How did you choose your accomodations?

For me, it's always the place and what draws me to it. The choice of accommodation boils down to the cost, access to public transportation, walking distances, and food. I balance these items, giving and taking, and pick the best option. Most often, I am satisfied.

We work out our itinerary first, then we book accommodations.

When I'm planning, I keep in mind the things that we really value in an accommodation.

A location near the city center.

Excellent WiFi.

Decide hotel or apartment. If apartment, preferred amenities? Coffee maker, washing machine, etc.

Excellent ratings - look at the lowest and highest. We prefer a quiet place, comfortable bed, etc.

I start with Booking.com to review options, compare prices with the places I'm interested in and go from there.

I use Google Maps to check the location based on the address to see if restaurants and sights that we might want to visit are nearby. Also, the location of public transportation and also for you, parking availability as you'll have a car.

Once I chose a place, I compare Booking.com price to the direct booking price and if it makes sense, I book direct.

It's a lot to consider but spending time to find a place to stay that meets your needs will make your travels more enjoyable!

As for location, I also use street view of goggle maps - and drive around a bit to see if I like the area, the feel - so I know if I will enjoy walking around! And for me, lobby and breakfast rooms are important - I always look close at those as I want to sit and enjoy a bit with coffee, write in a journal, etc.

In recent years, I've added Google Earth to my vetting procedure before choosing an accommodation.

Case in point: I was about to book an Airbnb in a small seaside town in Italy, and the listing said the apartment was just "steps away" from the bus stop. Well, that sounded good.

But then when I Google Earthed it, I saw that the apartment was way up a hill from the street level, and the "few steps" was a steep winding, stone staircase with a handrail only on one side. We are seniors and carrying our own luggage so NO, that isn't going to work for us! None of the photos in the listing showed it from the perspective I saw when I did the Street Image on Google Earth.

I learned this lesson the hard way from an earlier trip where I booked an Airbnb in a small town in France. Again, it was described as being a "short walk" or an "easy taxi ride" from the train station. I even messaged the host to verify this and she assured me we could get a taxi, no problem.

Well, when we arrived - on a day POURING DOWN rain - there was no taxi stand at the station and no Uber service in town. I contacted the host who informed me that I was supposed to arrange ahead of time for a taxi to come from a nearby town. (But of course she didn't bother to tell me that when I had specifically inquired about it.)

We ended up walking over a mile in the pouring rain and the last half mile was straight uphill. As senior citizens toting our luggage, and walking uphill in the rain, we weren't happy campers. A quick search on Google Earth would have sussed out the distance and terrain, at least.

So while everyone's criteria is different, my concern is always how easy it is to get to the accommodations, whether taxi service is available, and what kind of terrain we can expect. Since you'll have a car, it might be important to find out if there is parking available and/or if the accommodations are located in a vehicle restricted zone.

A few years ago we stayed at a lovely townhouse in Cortona, which is in Tuscany but on the border with Umbria. We rented through Together in Tuscany and were very, very happy with the location, accommodation and access to all we wanted to do and see. It was in the center of Cortona so easy evenings to dinner, gelato or a stroll. Easy, free parking outside old town walls. A charming town that we all loved. Just a suggestion for you as you plan your trip.

Accommodations can make (or break) a trip for me- so I first come up with my priorities. Air conditioning, wifi, a pool, on site food, free breakfast, or whatnot. As well as what I want to be walkable (easily) such as a grocery store or near a pharmacy etc.

I also note on Google Maps my restaurant and sites to visit so I can visually see how easy it’ll be getting to food and activities from where I’d possibly stay

I also use Google Maps to look around at street level and see what does it look like? What is around (and behind) the hotel? Does it look like it’s a party zone? Loud bars? Gardens and residential quiet?

I also look at public transportation as we almost never rent a car

So usually, the accommodations get finalized once the trip is decently planned ensuring I know what will serve us on that trip.

Agree with Kimberley - we stayed in Cortona for three months inside the walled area, and just loved walking around the town. Some steep inclines, though, but I still made mass up them a few times! Taxi ride to Camucia where you catch the train anywhere. We had a car (buy/buy back) and drove through Tuscany!

