diff --git a/.changes/unreleased/ENHANCEMENTS-20230629-144119.yaml b/.changes/unreleased/ENHANCEMENTS-20230629-144119.yaml
new file mode 100644
index 00000000..16982145
--- /dev/null
+++ b/.changes/unreleased/ENHANCEMENTS-20230629-144119.yaml
@@ -0,0 +1,6 @@
+kind: ENHANCEMENTS
+body: 'generate: Prevent files and subdirectories in the rendered website directory
+  that are not directly managed by `tfplugindocs` from being deleted during generation'
+time: 2023-06-29T14:41:19.134991-04:00
+custom:
+  Issue: "267"
diff --git a/.changes/unreleased/ENHANCEMENTS-20230706-111427.yaml b/.changes/unreleased/ENHANCEMENTS-20230706-111427.yaml
new file mode 100644
index 00000000..2f5c35d6
--- /dev/null
+++ b/.changes/unreleased/ENHANCEMENTS-20230706-111427.yaml
@@ -0,0 +1,5 @@
+kind: ENHANCEMENTS
+body: 'validate: Add `cdktf` to list of allowed rendered website subdirectories'
+time: 2023-07-06T11:14:27.351158-04:00
+custom:
+  Issue: "267"
diff --git a/go.mod b/go.mod
index d1bf9e04..448b2577 100644
--- a/go.mod
+++ b/go.mod
@@ -12,6 +12,7 @@ require (
 	github.com/mitchellh/cli v1.1.5
 	github.com/russross/blackfriday v1.6.0
 	github.com/zclconf/go-cty v1.13.2
+	golang.org/x/exp v0.0.0-20230626212559-97b1e661b5df
 	golang.org/x/text v0.11.0
 )
 
@@ -40,6 +41,6 @@ require (
 	github.com/shopspring/decimal v1.3.1 // indirect
 	github.com/spf13/cast v1.5.0 // indirect
 	golang.org/x/crypto v0.8.0 // indirect
-	golang.org/x/mod v0.10.0 // indirect
+	golang.org/x/mod v0.11.0 // indirect
 	golang.org/x/sys v0.7.0 // indirect
 )
diff --git a/go.sum b/go.sum
index f0b0234e..5ce176d4 100644
--- a/go.sum
+++ b/go.sum
@@ -118,8 +118,10 @@ golang.org/x/crypto v0.0.0-20200820211705-5c72a883971a/go.mod h1:LzIPMQfyMNhhGPh
 golang.org/x/crypto v0.0.0-20210921155107-089bfa567519/go.mod h1:GvvjBRRGRdwPK5ydBHafDWAxML/pGHZbMvKqRZ5+Abc=
 golang.org/x/crypto v0.8.0 h1:pd9TJtTueMTVQXzk8E2XESSMQDj/U7OUu0PqJqPXQjQ=
 golang.org/x/crypto v0.8.0/go.mod h1:mRqEX+O9/h5TFCrQhkgjo2yKi0yYA+9ecGkdQoHrywE=
-golang.org/x/mod v0.10.0 h1:lFO9qtOdlre5W1jxS3r/4szv2/6iXxScdzjoBMXNhYk=
-golang.org/x/mod v0.10.0/go.mod h1:iBbtSCu2XBx23ZKBPSOrRkjjQPZFPuis4dIYUhu/chs=
+golang.org/x/exp v0.0.0-20230626212559-97b1e661b5df h1:UA2aFVmmsIlefxMk29Dp2juaUSth8Pyn3Tq5Y5mJGME=
+golang.org/x/exp v0.0.0-20230626212559-97b1e661b5df/go.mod h1:FXUEEKJgO7OQYeo8N01OfiKP8RXMtf6e8aTskBGqWdc=
+golang.org/x/mod v0.11.0 h1:bUO06HqtnRcc/7l71XBe4WcqTZ+3AH1J59zWDDwLKgU=
+golang.org/x/mod v0.11.0/go.mod h1:iBbtSCu2XBx23ZKBPSOrRkjjQPZFPuis4dIYUhu/chs=
 golang.org/x/net v0.0.0-20190404232315-eb5bcb51f2a3/go.mod h1:t9HGtf8HONx5eT2rtn7q6eTqICYqUVnKs3thJo3Qplg=
 golang.org/x/net v0.0.0-20210226172049-e18ecbb05110/go.mod h1:m0MpNAwzfU5UDzcl9v0D8zg8gWTRqZa9RBIspLL5mdg=
 golang.org/x/net v0.9.0 h1:aWJ/m6xSmxWBx+V0XRHTlrYrPG56jKsLdTFmsSsCzOM=
diff --git a/internal/provider/generate.go b/internal/provider/generate.go
index 71fd1f8a..b4c3293f 100644
--- a/internal/provider/generate.go
+++ b/internal/provider/generate.go
@@ -8,6 +8,7 @@ import (
 	"fmt"
 	"os"
 	"os/exec"
+	"path"
 	"path/filepath"
 	"runtime"
 	"strings"
@@ -22,6 +23,7 @@ import (
 	"github.com/hashicorp/terraform-exec/tfexec"
 	tfjson "github.com/hashicorp/terraform-json"
 	"github.com/mitchellh/cli"
+	"golang.org/x/exp/slices"
 )
 
 var (
@@ -63,6 +65,16 @@ var (
 		providerFileTemplate("index.html.markdown"),
 		providerFileTemplate("index.html.md"),
 	}
+
+	managedWebsiteSubDirectories = []string{
+		"data-sources",
+		"guides",
+		"resources",
+	}
+
+	managedWebsiteFiles = []string{
+		"index.md",
+	}
 )
 
 type generator struct {
@@ -416,11 +428,34 @@ func (g *generator) renderMissingDocs(providerName string, providerSchema *tfjso
 
 func (g *generator) renderStaticWebsite(providerName string, providerSchema *tfjson.ProviderSchema) error {
 	g.infof("cleaning rendered website dir")
-	err := os.RemoveAll(g.ProviderDocsDir())
+	dirEntry, err := os.ReadDir(g.ProviderDocsDir())
 	if err != nil {
 		return err
 	}
 
+	for _, file := range dirEntry {
+
+		// Remove subdirectories managed by tfplugindocs
+		if file.IsDir() && slices.Contains(managedWebsiteSubDirectories, file.Name()) {
+			g.infof("removing directory: %q", file.Name())
+			err = os.RemoveAll(path.Join(g.ProviderDocsDir(), file.Name()))
+			if err != nil {
+				return err
+			}
+			continue
+		}
+
+		// Remove files managed by tfplugindocs
+		if !file.IsDir() && slices.Contains(managedWebsiteFiles, file.Name()) {
+			g.infof("removing file: %q", file.Name())
+			err = os.RemoveAll(path.Join(g.ProviderDocsDir(), file.Name()))
+			if err != nil {
+				return err
+			}
+			continue
+		}
+	}
+
 	shortName := providerShortName(providerName)
 
 	g.infof("rendering templated website to static markdown")
diff --git a/internal/provider/validate.go b/internal/provider/validate.go
index c2748e80..329e05d1 100644
--- a/internal/provider/validate.go
+++ b/internal/provider/validate.go
@@ -98,6 +98,7 @@ func validateStaticDocs(ui cli.Ui, dir string) error {
 			"data-sources",
 			"guides",
 			"resources",
+			"cdktf",
 		),
 		checkBlockedExtensions(
 			".html.md.tmpl",