diff --git a/builtin/myplugin/command/info.go b/builtin/myplugin/command/info.go
index 0199f4705..93b2ad244 100644
--- a/builtin/myplugin/command/info.go
+++ b/builtin/myplugin/command/info.go
@@ -79,12 +79,12 @@ func (c *Info) Execute(trm terminal.UI, p plugincore.Project) int32 {
 	defaultPrivateKeyPath, _ := p.DefaultPrivateKey()
 
 	trm.Output("\nEnvironment information")
-	trm.Output("Working directory: " + cwd)
+	trm.Output("Working directory: " + cwd.String())
 	trm.Output("Data directory: " + datadir.DataDir().String())
 	trm.Output("Vagrantfile name: " + vagrantfileName)
-	trm.Output("Home directory: " + home)
-	trm.Output("Local data directory: " + localDataPath)
-	trm.Output("Default private key path: " + defaultPrivateKeyPath)
+	trm.Output("Home directory: " + home.String())
+	trm.Output("Local data directory: " + localDataPath.String())
+	trm.Output("Default private key path: " + defaultPrivateKeyPath.String())
 
 	return 0
 }
diff --git a/builtin/otherplugin/command.go b/builtin/otherplugin/command.go
index 9061769e2..d8e95cb28 100644
--- a/builtin/otherplugin/command.go
+++ b/builtin/otherplugin/command.go
@@ -116,14 +116,14 @@ func (c *Command) ExecuteInfo(trm terminal.UI, p plugincore.Project) int32 {
 	defaultPrivateKeyPath, _ := p.DefaultPrivateKey()
 
 	trm.Output("\nEnvironment information")
-	trm.Output("Working directory: " + cwd)
+	trm.Output("Working directory: " + cwd.String())
 	if datadir != nil && datadir.DataDir() != nil {
 		trm.Output("Data directory: " + datadir.DataDir().String())
 	}
 	trm.Output("Vagrantfile name: " + vagrantfileName)
-	trm.Output("Home directory: " + home)
-	trm.Output("Local data directory: " + localDataPath)
-	trm.Output("Default private key path: " + defaultPrivateKeyPath)
+	trm.Output("Home directory: " + home.String())
+	trm.Output("Local data directory: " + localDataPath.String())
+	trm.Output("Default private key path: " + defaultPrivateKeyPath.String())
 
 	ptrm, err := p.UI()
 	if err != nil {
diff --git a/internal/core/basis.go b/internal/core/basis.go
index 3923d7abc..75016f4b9 100644
--- a/internal/core/basis.go
+++ b/internal/core/basis.go
@@ -239,12 +239,8 @@ func (b *Basis) Config() *vagrant_plugin_sdk.Vagrantfile_Vagrantfile {
 	return b.basis.Configuration
 }
 
-func (p *Basis) CWD() (path string, err error) {
-	cwd, err := paths.VagrantCwd()
-	if err != nil {
-		return "", err
-	}
-	return cwd.String(), nil
+func (p *Basis) CWD() (path path.Path, err error) {
+	return paths.VagrantCwd()
 }
 
 // Basis UI is the "default" UI with no prefix modifications
@@ -258,9 +254,8 @@ func (b *Basis) DataDir() (*datadir.Basis, error) {
 }
 
 // DefaultPrivateKey implements core.Basis
-func (b *Basis) DefaultPrivateKey() (path string, err error) {
-	defaultPrivateKeyPath := b.dir.DataDir().Join("insecure_private_key")
-	return defaultPrivateKeyPath.String(), nil
+func (b *Basis) DefaultPrivateKey() (path path.Path, err error) {
+	return b.dir.DataDir().Join("insecure_private_key"), nil
 }
 
 // Implements core.Basis
diff --git a/internal/core/box.go b/internal/core/box.go
index 79b79f4f9..28c133ef8 100644
--- a/internal/core/box.go
+++ b/internal/core/box.go
@@ -17,6 +17,7 @@ import (
 	"github.com/hashicorp/go-multierror"
 	"github.com/hashicorp/go-version"
 	"github.com/hashicorp/vagrant-plugin-sdk/core"
+	"github.com/hashicorp/vagrant-plugin-sdk/helper/path"
 	"github.com/hashicorp/vagrant-plugin-sdk/proto/vagrant_plugin_sdk"
 	"github.com/hashicorp/vagrant/internal/server/proto/vagrant_server"
 	"github.com/mitchellh/mapstructure"
@@ -232,8 +233,8 @@ func (b *Box) Destroy() (err error) {
 	return
 }
 
-func (b *Box) Directory() (path string, err error) {
-	return b.box.Directory, nil
+func (b *Box) Directory() (path.Path, error) {
+	return path.NewPath(b.box.Directory), nil
 }
 
 // Checks if the box has an update and returns the metadata, version,
@@ -345,11 +346,11 @@ func (b *Box) Provider() (name string, err error) {
 }
 
 // This repackages this box and outputs it to the given path.
-func (b *Box) Repackage(outputPath string) (err error) {
+func (b *Box) Repackage(outputPath path.Path) (err error) {
 	b.logger.Trace("repackaging box", b.box.Name,
 		"to", outputPath)
 
