diff --git a/CHANGELOG.md b/CHANGELOG.md
index 683c073be..22db22da6 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -1,5 +1,10 @@
 # Unreleased
 
+### Features
+
+-   Improved support for `--entryPointStrategy Packages`. TypeDoc will now load package-specific configurations from `package.json` `typedoc` field. This configuration allows configuring a custom display name (`typedoc.displayName`) field, entry point (`typedoc.entryPoint` - this is equivalent and will override `typedocMain`), and path to a readme file to be rendered at the top of the package page (`typedoc.readmeFile`), #1658.
+-   The `--includeVersion` option will now be respected by `--entryPointStrategy Packages`. Also, for this combination, missing `version` field in the root `package.json` will not issue a warning.
+
 ## v0.23.5 (2022-07-02)
 
 ### Features
diff --git a/src/lib/converter/converter.ts b/src/lib/converter/converter.ts
index 132134ba4..f94444d18 100644
--- a/src/lib/converter/converter.ts
+++ b/src/lib/converter/converter.ts
@@ -5,7 +5,7 @@ import { ProjectReflection, ReflectionKind, SomeType } from "../models/index";
 import { Context } from "./context";
 import { ConverterComponent } from "./components";
 import { Component, ChildableComponent } from "../utils/component";
-import { BindOption } from "../utils";
+import { BindOption, MinimalSourceFile, readFile } from "../utils";
 import { convertType } from "./types";
 import { ConverterEvents } from "./converter-events";
 import { convertSymbol } from "./symbols";
@@ -15,6 +15,8 @@ import { hasAllFlags, hasAnyFlag } from "../utils/enum";
 import type { DocumentationEntryPoint } from "../utils/entry-point";
 import { CommentParserConfig, getComment } from "./comments";
 import type { CommentStyle } from "../utils/options/declaration";
+import { parseComment } from "./comments/parser";
+import { lexCommentString } from "./comments/rawLexer";
 
 /**
  * Compiles source files using TypeScript and converts compiler symbols to reflections.
@@ -201,9 +203,8 @@ export class Converter extends ChildableComponent<
             context.setActiveProgram(e.entryPoint.program);
             e.context = this.convertExports(
                 context,
-                e.entryPoint.sourceFile,
-                entries.length === 1,
-                e.entryPoint.displayName
+                e.entryPoint,
+                entries.length === 1
             );
         });
         for (const { entryPoint, context } of entries) {
@@ -218,10 +219,11 @@ export class Converter extends ChildableComponent<
 
     private convertExports(
         context: Context,
-        node: ts.SourceFile,
-        singleEntryPoint: boolean,
-        entryName: string
+        entryPoint: DocumentationEntryPoint,
+        singleEntryPoint: boolean
     ) {
+        const node = entryPoint.sourceFile;
+        const entryName = entryPoint.displayName;
         const symbol = getSymbolForModuleLike(context, node);
         let moduleContext: Context;
 
@@ -259,6 +261,33 @@ export class Converter extends ChildableComponent<
                 void 0,
                 entryName
             );
+
+            if (entryPoint.readmeFile) {
+                const readme = readFile(entryPoint.readmeFile);
+                const comment = parseComment(
+                    lexCommentString(readme),
+                    context.converter.config,
+                    new MinimalSourceFile(readme, entryPoint.readmeFile),
+                    context.logger
+                );
+
+                if (comment.blockTags.length || comment.modifierTags.size) {
+                    const ignored = [
+                        ...comment.blockTags.map((tag) => tag.tag),
+                        ...comment.modifierTags,
+                    ];
+                    context.logger.warn(
+                        `Block and modifier tags will be ignored within the readme:\n\t${ignored.join(
+                            "\n\t"
+                        )}`
+                    );
+                }
+
+                reflection.readme = comment.summary;
+            }
+
+            reflection.version = entryPoint.version;
+
             context.finalizeDeclarationReflection(reflection);
             moduleContext = context.withScope(reflection);
         }
diff --git a/src/lib/converter/plugins/LinkResolverPlugin.ts b/src/lib/converter/plugins/LinkResolverPlugin.ts
index 78be33191..714f2f1f3 100644
--- a/src/lib/converter/plugins/LinkResolverPlugin.ts
+++ b/src/lib/converter/plugins/LinkResolverPlugin.ts
@@ -10,6 +10,7 @@ import type {
     CommentDisplayPart,
     InlineTagDisplayPart,
 } from "../../models/comments";
+import { DeclarationReflection } from "../../models";
 
