Lisbon
Hotel das Amoreiras
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I think this is the best hotel in the city, hands down. A small boutique launched and operated by a Portuguese couple who worked in Swiss finance and wanted to bring something charming and tasteful to the city. Hidden adjacent to a park that runs underneath an aquaduct. Phenomenal breakfast and a really solid bar. Most “hidden gems” are exagerrated; this is not.
Hotel Memmo
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The best views of any hotel in the city and located about one hill away from the crowded, touristy areas where other hotels sit. Close enough to stroll down to whatever you want to see but away from the crowds and secluded.
Sintra
I generally recommend Sintra being a day trip for most folks. The actual town is closer than you think (30-35 minutes by car).