Shepherdstown Rentals

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39 Houses

(6) Excellent 

21

Beautiful 1815 Stone House, private river area

West Virginia / Shepherdstown

Shepherdstown house

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$114

Price per night from

$114

17

Two-Story Charmer In Downtown Shepherdstown

West Virginia / Shepherdstown

Shepherdstown house

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Child Friendly

Price per night from

$212

Price per night from

$212

Great rentals within 20 miles that match your search

Distance approx 11.26 km from Shepherdstown

27

Family-Friendly Home on Fairway near Harpers Ferry

West Virginia / Charles Town

Charles Town house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$269

Responds fast!
avg. 58 minutes

Price per night from

$269

Distance approx 5.47 km from Shepherdstown Show on Map

(19) Very Good 

Certificate of Excellence

27

RIVERKEEPER INN, Waterfront Cottage on the Potomac

West Virginia / Harpers Ferry

Harpers Ferry bungalow

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Certificate of Excellence

Price per night from

$137

Responds fast!
avg. 52 minutes

Price per night from

$137

Distance approx 7.93 km from Shepherdstown Show on Map

(2) Excellent 

6

Marbrun House in Historic Harpers Ferry

West Virginia / Harpers Ferry

Harpers Ferry room

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Air conditioning
  • Private garden

Price per night from

$86

Responds fast!
avg. 1 hour 45 minutes

Price per night from

$86

Distance approx 8.23 km from Shepherdstown Show on Map

24

Harpers Ferry Apt. w/ Pool, Hot Tub & Tiki Bar!

West Virginia / Harpers Ferry

Harpers Ferry apartment

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Air conditioning

Price per night from

$130

Responds fast!
avg. 10 minutes

Price per night from

$130

Distance approx 10.25 km from Shepherdstown

15

Private and Remodeled Historic 2 Bedroom Condo in Heart of Downtown Charles Town

West Virginia / Charles Town

Charles Town apartment

2 5 1 night min

  • 2 bedrooms
  • sleeps 5
  • 1 night min
  • Child Friendly
  • Air conditioning

Price per night from

$114

Price per night from

$114

Distance approx 5.87 km from Shepherdstown Show on Map

(3) Very Good 

12

Antietam Creek 2 bedroom cabin

Maryland / Keedysville

Keedysville house

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Swimming pool
  • Child Friendly
  • Private garden

Price per night from

$172

Price per night from

$172

Distance approx 8.09 km from Shepherdstown Show on Map

(15) Excellent 

38

Adventure Inn - Historic Home with Hot Tub, close

West Virginia / Harpers Ferry

Harpers Ferry house

4 14 2 nights min

  • 4 bedrooms
  • sleeps 14
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Ask about pets
“Quaint and convenient” A great little vacation rental that can be teamed up with a River Rider's adventure when the season changes. Kids had a blast running in the big yard, and the parents had a great time enjoying the multiple fire places. It was
…see more

Price per night from

$401

Price per night from

$401

Distance approx 4.97 km from Shepherdstown Show on Map

(1) Excellent 

10

Apartment on Peace Ridge Farm

West Virginia / Harpers Ferry

Harpers Ferry apartment

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$252

Price per night from

$252

Distance approx 18.34 km from Shepherdstown

15

A Zen Mountain Retreat

West Virginia / Hedgesville

Hedgesville house

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$143

Price per night from

$143

Distance approx 17.78 km from Shepherdstown

14

The Inn At Waterford

Loudoun County / Waterford

Waterford b and b

4 8 1 night min

  • 4 bedrooms
  • sleeps 8
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$573

Price per night from

$573

Distance approx 15.8 km from Shepherdstown

15

Catoctin Valley Country Home

Loudoun County / Lovettsville

Lovettsville house

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$682

Responds fast!
avg. 2 hours 23 minutes

Price per night from

$682

Distance approx 18.4 km from Shepherdstown

28

Brookwood Chalet

West Virginia / Hedgesville

Hedgesville house

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Swimming pool
  • Air conditioning
  • Pet Friendly

Price per night from

$189

Price per night from

$189

Distance approx 17.9 km from Shepherdstown

30

Treetop Cottage

West Virginia / Hedgesville

Hedgesville house

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Swimming pool
  • Air conditioning

Price per night from

$189

Price per night from

$189

Distance approx 18.1 km from Shepherdstown

(1) Excellent 

25

Sienna Room at Loudoun Valley Manor - off Route 9 near Leesburg

Loudoun County / Waterford

Waterford b and b

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Air conditioning
  • Private garden

Price per night from

$75

Responds fast!
avg. 37 minutes

Price per night from

$75

Distance approx 18.08 km from Shepherdstown

(4) Excellent 

Certificate of Excellence

29

Golden Room at Loudoun Valley Manor near Leesburg

Loudoun County / Waterford

Waterford house

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Air conditioning
  • Private garden

Certificate of Excellence

Price per night from

$109

Responds fast!
avg. 37 minutes

Price per night from

$109

Distance approx 18.08 km from Shepherdstown

(1) Excellent 

25

Green room - suite at Loudoun Valley Manor

Loudoun County / Waterford

Waterford house

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Air conditioning
  • Private garden