 const urlPrefix = /^(http|ftp)s?:\/\//;
 const brackets = /\[\[([^\]]+)\]\]/g;
@@ -136,6 +137,14 @@ export class LinkResolverPlugin extends ConverterComponent {
         for (const tag of comment.blockTags) {
             tag.content = this.processParts(reflection, tag.content, warn);
         }
+
+        if (reflection instanceof DeclarationReflection && reflection.readme) {
+            reflection.readme = this.processParts(
+                reflection,
+                reflection.readme,
+                warn
+            );
+        }
     }
 
     private processParts(
diff --git a/src/lib/converter/plugins/PackagePlugin.ts b/src/lib/converter/plugins/PackagePlugin.ts
index 29309d95d..f48b43a87 100644
--- a/src/lib/converter/plugins/PackagePlugin.ts
+++ b/src/lib/converter/plugins/PackagePlugin.ts
@@ -4,7 +4,7 @@ import * as FS from "fs";
 import { Component, ConverterComponent } from "../components";
 import { Converter } from "../converter";
 import type { Context } from "../context";
-import { BindOption, readFile } from "../../utils";
+import { BindOption, EntryPointStrategy, readFile } from "../../utils";
 import { getCommonDirectory } from "../../utils/fs";
 import { nicePath } from "../../utils/paths";
 import { lexCommentString } from "../comments/rawLexer";
@@ -23,6 +23,9 @@ export class PackagePlugin extends ConverterComponent {
     @BindOption("includeVersion")
     includeVersion!: boolean;
 
+    @BindOption("entryPointStrategy")
+    entryPointStrategy!: EntryPointStrategy;
+
     /**
      * The file name of the found readme.md file.
      */
@@ -140,9 +143,15 @@ export class PackagePlugin extends ConverterComponent {
                 if (packageInfo.version) {
                     project.name = `${project.name} - v${packageInfo.version}`;
                 } else {
-                    context.logger.warn(
-                        "--includeVersion was specified, but package.json does not specify a version."
-                    );
+                    // since not all monorepo specifies a meaningful version to the main package.json
+                    // this warning should be optional
+                    if (
+                        this.entryPointStrategy !== EntryPointStrategy.Packages
+                    ) {
+                        context.logger.warn(
+                            "--includeVersion was specified, but package.json does not specify a version."
+                        );
+                    }
                 }
             }
         } else {
@@ -153,9 +162,13 @@ export class PackagePlugin extends ConverterComponent {
                 project.name = "Documentation";
             }
             if (this.includeVersion) {
-                context.logger.warn(
-                    "--includeVersion was specified, but no package.json was found. Not adding package version to the documentation."
-                );
+                // since not all monorepo specifies a meaningful version to the main package.json
+                // this warning should be optional
+                if (this.entryPointStrategy !== EntryPointStrategy.Packages) {
+                    context.logger.warn(
+                        "--includeVersion was specified, but no package.json was found. Not adding package version to the documentation."
+                    );
+                }
             }
         }
     }
diff --git a/src/lib/models/reflections/declaration.ts b/src/lib/models/reflections/declaration.ts
index 540918a5b..9c0db2b0f 100644
--- a/src/lib/models/reflections/declaration.ts
+++ b/src/lib/models/reflections/declaration.ts
@@ -5,6 +5,7 @@ import { ContainerReflection } from "./container";
 import type { SignatureReflection } from "./signature";
 import type { TypeParameterReflection } from "./type-parameter";
 import type { Serializer, JSONOutput } from "../../serialization";
+import type { CommentDisplayPart } from "../comments";
 
