I grew up just outside Woking (Byfleet/West Byfleet) and attended Esher sixth form college (10 mins walk from Sandown Park) so that whole Weybridge/Walton etc area is well known to me, albeit I've only been back sporadically in recent decades. None of the places downwind of Esher are going to have anywhere near the vibrancy you'd get in Kingston etc.
Are you going midweek or at the weekend? This area mostly acts as dormitory towns and villages for commuters so will be fairly quiet in terms of busy pubs/restaurants etc midweek but a fair bit busier at weekends. I don't drive so my knowledge is largely restricted to the towns along the mainline train route.
Here's the first eight heading out beyond Esher, starting at the furthest away:
Guildford: Would be my first choice as someone who loves cobbled streets and quaint town pubs. It's has the only real postcard-style attractive areas on this list (albeit mixed in with modern stuff). There's a river, castle, (modern) cathedral and plenty of hotels being a minor 'tourist destination'. Is furthest from Sandown Park of these places though and possibly not the cheapest.
Worplesdon: Is literally just a train station in a field.
Woking: The biggest town in this list, circa 70k population in the town itself so similar to Wrexham (although Wrexham has more populous outlying towns and villages). Maybe similar in size to Kingston and equally mostly retail focused with a large shopping centre and newly built skyscrapers, but just a pissy canal rather than a river. Hosts a lot of obscure business conferences so plenty of hotel rooms and chain restaurants. A few pubs but almost all pretty generic towny chain places. Good place to chat non-league football with locals though. Woking FC came 2nd in the conference several times when I was a kid - back in the days when only one team got promoted, d'oh!
West Byfleet: A giant Waitrose, two pubs, 17 estate agents and not much else.
Byfleet & New Haw: Even less, and I say that as someone who part owns a restaurant in Byfleet!
Weybridge: One of the poshest places in the UK (the Beatles pretty much all lived in its St George's Hill area in their heyday). Has a couple of nice pubs and wine bars, some posh restaurants, might be worth considering to impress a lady but not much in the way of hotels I don't think. Brooklands racetrack (inc Mercedes museum) is a mile away if you haven't been and like motorsport.
Walton-on-Thames: Basically just Woking but a third of the size and with a river (and most of Thames Water's reservoirs) instead of a tiny canal.
Hersham: Punk band Sham 69's formation is more or less the only thing that has ever happened here.
Places not on the main trainline but spur lines (eg Addlestone, Chertsey, Cobham etc) are mostly much of a muchness, essentially middle class commuter villages with a 10-15k population and not a huge amount happening, especially midweek.
My blatherings above are probably not much help, but there you go.
