstand, a fireplace, and a hallway.

A loft-style room with a wooden floor, a sofa, a woven ottoman, a staircase, and a railing.

A living room with a dark blue wall, a wooden coffee table, a blue sofa, and a chandelier.

18. The Retreat at Harpers Ferry

The Retreat at Harpers Ferry

Bolivar

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"Wonderful stay. House was lovely. Back yard / gazebo fabulous for hanging out. Everything you needed in home from the stocked coffee bar down to Q-tips. Within walking distance to some interesting entertainment & cafes. Very pleasant stay. Will do again."

Tonia Y.

The Retreat at Harpers Ferry

A dining area with a glass table surrounded by chairs, a living room in the background, and a window with white curtains.

A spacious living area with a dark blue sofa, wooden coffee table, and a staircase leading to another level.

A two-story house with a front porch, a staircase leading to the entrance, and a garden with various plants and flowers.

An outdoor patio with wooden deck, stone tiles, and red chairs.

19. Charming 3-Bedroom Home in historic Harpers Ferry: Pet Friendly!

Charming 3-Bedroom Home in historic Harpers Ferry: Pet Friendly!

Harpers Ferry

10.0 out of 10, Exceptional, (46 reviews)

10/10

Exceptional

(46 reviews)

"The house was wonderful with everything you would need for a stay. It was located perfectly for walking in town. We could not be happier with our accommodations. Great house, great location, great experience. Highly recommended."

JANELLE G.

The price is AED 1,062

AED 1,062

AED 1,788 total

includes taxes & fees

29 Oct - 30 Oct

Charming 3-Bedroom Home in historic Harpers Ferry: Pet Friendly!

A wooden deck with a view of a forested landscape and a sunset.

An aerial view of a house surrounded by dense forest, with a clear sky above.

A kitchen with wooden cabinets, a dining table with chairs, a TV, and a ceiling fan.

A living room with a wooden floor, a sofa, a coffee table with board games, books, and a gaming console. There is a TV and speakers in the background.

20. A peaceful, forest retreat with stunning views near historic Harpers Ferry.

A peaceful, forest retreat with stunning views near historic Harpers Ferry.

Harpers Ferry

9.0 out of 10, Wonderful, (15 reviews)

9.0/10

Wonderful

(15 reviews)

"House was clean and loaded with required amenities. We loved the backyard view and the proximity to the lakeside picnic area."

henu m.

The price is AED 661

AED 661

AED 1,418 total

includes taxes & fees

21 Oct - 22 Oct

A peaceful, forest retreat with stunning views near historic Harpers Ferry.

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

Find vacation rentals that suit your style

Cabins

search for cabins

Apartments

search for apartments

Villas

search for villas

Private vacation homes

search for private vacation homes

Condos

search for condos

Cottages

search for cottages

Chalets

search for chalets

Save an average of 15% on thousands of hotels when you're signed in

Top Shepherdstown Hotel Reviews

Quality Inn Harpers Ferry - Charles Town

10/10 Excellent

"Comfy beds and a great location with just a short drive everywhere!"

Bethany 1-night trip

Posted 1 hour ago

Quality Inn Harpers Ferry - Charles Town

Mirror Villas - Modern Retreat with private hot tubs and mountain view

10/10 Excellent

"Excellent"

Kevin 2-night trip

Posted 4 hours ago

Mirror Villas - Modern Retreat with private hot tubs and mountain view

Clarion Inn Harpers Ferry - Charles Town

8/10 Good

"Rooms are older but staff was very nice and helpful with check in"

Kathleen 2-night trip

Posted 7 hours ago

Clarion Inn Harpers Ferry - Charles Town

Quality Inn Shepherdstown

10/10 Excellent

"Great"

Terry 1-night trip

Posted 1 day ago

Quality Inn Shepherdstown

Days Inn by Wyndham Frederick

8/10 Good

"Due to old age and limited mobility, I need to choose hotels where I can park right at the door to the room, like this Days Inn. The room was clean, the bed was comfortable, and the surroundings were very quiet. It is a budget property, so don't check in expecting luxury."

robert 1-night trip

Posted 1 day ago

Days Inn by Wyndham Frederick

Hampton Inn & Suites Frederick-Fort Detrick

10/10 Excellent

"Good"

Hope 1-night trip

Posted 1 day ago

Hampton Inn & Suites Frederick-Fort Detrick

Country Inn & Suites by Radisson, Frederick, MD

10/10 Excellent

"Rooms and services were the equivalent of much higher priced hotels."

Jerry 1-night trip

Posted 1 day ago

Country Inn & Suites by Radisson, Frederick, MD

Country Inn & Suites by Radisson, Hagerstown, MD

10/10 Excellent

"Great stay!"

Dennis 6-night trip

Posted 2 days ago

Country Inn & Suites by Radisson, Hagerstown, MD

Comfort Inn Frederick - Ballenger Creek

10/10 Excellent

"Excellent room and breakfast"

Charles 1-night trip

Posted 2 days ago

Comfort Inn Frederick - Ballenger Creek

Search Vacation Homes in Shepherdstown

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Shepherdstown vacation homes

1. Charming Shepherdstown Home - Walk to Downtown

2. 1-Acre Hot Tub & Fire Pit Retreat, Steps to Winery and Battlefield

3. 4 King Suites, Hot Tub, Ping Pong, Arcade, Chef's Kitchen – Harpers Ferry

4. Custom Train-Themed Lodge on 7 Private Acres with Walking Trails

5. New AC. Luxury, Spa Bathroom, Movie Room, high-end design, fall colors Oct

6. Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront

7. Hidden Creekside retreat near 5 national parks, including Harpers Ferry

8. Schilling House

9. Enchanting Cottage, walk to Downtown Harpers Ferry

10. Icy mini split added, luxury, walk to Washington St, EV, Movie room, Spa bath

11. Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit

12. Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry

13. Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC

14. Cozy Getaway Near History, Hiking & Adventure

15. Brand new home in Historic Harpers Ferry - Barrel Sauna - Fire Pit - Luxury!

16. La Soledad Lavender Farm on the Potomac

17. Historic Queen Anne Family Home w Modern Comforts

18. The Retreat at Harpers Ferry

19. Charming 3-Bedroom Home in historic Harpers Ferry: Pet Friendly!

20. A peaceful, forest retreat with stunning views near historic Harpers Ferry.

Find vacation rentals that suit your style

Top Shepherdstown Hotel Reviews

Quality Inn Harpers Ferry - Charles Town