 /**
  * Stores hierarchical type data.
@@ -129,6 +130,16 @@ export class DeclarationReflection extends ContainerReflection {
      */
     typeHierarchy?: DeclarationHierarchy;
 
+    /**
+     * The contents of the readme file of the module when found.
+     */
+    readme?: CommentDisplayPart[];
+
+    /**
+     * The version of the module when found.
+     */
+    version?: string;
+
     override hasGetterOrSetter(): boolean {
         return !!this.getSignature || !!this.setSignature;
     }
diff --git a/src/lib/output/themes/default/partials/header.tsx b/src/lib/output/themes/default/partials/header.tsx
index 29e9d13f9..d8d4e5a3e 100644
--- a/src/lib/output/themes/default/partials/header.tsx
+++ b/src/lib/output/themes/default/partials/header.tsx
@@ -2,7 +2,7 @@ import { hasTypeParameters, join, renderFlags } from "../../lib";
 import { JSX } from "../../../../utils";
 import type { DefaultThemeRenderContext } from "../DefaultThemeRenderContext";
 import type { PageEvent } from "../../../events";
-import type { Reflection } from "../../../../models";
+import { DeclarationReflection, Reflection } from "../../../../models";
 
 export const header = (context: DefaultThemeRenderContext, props: PageEvent<Reflection>) => {
     const HeadingLevel = props.model.isProject() ? "h2" : "h1";
@@ -12,6 +12,9 @@ export const header = (context: DefaultThemeRenderContext, props: PageEvent<Refl
             <HeadingLevel>
                 {props.model.kindString !== "Project" && `${props.model.kindString ?? ""} `}
                 {props.model.name}
+                {props.model instanceof DeclarationReflection &&
+                    props.model.version !== undefined &&
+                    ` - v${props.model.version}`}
                 {hasTypeParameters(props.model) && (
                     <>
                         {"<"}
diff --git a/src/lib/output/themes/default/partials/index.tsx b/src/lib/output/themes/default/partials/index.tsx
index b0e895c99..ff0e46945 100644
--- a/src/lib/output/themes/default/partials/index.tsx
+++ b/src/lib/output/themes/default/partials/index.tsx
@@ -1,7 +1,7 @@
-import { classNames, wbr } from "../../lib";
+import { classNames, displayPartsToMarkdown, wbr } from "../../lib";
 import type { DefaultThemeRenderContext } from "../DefaultThemeRenderContext";
-import { JSX } from "../../../../utils";
-import type { ContainerReflection, ReflectionCategory } from "../../../../models";
+import { JSX, Raw } from "../../../../utils";
+import { ContainerReflection, DeclarationReflection, ReflectionCategory, ReflectionKind } from "../../../../models";
 
 function renderCategory({ urlTo, icons }: DefaultThemeRenderContext, item: ReflectionCategory, prependName = "") {
     return (
@@ -67,8 +67,19 @@ export function index(context: DefaultThemeRenderContext, props: ContainerReflec
     }
 
     return (
-        <section class="tsd-panel-group tsd-index-group">
-            <section class="tsd-panel tsd-index-panel">{content}</section>
-        </section>
+        <>
+            {props instanceof DeclarationReflection &&
+                props.kind === ReflectionKind.Module &&
+                props.readme?.length !== 0 && (
+                    <section class="tsd-panel-group">
+                        <section class="tsd-panel tsd-typography">
+                            <Raw html={context.markdown(displayPartsToMarkdown(props.readme || [], context.urlTo))} />
+                        </section>
+                    </section>
+                )}
+            <section class="tsd-panel-group tsd-index-group">
+                <section class="tsd-panel tsd-index-panel">{content}</section>
+            </section>
+        </>
     );
 }
diff --git a/src/lib/output/themes/default/partials/navigation.tsx b/src/lib/output/themes/default/partials/navigation.tsx
index 7e7dcd477..bdf216b40 100644
--- a/src/lib/output/themes/default/partials/navigation.tsx
+++ b/src/lib/output/themes/default/partials/navigation.tsx
@@ -121,7 +121,9 @@ function primaryNavigation(context: DefaultThemeRenderContext, props: PageEvent<
 
