Arriving in Toledo on Monday

The walk to the Bisagra gate is about a mile from the station. From it you walk up the hill into the historic center. A little closer, but not by much, to the train station is the Remonte mecánico de Safont / escalator. There’s another escalator just past the Bisagra gate.

Our last two visits to Toledo we stayed at Hotel María Cristina. It isn’t in the historic center, but an easy walk to it. Its address is C. Marqués de Mendigorría, 1. For an upcoming trip we’re staying at the Parador a couple miles outside of town with fantastic views of it. We’ve always had a rental car.

My mom and I enjoyed our stay at Hotel Santa Isabel as recommended by RS back in 2015.

I had reserved a room with a view of the cathedral which was great!

However, our room was on the 3rd floor and just above it there’s a roof terrace. There appears to be no insulation between these two areas so we could hear the metal chairs being dragged on the terrace above us and it made it difficult to fall asleep.
I called the front desk and requested another room but had to wait till the following day when we were moved to the second floor which was nice and quiet.

FYI, the Toledo Cathedral is open on Mondays.

Toledo is very popular, and gets very crowded with day trippers, so I’d presume most places to eat are open on Mondays.

Toledo is one of my favorite cities in Spain, enjoy!

Edited to add..,
We took a taxi to our hotel, since my mom was 88 at the time, but you can take a public bus from the train station to Plaza de Zocodover.

I also stayed at Hotel Santa Isabel last year. It was quaint and centrally located. I took a taxi from the train station and it was worth it. The center of town was a fairly steep uphill ride from the station and the street layouts are pretty confusing. I wouldn't have easily found my hotel. Save your walking for to the sights. The first day I took the tourist sightseeing mini train and enjoyed getting a grand tour of the town. I liked the Army Museum, which included preserved ruins of the historic Alcazar. You can take an elevator to the top of one of the towers there and see the town from above.

Muchos Gracias!

I am thinking of splurging on lunch at a restaurant across the river, at the vista point with the panoramic view. Where should I go? The two choices are:

Restaurante La Ermitaña / Mirador Gastronómico de Toledo

Hotel restaurant at Parador de Toledo

I’d go to the Parador as it sits on a higher hill. There are a number of photos online of the view from it.

Thank you again.

I discover a new issue: I check out at the hotel in Madrid at 11am, but the check-in time at the place in Toledo is 15:00. It's an apartment and therefore there is no luggage storage. (The hotels mentioned above are not available.) How shall I kill 4 hours? About 1.5 hours will be taken by transit from Madrid to Toledo.

One possibility is to make a reservation for lunch at the Parador on my arrival day. Then, I will take a taxi to the Parador from Toledo train station, have an enjoyable lunch, and then check in at the apartment.

We stayed here: https://www.laposadademanolo.com/en/ ....... couldn't have been happier. Good breakfast, location. Nice price Brad

Since you have to wait till 3pm to check into your apartment, I was going to suggest you visit the cathedral and/or the Santa Cruz Museum both of which are open on Monday.

Having said this, I don’t know their policy for letting you in with your luggage.
If your luggage is small, you may be able to visit these sites, otherwise just wonder around the narrow medieval streets and check out the many shops.

I have had some success with contacting the apartment owner/manager, describing my situation, and asking if it might be possible to enter earlier. It's worth a try.