Price per night from

$121

Responds fast!
avg. 37 minutes

Price per night from

$121

Distance approx 7.99 km from Shepherdstown Show on Map

(2) Excellent 

5

Gorgeous Mountain Views - Walk to historic town

West Virginia / Harpers Ferry

Harpers Ferry apartment

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Ask about pets

Price per night from

$225

Responds fast!
avg. 1 hour 11 minutes

Price per night from

$225

Distance approx 7.9 km from Shepherdstown Show on Map

(6) Very Good 

15

Two Rivers Guest House. Walk to rivers, parks, downtown and restaurants

West Virginia / Harpers Ferry

Harpers Ferry house

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$240

Price per night from

$240

Distance approx 5.62 km from Shepherdstown Show on Map

4

Compound Historic Nature Preserve

West Virginia / Kearneysville

Kearneysville tented camp

1 15 min stay varies

  • 1 bedroom
  • sleeps 15
  • min stay varies
  • Child Friendly
  • Pet Friendly

Price per night from

$25

Price per night from

$25

Distance approx 16.24 km from Shepherdstown

(11) Excellent 

19

Ruby Summit Point - Your Home at the Track

West Virginia / Summit Point

Summit Point house

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Air conditioning
  • Ask about pets
  • Private garden
“Convenience and Comfort at the Track” Ruby Summit Point is a great place to say with a group of friends over a track weekend. Very close to the track so no time wasted commuting to distant hotels. Very nicely upgraded kitchen and entire house. Beautif
…see more

Price per night from

$229

Price per night from

$229

Distance approx 18.38 km from Shepherdstown

(1) Average 

24

Wildwood Cottage

West Virginia / Hedgesville

Hedgesville house

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$154

Price per night from

$154

Distance approx 19.49 km from Shepherdstown

(1) Excellent 

18

Above Sleepy Hollow

West Virginia / Berkeley Springs

Berkeley Springs cottage

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Pet Friendly

Price per night from

$252

Price per night from

$252

Distance approx 7.88 km from Shepherdstown Show on Map

(6) Excellent 

4

Cantuta Inn Bed & Breakfast - Shallows Room 1

West Virginia / Harpers Ferry

Harpers Ferry b and b

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$149

Price per night from

$149

Distance approx 10.36 km from Shepherdstown

24

NEW! Cozy Garden-Level Apt - Walk to Charles Town!

West Virginia / Charles Town

Charles Town apartment

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$98

Responds fast!
avg. 14 minutes

Price per night from

$98

Distance approx 7.87 km from Shepherdstown Show on Map

(1) Excellent 

4

Cantuta Inn Bed & Breakfast - Shallows Room 4

West Virginia / Harpers Ferry

Harpers Ferry b and b

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$149

Price per night from

$149

Distance approx 10.25 km from Shepherdstown

12

Private One Bedroom Condo in Downtown Charles Town Above Future Microbrewery

West Virginia / Charles Town

Charles Town apartment

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Child Friendly
  • Air conditioning

Price per night from

$114

Price per night from

$114

Distance approx 8.07 km from Shepherdstown Show on Map

4

Cantuta Inn Bed & Breakfast - Shallows Room 2

West Virginia / Harpers Ferry

Harpers Ferry b and b

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$130

Price per night from

$130

Distance approx 7.87 km from Shepherdstown Show on Map

4

Cantuta Inn Bed & Breakfast - Shallows Room 3

West Virginia / Harpers Ferry

Harpers Ferry b and b

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$149

Price per night from

$149

Distance approx 18.08 km from Shepherdstown

18

Burgundy room - Loudoun Valley Manor

Loudoun County / Waterford

Waterford b and b

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Air conditioning
  • Private garden

Price per night from

$95

Responds fast!
avg. 37 minutes

Price per night from

$95

Distance approx 6.35 km from Shepherdstown Show on Map

(1) Excellent 

11

Rose Cottage Bed and Breakfast

Maryland / Fairplay

Fairplay b and b

2 2 1 night min

  • 2 bedrooms
  • sleeps 2
  • 1 night min
  • Air conditioning
  • Private garden

Price per night from

$172

Price per night from

$172

Distance approx 17.88 km from Shepherdstown

16

Wood Song

West Virginia / Hedgesville

Hedgesville house

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Pet Friendly

Price per night from

$234

Price per night from

$234

Distance approx 18.8 km from Shepherdstown

32

Starry Nights

West Virginia / Hedgesville

Hedgesville house

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min

Price per night from

$176

Price per night from

$176

Distance approx 18.51 km from Shepherdstown

22

Country Comfort

West Virginia / Hedgesville

Hedgesville house

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min

Price per night from

$149

Price per night from

$149

Distance approx 17.94 km from Shepherdstown

(2) Average 

36

Fox Hollow

West Virginia / Hedgesville

Hedgesville house

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min

Price per night from

$260

Price per night from

$260

Distance approx 18.47 km from Shepherdstown

(1) Excellent 

12

The Wander Inn

Maryland / Frederick

Frederick apartment

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Air conditioning
  • Pet Friendly
  • Private garden

Price per night from

$109

Price per night from

$109

Distance approx 18.92 km from Shepherdstown

26

Grove Guest Home

Maryland / Frederick

Frederick house

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$195

Price per night from

$195