         return (
             <li class={classNames({ current, selected, deprecated: mod.isDeprecated() }, mod.cssClasses)}>
-                <a href={context.urlTo(mod)}>{wbr(mod.name)}</a>
+                <a href={context.urlTo(mod)}>
+                    {wbr(`${mod.name}${mod.version !== undefined ? ` - v${mod.version}` : ""}`)}
+                </a>
                 {childNav}
             </li>
         );
diff --git a/src/lib/utils/entry-point.ts b/src/lib/utils/entry-point.ts
index b5b9e977a..3df6c28a2 100644
--- a/src/lib/utils/entry-point.ts
+++ b/src/lib/utils/entry-point.ts
@@ -1,13 +1,15 @@
 import { join, relative, resolve } from "path";
 import * as ts from "typescript";
 import * as FS from "fs";
+import * as Path from "path";
 import {
     expandPackages,
+    extractTypedocConfigFromPackageManifest,
     getTsEntryPointForPackage,
     ignorePackage,
     loadPackageManifest,
 } from "./package-manifest";
-import { createMinimatch, matchesAny } from "./paths";
+import { createMinimatch, matchesAny, nicePath } from "./paths";
 import type { Logger } from "./loggers";
 import type { Options } from "./options";
 import { getCommonDirectory, glob, normalizePath } from "./fs";
@@ -39,8 +41,10 @@ export type EntryPointStrategy =
 
 export interface DocumentationEntryPoint {
     displayName: string;
+    readmeFile?: string;
     program: ts.Program;
     sourceFile: ts.SourceFile;
+    version?: string;
 }
 
 export function getEntryPoints(
@@ -321,6 +325,10 @@ function getEntryPointsForPackages(
     for (const packagePath of expandedPackages) {
         const packageJsonPath = resolve(packagePath, "package.json");
         const packageJson = loadPackageManifest(logger, packageJsonPath);
+        const includeVersion = options.getValue("includeVersion");
+        const typedocPackageConfig = packageJson
+            ? extractTypedocConfigFromPackageManifest(logger, packageJsonPath)
+            : undefined;
         if (packageJson === undefined) {
             logger.error(`Could not load package manifest ${packageJsonPath}`);
             return;
@@ -383,8 +391,32 @@ function getEntryPointsForPackages(
             return;
         }
 
+        if (
+            includeVersion &&
+            (!packageJson["version"] ||
+                typeof packageJson["version"] !== "string")
+        ) {
+            logger.warn(
+                `--includeVersion was specified, but "${nicePath(
+                    packageJsonPath
+                )}" does not properly specify a version.`
+            );
+        }
+
         results.push({
-            displayName: packageJson["name"] as string,
+            displayName:
+                typedocPackageConfig?.displayName ??
+                (packageJson["name"] as string),
+            version: packageJson["version"] as string | undefined,
+            readmeFile: typedocPackageConfig?.readmeFile
+                ? Path.resolve(
+                      Path.join(
+                          packageJsonPath,
+                          "..",
+                          typedocPackageConfig?.readmeFile
+                      )
+                  )
+                : undefined,
             program,
             sourceFile,
         });
diff --git a/src/lib/utils/package-manifest.ts b/src/lib/utils/package-manifest.ts
index 753ad9c38..56fc65a88 100644
--- a/src/lib/utils/package-manifest.ts
+++ b/src/lib/utils/package-manifest.ts
@@ -6,7 +6,8 @@ import { existsSync } from "fs";
 import { readFile, glob } from "./fs";
 import type { Logger } from "./loggers";
 import type { IMinimatch } from "minimatch";
-import { matchesAny } from "./paths";
+import { matchesAny, nicePath } from "./paths";
+import { additionalProperties, Infer, optional, validate } from "./validation";
 