-	tarFile, err := os.Create(outputPath)
+	tarFile, err := os.Create(outputPath.String())
 	if err != nil {
 		return err
 	}
diff --git a/internal/core/box_collection.go b/internal/core/box_collection.go
index 6a39f39ef..12cd62ce8 100644
--- a/internal/core/box_collection.go
+++ b/internal/core/box_collection.go
@@ -12,6 +12,7 @@ import (
 	"github.com/hashicorp/go-getter"
 	"github.com/hashicorp/go-hclog"
 	"github.com/hashicorp/vagrant-plugin-sdk/core"
+	"github.com/hashicorp/vagrant-plugin-sdk/helper/path"
 	"github.com/hashicorp/vagrant-plugin-sdk/proto/vagrant_plugin_sdk"
 	"github.com/hashicorp/vagrant/internal/server/proto/vagrant_server"
 	"google.golang.org/protobuf/types/known/emptypb"
@@ -45,9 +46,9 @@ func NewBoxCollection(basis *Basis, dir string, logger hclog.Logger) (bc *BoxCol
 // * BoxProviderDoesntMatch - If the given box provider doesn't match the
 // 	actual box provider in the untarred box.
 // * BoxUnpackageFailure - An invalid tar file.
-func (b *BoxCollection) Add(path, name, version, metadataURL string, force bool, providers ...string) (box core.Box, err error) {
-	if _, err := os.Stat(path); err != nil {
-		return nil, fmt.Errorf("Could not add box, unable to find path %s", path)
+func (b *BoxCollection) Add(p path.Path, name, version, metadataURL string, force bool, providers ...string) (box core.Box, err error) {
+	if _, err := os.Stat(p.String()); err != nil {
+		return nil, fmt.Errorf("Could not add box, unable to find path %s", p.String())
 	}
 	exists, err := b.Find(name, version, providers...)
 	if err != nil {
@@ -70,7 +71,7 @@ func (b *BoxCollection) Add(path, name, version, metadataURL string, force bool,
 	} // delete tempdir when finished
 	defer os.RemoveAll(tempDir)
 	b.logger.Debug("Unpacking box")
-	boxFile, err := os.Open(path)
+	boxFile, err := os.Open(p.String())
 	if err != nil {
 		return nil, err
 	}
@@ -86,7 +87,7 @@ func (b *BoxCollection) Add(path, name, version, metadataURL string, force bool,
 		ext = "tar.gz"
 	}
 	decompressor := getter.Decompressors[ext]
-	err = decompressor.Decompress(tempDir, path, true, os.ModeDir)
+	err = decompressor.Decompress(tempDir, p.String(), true, os.ModeDir)
 	if err != nil {
 		return nil, err
 	}
@@ -112,7 +113,7 @@ func (b *BoxCollection) Add(path, name, version, metadataURL string, force bool,
 			}
 		}
 		if !foundProvider {
-			return nil, fmt.Errorf("could not add box %s, provider '%s' does not match the expected providers %s", path, provider, providers)
+			return nil, fmt.Errorf("could not add box %s, provider '%s' does not match the expected providers %s", p.String(), provider, providers)
 		}
 	}
 
diff --git a/internal/core/project.go b/internal/core/project.go
index 81e009d56..e374cf61c 100644
--- a/internal/core/project.go
+++ b/internal/core/project.go
@@ -84,12 +84,8 @@ func (b *Project) Config() (*vagrant_plugin_sdk.Vagrantfile_Vagrantfile, error)
 }
 
 // CWD implements core.Project
-func (p *Project) CWD() (path string, err error) {
-	cwd, err := paths.VagrantCwd()
-	if err != nil {
-		return "", err
-	}
-	return cwd.String(), nil
+func (p *Project) CWD() (path path.Path, err error) {
+	return paths.VagrantCwd()
 }
 
 // DataDir implements core.Project
@@ -98,7 +94,7 @@ func (p *Project) DataDir() (*datadir.Project, error) {
 }
 
 // DefaultPrivateKey implements core.Project
-func (p *Project) DefaultPrivateKey() (path string, err error) {
+func (p *Project) DefaultPrivateKey() (path path.Path, err error) {
 	return p.basis.DefaultPrivateKey()
 }
 
@@ -109,8 +105,8 @@ func (p *Project) DefaultProvider() (name string, err error) {
 }
 
 // Home implements core.Project
-func (p *Project) Home() (path string, err error) {
-	return p.project.Path, nil
+func (p *Project) Home() (dir path.Path, err error) {
+	return path.NewPath(p.project.Path), nil
 }
 
 // Host implements core.Project
@@ -119,8 +115,8 @@ func (p *Project) Host() (host core.Host, err error) {
 }
 
 // LocalData implements core.Project
-func (p *Project) LocalData() (path string, err error) {
-	return p.dir.DataDir().String(), nil
+func (p *Project) LocalData() (d path.Path, err error) {
+	return p.dir.DataDir(), nil
 }
 
 // PrimaryTargetName implements core.Project
@@ -135,7 +131,7 @@ func (p *Project) ResourceId() (string, error) {
 }
 
 // RootPath implements core.Project
-func (p *Project) RootPath() (path string, err error) {
+func (p *Project) RootPath() (path path.Path, err error) {
 	// TODO: need vagrantfile loading to be completed in order to implement
 	return
 }
@@ -190,8 +186,8 @@ func (p *Project) TargetNames() ([]string, error) {
 }
 
 // Tmp implements core.Project
-func (p *Project) Tmp() (path string, err error) {
-	return p.dir.TempDir().String(), nil
+func (p *Project) Tmp() (path path.Path, err error) {
+	return p.dir.TempDir(), nil
 }
 
 // UI implements core.Project