Hello,
We're doing an 8 day trek along the Alentejo coastal region south of Lisbon, Portugal. After the trek we'd like to stay an extra 2-3 days to relax within a 30 min train ride to Lisbon for our return flight home. We like quiet, charming towns with decent restaurants, maybe get a massage, take a yoga class, do a little shopping, meander the charming streets, etc. Can you recommend such a town? Can you also recommend a quiet, charming bed&breakfast or Inn that's reasonably priced? Thanks! Charlie

Hi Charlie,
See Obidos as a nice and charming villa inside a castle and look for West Holidays Portugal as the place to stay! You'll be amazed by the Silvercoast warm people.
Kind regards,
Ricardo
I recommend Almada, just across the 25th April Bridge. A nice little town on the beach, some superb fish restaurants and Parque de Paz is a very pleasant stroll round too.
It's just south across the bridge and once crossed, you're there.

Well,
i'm the last person in the world to say that you shouldn't go to Óbidos (i love it lol) but i should notice that Óbidos is by no means located in the Lisbon's suburban area served by train, so you'll need to take or the direct regional train, the Western Line (trip last about 2 hours) or the suburban train until Mira Sintra-Meleças and then take the regional line until Óbidos (this one will take 2 hours to 20 minutes or 30 minutes).
I can also recommend Sintra, of course.
I stayed out in Cascais, which is really just a suburb of Lisbon, but not really an independent town anymore.
Sintra has more of a town feel

Where on Earth did you get that info from?
I'm sorry, but Cascais has nothing to do with Lisbon whatsoever.
Cascais is a Vila (which in English translates as a Town), seat of one parish and the seat of the Municipality of the same name.
In Portugal, each elected Mayor runs one Municipality. So there's one Mayor of Cascais, running the entire territory of their corresponding Municipality. There are more than 200 thousand people living there, according to the latest census.
The Mayor of Lisbon runs only the territory of the Municipality of Lisbon, corresponding to the entire city of Lisbon. He doesn't have any power within Cascais.
Now if you wanna call Cascais a geographically suburb of Lisbon, it's fine, for better understanding, though i don't considered it since it's a little too far away (real suburbs are almost glued to the city, not 30 km away; for instance, Amadora also belongs to a different Municipality than Lisbon but is a real suburb of Lisbon, just a couple of km's away and it's served by one metro station and in future there will be at least another one there).
From an official statistical point of view, both Municipalities of Cascais and Lisbon belongs to the area known as Greater Lisbon.
Sorry for the off-topic, just a little bit of extra info.