 /**
  * Helper for the TS type system to understand hasOwnProperty
@@ -36,6 +37,47 @@ export function loadPackageManifest(
     return packageJson as Record<string, unknown>;
 }
 
+const typedocPackageManifestConfigSchema = {
+    displayName: optional(String),
+    entryPoint: optional(String),
+    readmeFile: optional(String),
+
+    [additionalProperties]: false,
+};
+
+export type TypedocPackageManifestConfig = Infer<
+    typeof typedocPackageManifestConfigSchema
+>;
+
+/**
+ * Extracts typedoc specific config from a specified package manifest
+ */
+export function extractTypedocConfigFromPackageManifest(
+    logger: Logger,
+    packageJsonPath: string
+): TypedocPackageManifestConfig | undefined {
+    const packageJson = loadPackageManifest(logger, packageJsonPath);
+    if (!packageJson) {
+        return undefined;
+    }
+    if (
+        hasOwnProperty(packageJson, "typedoc") &&
+        typeof packageJson.typedoc == "object" &&
+        packageJson.typedoc
+    ) {
+        if (
+            !validate(typedocPackageManifestConfigSchema, packageJson.typedoc)
+        ) {
+            logger.error(
+                `Typedoc config extracted from package manifest file ${packageJsonPath} is not valid`
+            );
+            return undefined;
+        }
+        return packageJson.typedoc;
+    }
+    return undefined;
+}
+
 /**
  * Load the paths to packages specified in a Yarn workspace package JSON
  * Returns undefined if packageJSON does not define a Yarn workspace
@@ -205,10 +247,21 @@ export function getTsEntryPointForPackage(
 ): string | undefined | typeof ignorePackage {
     let packageMain = "index.js"; // The default, per the npm docs.
     let packageTypes = null;
-    if (
+    const typedocPackageConfig = extractTypedocConfigFromPackageManifest(
+        logger,
+        packageJsonPath
+    );
+    if (typedocPackageConfig?.entryPoint) {
+        packageMain = typedocPackageConfig.entryPoint;
+    } else if (
         hasOwnProperty(packageJson, "typedocMain") &&
         typeof packageJson.typedocMain == "string"
     ) {
+        logger.warn(
+            `Legacy typedoc entry point config (using "typedocMain" field) found for "${nicePath(
+                packageJsonPath
+            )}". Please update to use "typedoc": { "entryPoint": "..." } instead. In future upgrade, "typedocMain" field will be ignored.`
+        );
         packageMain = packageJson.typedocMain;
     } else if (
         hasOwnProperty(packageJson, "main") &&
diff --git a/src/test/packages.test.ts b/src/test/packages.test.ts
index 872d030a4..6ec429bc4 100644
--- a/src/test/packages.test.ts
+++ b/src/test/packages.test.ts
@@ -9,7 +9,7 @@ import {
 
 import { tempdirProject } from "@typestrong/fs-fixture-builder";
 import { TestLogger } from "./TestLogger";
-import { createMinimatch } from "../lib/utils/paths";
+import { createMinimatch, nicePath } from "../lib/utils/paths";
 
 describe("Packages support", () => {
     let project: ReturnType<typeof tempdirProject>;
@@ -63,16 +63,18 @@ describe("Packages support", () => {
         });
         project.addJsonFile("packages/baz/tsconfig.json", childTsconfig);
 
