I typically book direct with the lodging in the USA. I was advised that using a booking service, smooths out the language translation and also payment. Thus, all of our reservations this trip were made through booking.com except for a couple of small places that took deeper searching to find lodging.

At home, I prefer lodging on route, good reviews, near food, fridge/microwave, bike in the room, and a substantial breakfast. I've been told that the last three things on my list are not usually done in Europe. I am not a good tourist. I love to ride my bicycle, then take a shower, and relax in the room. This trip I'm going to make an effort to see the sites, so I factored closeness to castles, aqueducts, etc into my decision making.

MADRID - Hostal Viky. Less expensive, free airport shuttle, close to a friendly bike shop, and the Barajas Plaza. We want to exit to the north, so we wanted to stay in this area. The room is very small, but clean. The walls are paper thin. I could hear the neighbor's alarm clock this morning. We woke up even earlier than their alarm, but tried to talk quietly. Based only on the privacy issues, I looked again for more lodging. There were a couple more choices, but they didn't advertise a shuttle, were more expensive, and from the photos, had a similar style of room. Poor wifi, very small TV. 164E for two nights. 

MIRAFLORES DE LA SIERRA - El Encanto has three domiciles. We have an apartment on the top floor. It is spacious, with an efficiency kitchen, with a washer! There is no AC, that was an error on my part, and no fan either. The windows are all open for a cross breeze.  Poor wi-fi, very small TV. 70E, an excellent price.

LOZOYA - Ciclo Lodge is worth a look just to see the common rooms' decorations. Bicycles are in their own private rooms in the garage. Our room key also opens our bicycles' room! The room itself is modest. No AC, fan only (it's warm). Reasonably good wi-fi. No TV. No fridge or microwave. Probably I should note those only if we have them, as they don't seem common. There's also a restaurant on site, that opens at 8 PM. They are open for breakfast at 8 AM. This was the only place available when I was booking the trip. Jacinto said there were several lodging spots in town. There is also a campground outside of town at the Rio Lozyoa (which sure looks like a lake or a dam to me). 150 E. 

Segovia - San Antonio Motel. This was an upscale choice for us, but we wanted to be close to the sights. There were two weddings the day we arrived. It was a nicer place. Bonus for us is that they had a breakfast buffet. We were instructed to put our bikes in the room. Hurray! They even had ice, although there was some puzzlement from the attendant that we wanted a full cup of ice. The big negative, and it was so negative that I might not suggest staying there again was that the internet was so poor that I couldn't load even one photo. Our room was closest to the office, I would think that we should have had good service. 227 E for two nights.

Medina del Campo - Hotel Villa de Ferias. We have a fridge in our room for the first time. Clean, double beds. Roomy bathroom. They have what seems to be the typically difficult bathtub to get in. Just saying that makes me feel old! The bottoms are sloped, and they don't have shower curtains, but a solid plexiglass (?) divider that makes it hard to enter the tub. The rooms are above the cafe, which was a little noisy at night with people on the patio. Our room had weak AC. Good internet. 81 E

Toro - Hotel Juan II - Bikes in the banquet room. Breakfast buffet is available for 9.80E. Our room is larger. We have a queen size bed, and one pillow that goes from side to side. Sleeping tonight will be interesting! We have a terrace with an amazing view. TV, no fridge. Instant coffee in the room. There's a restaurant/bar downstairs that we haven't visited. It is worth staying here for the view alone. The Alcazar is right next door. 83E.

Zamora - Palacio Del Duero. Super friendly check in lady. She got me a champagne bucket of ice! Bikes in a locked, covered courtyard area. Upscale, roomy, four pillows on the king size bed. Breakfast buffet for 13E. 122E

Ledesma - Hotel Rural el Rocal. To be fair, the check in lady was doing it all, but she sure wasn’t friendly in her efficiency.  Bikes went in an unused stairwell. Our room was clean, and recently updated with exposed brick accents. The bathroom had a walk in shower, no risking life and limb this time. Big negative was the AC made noises, but didn’t blow. They gave us a poorly working little fan. The sun was on our terrace until 10 PM. Then it cooled off nicely. We were over the restaurant/bar, but it was quiet. There are other choices in town. 

La Alberca - Hotel Las Batuecas - right on the main drag. Bikes were allowed in the room, but mine would fit upstairs. We had a fridge! The AC worked. Roomy studio apartment with living room furniture. The bed was a little tired. The shower was extremely small. Good WiFi. Ice when asked. It will be 105 degrees today. Ice is important! We would stay here again. 100 E

Moraleja - Hotel Delphos - Very basic room in a town that you go through to get somewhere else. The owner (?) was most kind and helpful. We ate several meals at the downstairs restaurant. I would stay here again, but don't expect more than clean and serviceable. 40 E. At least the price was cheap.

