Negotiability of Hotel Prices

Short answer is no.

Portugal has high hotel occupancy and very occupancy in the areas sought-after by tourists in the season.

Some hotel chains offer member discounts, using aggregator sites ( ie: booking.com) helps to find nearby hotels at lower prices.

Lisbon has a good Metro system, you can book a cheaper hotel at a different location and use the Metro to get around.

Caveat: Lisbon is very hilly in some locations, something you should consider when choosing a location.

What I thought. Thank you.

You have to look at the $$$$ system as a tool to compare hotels relative to each other. That is, a $$$ hotel is more expensive than a $$ hotel. It's also relative to whichever city or country you are in - a $ hotel in Switzerland might be more expensive than a $$$ hotel in Greece. However, none of that estimation can keep up with the current market prices in any given location in any given season, especially when the underlying data is already 1+ years old when the book is published.

I too was a bit surprised at the hotel rates (and airbnb) in Lisbon over the last three weeks of May. Originally I had planned to spend our last three nights in Lisbon before our flight home on May 25....then I found out that Taylor Swift is performing in Lisbon two of the nights so no wonder the rates are high! I've read that many fans unable to afford or obtain concert tickets in the US purchased tickets to her Lisbon shows. I adjusted our itinerary and now we're exploring Lisbon about half way through our trip. Hotels rates were dramatically less.

Relatively speaking, the same $$ hotel in low season is still considered a $$ hotel during high season even though it may cost more than two to three times as much. The $ symbols just allow you to compare other hotels in the same area at the same time.

It has been decades since I backpacked and booked hotels on the fly. Nowadays, I reserve hotels months in advance. It might still be possible to walk into a small one or two star hotel in low season and negotiate a price with the proprietor. It couldn't hurt to try. However, even small crappy hotels are using the internet to book rooms in advance. And once you hit busy May-August, there really is little incentive to cut prices.

@cjohnson - what OH NO!!!!!! No wonder. That means there will be an additional 65K people that I don't want to be around in the city 2 of the 3 days I'm there! Dammit...I wish I had known that in advance, I would have stated in Lisbon instead of finishing there. Ugh. How I agonized over the itinerary. I might look this weekend to see if there's anything open in the beginning of the week. That explains the crazy hi price on the 23rd and the lack of availability in the hotels. That will teach me to check for large events before planning travel. I was just put off by the escalating airfare the further into June I looked, so opted to do the sightseeing before my class.

We had bit of unusually high rate of inflation for couple of years.

Most travel books are printed a year before the year listed on them and are researched even more in advance.

So they tend to be outdated fresh out on stands.

Lisbon is very compact. Most Bolt rides from business area hotels (check out Saldanha for example) to tourists areas are no more than 4-6 euros with advantage of getting dropped of on desired top of the hill.

For example, get dropped of at Miradouro Alcantara fur RS Chiado walk and eliminate wait for Gloria funicular or to top of Castello to start Alfama walk.