-        // Foo, entry point with "typedocMain"
-        project.addFile("packages/foo/dist/index.js", "module.exports = 123");
-        project.addFile("packages/foo/index.ts", "export function foo() {}");
-        project.addJsonFile("packages/foo/package.json", {
-            name: "typedoc-multi-package-foo",
+        // Bay, entry point with "typedoc.entryPoint"
+        project.addFile("packages/bay/dist/index.js", "module.exports = 123");
+        project.addFile("packages/bay/index.ts", "export function foo() {}");
+        project.addJsonFile("packages/bay/package.json", {
+            name: "typedoc-multi-package-bay",
             version: "1.0.0",
             main: "dist/index",
-            typedocMain: "index.ts",
+            typedoc: {
+                entryPoint: "index.ts",
+            },
         });
-        project.addJsonFile("packages/foo/tsconfig.json", childTsconfig);
+        project.addJsonFile("packages/bay/tsconfig.json", childTsconfig);
 
         // Ign, ignored package
         project.addFile("packages/ign/dist/index.js", "module.exports = 123");
@@ -81,7 +83,6 @@ describe("Packages support", () => {
             name: "typedoc-multi-package-ign",
             version: "1.0.0",
             main: "dist/index",
-            typedocMain: "index.ts",
         });
         project.addJsonFile("packages/ign/tsconfig.json", childTsconfig);
 
@@ -98,8 +99,8 @@ describe("Packages support", () => {
             packages,
             [
                 join(project.cwd, "packages/bar"),
+                join(project.cwd, "packages/bay"),
                 join(project.cwd, "packages/baz"),
-                join(project.cwd, "packages/foo"),
             ].map(normalizePath)
         );
 
@@ -114,14 +115,75 @@ describe("Packages support", () => {
 
         equal(entries, [
             join(project.cwd, "packages/bar/index.d.ts"),
+            join(project.cwd, "packages/bay/index.ts"),
             join(project.cwd, "packages/baz/index.ts"),
-            join(project.cwd, "packages/foo/index.ts"),
         ]);
 
         logger.discardDebugMessages();
         logger.expectNoOtherMessages();
     });
 
+    it("handles monorepos with legacy configuration", () => {
+        project.addJsonFile("tsconfig.json", {
+            compilerOptions: {
+                strict: true,
+                sourceMap: true,
+            },
+            exclude: ["node_modules", "dist"],
+        });
+        const childTsconfig = {
+            extends: "../../tsconfig.json",
+            compilerOptions: {
+                outDir: "dist",
+            },
+        };
+        project.addJsonFile("package.json", {
+            name: "typedoc-multi-package-example",
+            main: "dist/index.js",
+            workspaces: ["packages/*"],
+        });
+
+        // Foo, entry point with "typedocMain"
+        project.addFile("packages/foo/dist/index.js", "module.exports = 123");
+        project.addFile("packages/foo/index.ts", "export function foo() {}");
+        project.addJsonFile("packages/foo/package.json", {
+            name: "typedoc-multi-package-foo",
+            version: "1.0.0",
+            main: "dist/index",
+            typedocMain: "index.ts",
+        });
+        project.addJsonFile("packages/foo/tsconfig.json", childTsconfig);
+
+        project.write();
+        const logger = new TestLogger();
+        const packages = expandPackages(
+            logger,
+            project.cwd,
+            [project.cwd],
+            createMinimatch(["**/ign"])
+        );
+
+        equal(packages, [join(project.cwd, "packages/foo")].map(normalizePath));
+
+        const entries = packages.map((p) => {
+            const packageJson = join(p, "package.json");
+            return getTsEntryPointForPackage(
+                logger,
+                packageJson,
+                JSON.parse(readFileSync(packageJson, "utf-8"))
+            );
+        });
+
+        equal(entries, [join(project.cwd, "packages/foo/index.ts")]);
+
+        logger.discardDebugMessages();
+        logger.expectMessage(
+            `warn: Legacy typedoc entry point config (using "typedocMain" field) found for "${nicePath(
+                join(project.cwd, "/packages/foo/package.json")
+            )}". Please update to use "typedoc": { "entryPoint": "..." } instead. In future upgrade, "typedocMain" field will be ignored.`
+        );
+    });
+
     it("handles single packages", () => {
         project.addJsonFile("tsconfig.json", {
             compilerOptions: {