Shepherdstown Rentals

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58 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

    Responds fast!
    avg. 22 minutes

    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 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 39 minutes

          Price per night from

          $86

          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 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 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

                $86

                Responds fast!
                avg. 26 minutes

                Price per night from

                $86

                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. 26 minutes

                  Price per night from

                  $121

                  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. 26 minutes

                    Price per night from

                    $109

                    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 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 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

                          $258

                          Responds fast!
                          avg. 1 hour 11 minutes

                          Price per night from

                          $258

                          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 7.9 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

                              $275

                              Price per night from

                              $275

                              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

                                $177

                                Price per night from

                                $177

                                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 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. 11 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 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

                                            $109

                                            Responds fast!
                                            avg. 26 minutes

                                            Price per night from

                                            $109

                                            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 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

                                                $149

                                                Price per night from

                                                $149

                                                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 7.86 km from Shepherdstown Show on Map

                                                    7

                                                    Light Horse Inn: Suite 2

                                                    West Virginia / Harpers Ferry

                                                    Harpers Ferry house

                                                    1 2 min stay varies

                                                    • 1 bedroom
                                                    • sleeps 2
                                                    • min stay varies
                                                    • Ask about children
                                                    • Air conditioning

                                                    Price per night from

                                                    $184

                                                    Price per night from

                                                    $184

                                                    Distance approx 8.08 km from Shepherdstown Show on Map

                                                      12

                                                      Country Cottage with Super Location All Private Suite & Breakfast Included

                                                      West Virginia / Harpers Ferry

                                                      Harpers Ferry apartment

                                                      2 5 2 nights min

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

                                                      Price per night from

                                                      $149

                                                      Price per night from

                                                      $149

                                                      Distance approx 7.86 km from Shepherdstown Show on Map

                                                        8

                                                        Light Horse Inn: Suite 6

                                                        West Virginia / Bolivar

                                                        Bolivar house

                                                        1 2 min stay varies

                                                        • 1 bedroom
                                                        • sleeps 2
                                                        • min stay varies
                                                        • Ask about children
                                                        • Air conditioning

                                                        Price per night from

                                                        $184

                                                        Price per night from

                                                        $184

                                                        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 7.86 km from Shepherdstown Show on Map

                                                            9

                                                            Light Horse Inn: Suite 5

                                                            West Virginia / Bolivar

                                                            Bolivar house

                                                            1 2 min stay varies

                                                            • 1 bedroom
                                                            • sleeps 2
                                                            • min stay varies
                                                            • Ask about children
                                                            • Air conditioning

                                                            Price per night from

                                                            $184

                                                            Price per night from

                                                            $184

                                                            Distance approx 8.23 km from Shepherdstown Show on Map

                                                              8

                                                              Ledge House B&B: Suite 1

                                                              West Virginia / Harpers Ferry

                                                              Harpers Ferry house

                                                              1 2 min stay varies

                                                              • 1 bedroom
                                                              • sleeps 2
                                                              • min stay varies
                                                              • Ask about children
                                                              • Air conditioning

                                                              Price per night from

                                                              $195

                                                              Price per night from

                                                              $195

                                                              Distance approx 7.85 km from Shepherdstown Show on Map

                                                                12

                                                                Vacation Rental: Merchants Flat

                                                                West Virginia / Bolivar

                                                                Bolivar apartment

                                                                2 4 min stay varies

                                                                • 2 bedrooms
                                                                • sleeps 4
                                                                • min stay varies
                                                                • Ask about children
                                                                • Pet Friendly

                                                                Price per night from

                                                                $201

                                                                Price per night from

                                                                $201

                                                                Distance approx 7.86 km from Shepherdstown Show on Map

                                                                  8

                                                                  Vacation Rental: Armory Quarters A

                                                                  West Virginia / Harpers Ferry

                                                                  Harpers Ferry cottage

                                                                  1 2 min stay varies

                                                                  • 1 bedroom
                                                                  • sleeps 2
                                                                  • min stay varies
                                                                  • Ask about children
                                                                  • Air conditioning
                                                                  • Pet Friendly

                                                                  Price per night from

                                                                  $149

                                                                  Price per night from

                                                                  $149

                                                                  Distance approx 7.86 km from Shepherdstown Show on Map

                                                                    6

                                                                    Light Horse Inn: Suite 3

                                                                    West Virginia / Harpers Ferry

                                                                    Harpers Ferry house

                                                                    1 2 min stay varies

                                                                    • 1 bedroom
                                                                    • sleeps 2
                                                                    • min stay varies
                                                                    • Ask about children
                                                                    • Air conditioning

                                                                    Price per night from

                                                                    $178

                                                                    Price per night from

                                                                    $178

                                                                    Distance approx 7.86 km from Shepherdstown Show on Map

                                                                      8

                                                                      Light Horse Inn: Suite 1

                                                                      West Virginia / Harpers Ferry

                                                                      Harpers Ferry house

                                                                      1 2 min stay varies

                                                                      • 1 bedroom
                                                                      • sleeps 2
                                                                      • min stay varies
                                                                      • Ask about children
                                                                      • Air conditioning

                                                                      Price per night from

                                                                      $195

                                                                      Price per night from

                                                                      $195

                                                                      Distance approx 7.86 km from Shepherdstown Show on Map

                                                                        11

                                                                        Vacation Rental: Riley House

                                                                        West Virginia / Harpers Ferry

                                                                        Harpers Ferry house

                                                                        4 8 min stay varies

                                                                        • 4 bedrooms
                                                                        • sleeps 8
                                                                        • min stay varies
                                                                        • Ask about children
                                                                        • Air conditioning
                                                                        • Pet Friendly

                                                                        Price per night from

                                                                        $281

                                                                        Price per night from

                                                                        $281

                                                                        Distance approx 7.83 km from Shepherdstown Show on Map

                                                                          9

                                                                          Vacation Rental: Canal House Cottage

                                                                          West Virginia / Harpers Ferry

                                                                          Harpers Ferry cottage

                                                                          1 3 min stay varies

                                                                          • 1 bedroom
                                                                          • sleeps 3
                                                                          • min stay varies
                                                                          • Ask about children
                                                                          • Air conditioning
                                                                          • Pet Friendly

                                                                          Price per night from

                                                                          $149

                                                                          Price per night from

                                                                          $149

                                                                          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