Winston goes far beyond Pi-Hole, even without the Winston browser extensions.

A Pi-Hole provides the ability for you to specify domains to block and ad-blocking. But for ad-blocking it provides just host blocking. 

Even without the Winston browser extensions, Winston provides this additional protection which Pi-Hole does not:

- Ad blocking based on request filtering, which is much more accurate than the host blocking which Pi-Hole provides

- DNS encryption, with protection against DNS rebinding attacks.

- A customizable, automatically updated blocklist of tracking and malware sites, to which you can add from well-known third-party blocklists and filters

- Distributed Privacy Mesh Network for IP scrambling

- A firewall

 In addition, Winston adds these with the Winston browser extension:

- Traffic analysis to analyze privacy risk and change security policies, modifying cookies intelligently and blocking risky connections

- Anti-fingerprinting

- On-the-fly whitelisting

Plus, with Winston, you're not managing a system of hardware and extensions on your own that may or may not work well together.