Vila Velha de Ródão - Vila Portuguesa - we had a walkout downstairs suite with a kitchen and TWO AC units. The wi-fi was good. It's a wonder we ever left! 100E

Marvao - Dom Dinis - Nice lodging. Our bikes went in the downstairs, outside courtyard and were watered in the morning. Very steep stairs to the room. The AC worked well. 80E

Elvas - Bastion Apartments - Nice studio apartment with a kitchen. Good AC and wi-fi. Jacinto commented several times on the nice bed. I thought it was average. Extra nice bathroom. Good location. We couldn't get in until 4 PM, and they had an app we had to use to enter the apartment. It was difficult to use and slightly stressful. 216E for two nights.

Monsaraz - Casa Pinto - downstairs apartment next to the office. Good wi-fi. AC is a portable unit that is vented to the outside. It's tolerable in the living room. Bedtime might not be as nice. The bathroom is extra fancy. Bikes in the reception area, although I think they would have gone fine in the apartment.  They didn't unlock the front door until 3 PM to get in. 109E

Serpa - Hotel Beatriz. Nice check in ladies. Medium internet, I had to go to the office to load photos. Bikes in an outdoor locked courtyard. Good breakfast included. Smallish room, but nice. Good AC. If you stay here, make sure you go to the hotel and not the apartments, just down the block! Good value for the money. 59E 

Mertola - Hotel Museo. Nice check in ladies. Bikes in the handicap bathroom. Excellent buffet breakfast for 7.50E. Good internet. Nice room. Good internet. AC good. Swimming pool. 75E

Alosno - Convento Hermana Esther. Very cold AC. Access to kitchen. Swimming pool. Bikes in a niche next to stairs. Good location, close to food.Beautiful building. Small private patio. 70E.

Almonaster - Casa La Torre - two bedroom house. Two AC units. Very, very nice. Napkins, dish towels, ice. All of the conveniences of home except a clothes washer. Excellent location. If I run away from home, you can find me here. 160.E two nights.

Fregenal de la Sierra - Hotel Cristina. Beautiful old building. Large bedroom. Poor AC. Good internet. Attached restaurant. Included breakfast. Bikes allowed in room if we carry them up stairs. We put them in a conference room instead. 75E.

Jerez de los Caballeros - Hotel Oasis. Friendly, hard working owner. Big hotel with an adjoining restaurant and a disco upstairs. Happily, they have very thick walls. Our bikes went across the street in their garage. Provided breakfast is included, but the nice lady gave us to go boxes. AC was sufficient, as was the wi-fi. We had a comfy loveseat that I wouldn't mind having at home. Queen size bed with one large pillow. We would stay here again. 68 E.

Merida - Petrolina 1881 apartment. A spacious splurge for our day off. Excellent location. Bikes in a storage room downstairs. Two bed/two bath. Kitchen, etc. Very clean and well appointment. Definitely recommended. 330 E two nights.

Trujillo - Hostal San Miguel - bikes in the parking. Wi-fi poor. I had to sit in the common area. Very clean, large room. Interesting building, unusual ceilings, tile floors. Good AC. One big pillow. Breakfast was minimal, late, not included. We didn’t stay. Good location. Good value for the money. 49E

Villarreal de San Carlos-casa Rural El Mirador. Small apartment. Very clean. Good WiFi and AC. One big pillow. Squishy bed. Hostess cooked all of our meals for us, which was a life saver because the two restaurants in town were both closed. Very special location and worth the visit to the park. 80E

Jarandilla de La Vera - Paradore. Just pulling up in the driveway made me feel special. Bikes at the end of the drive (that we just bicycled up!), in a locked garden shed. Spacious room, love seat. Nice bathroom. Good AC and WiFi. Probably not the most bang for your buck,  but, hey, you are sleeping in a castle! 130E

Arenas de San Pedro - Hostal de Castillo - we have a castle view, but are definitely not in the castle! It's a clean, basic room. Wifi and AC. Jacinto's bike is in storage on the second floor, mine is next to the staircase in the entry. The stairs are narrow and twisting. There are a LOT of stairs. Good location and price. 40E. Edit - the walls are very thick in old buildings. We have enjoyed silence the entire trip. Not tonight. We can hear all of our neighbors and also the smoke detector is chirping. We would not stay here again. 

San Martin de Valdeiglesias -  Hotel Labranza - ask for room #1, and enjoy being downstairs! Ten stars to this place for not having stairs. After 43 steep steps last night, this was an extra treat. How was the room? Who cares - it was downstairs! Reality - small room. AC, wifi, and TV all work well. My bicycle is parked under the window outside in a cute courtyard. Breakfast is available for 8.50E, but doesn't start until 9:30. 80E.

Torrelodones - PAX Torrelodones. FRIDGE. Bikes in room. Breakfast for $9.50 each. Wifi and AC are good.  It looks like an upscale hotel, but there's not a single wall decoration in the room, and it feels fairly basic. One pillow per bed. We have a ground floor room. We feel like we scored on many levels, even if the room is a little sparse. Bigger than average room. The bikes fit fine. No extra seating, such as a cushioned chair or loveseat.  100E