We choose hotel somewhat near the sites we’ll be visiting. With a rental car a hotel with onsite parking is a major factor. After that, a hotel with charm, possibly some age to it, and not a chain hotel.

We tend to have a general idea of our route and places we want to visit prior to making hotel reservations.

We do look at reviews. Through them we are able to eliminate a number of places.

As I move from hotel to hotel, I am somewhat picky and need a few things.

I start with the city/town I want to visit.

Then I look at reviews on both TripAdvisor and Booking. i start with the highest rated hotels and go down the list.

I'm looking for:
--location within the city. Is there public transportation nearby.

--cost in comparison to other properties and to my budget.

--noise reports. I like quiet and if reviewers complain about noise I move on to the next hotel.

--cleanliness.

--amenities such as a/c, kettle/coffeemaker, refrigerator, good wifi,
laundry room. Depending on the length of the stay I may look for an aparthotel.

--I lean towards chains as I play the points game.I give up charm--in some cases--for future free rooms.

--when I think a hotel may be right, I then look at a map to see if there is anything nearby that could cause problems.

I then book directly with the hotel or with the chain if a chain hotel.

I prefer hotels over apartments.

Deb, if its Umbrian choices you are after, then we'd recco Spoleto-based real estate agent Luana Zingarelli. We once rented an excellent double-apartment through her company 'Italy to Rent'. That apartment was owned by a friendly Foligno family and overlooked the attractive main square in Bevagna.
Whenever possible nowadays, we try to cut out the middlemen/agencies such as VRBO or booking.com. No easy task but still...
Good luck and tante belle cose.
I am done. the end

I guess if you are considering a farm stay what is the reason for that versus a small hotel or other accommodation in the small towns- are you looking to relax at the farm stay and view the farms/ rural-ish setting and a "rustic" accommodation" - I'm only guessing on what and how an Italian farm stay accommodation is set up decorated. If that is the case then foucs on that when searching. What else is in the area? How easy is it to go for a leisurely walk in the area?

This isn't specific to Italy:
Usually I'm in a larger town and I'm using public transport to get from place to place. So I want to be in a central area. I look for a hotel in a central area of the city that is near to some of the sights I want to see. It needs to be clean and have good reviews on the various sites. It needs to have wi-fi and ideally breakfast. Of course I factor in the cost. I don't need 5 star accommodations. I'm out and about all day so it only needs to be good for sleeping and a few hours in the evening once I've wrapped up my sight seeing for the day.

I suggest longer stays with fewer locations.

When we went to Chianti, we wanted a central location within an hour’s drive of the home base. Though we had a rental car, we wanted something on the bus line so we could get to Florence without the car. We chose an Agri turismo winery near Greece and it was ideal. We booked direct.

We’ll be in Umbria in October and will use Perugia as a home base. We’ll spend part of the time at an Agri turismo where we’ll help harvest olives and take cooking classes. We’ll also spend three days in Florence. It will be all public transportation and everything is booked.

We were in Tuscany this May. Like you we had many of the same criteria. Initially we were looking for an agriturismo with meals, but ended up in one with a small kitchen. We ended up making our own breakfast and dinners, saving money. We ate large midday meals while exploring the small towns and countryside.
I chose agriturismos that met were smaller, had character and great reviews. Then my husband and I
compared the choices and my narrowed it down. I know that planning so far ahead you have many options.

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I agree with most everything said here! I always prioritize location/neighborhood, breakfast being included (a must for us) and wifi. I also appreciate having fresh air and good light in our room via windows, a balcony, terrace or outdoor space. I book with locally owned bed and breakfasts or small hotels. I use several resources Ric Steves first, Trip advisor second possibly and booking.com to scroll thru tons of reviews for insider comments. It has proven to be very helpful. We are headed to Italy for 5 weeks of travel and have booked Agriturismo il Segeto di Pietrafitta just outside of San Gimignano for several nights. We are taking dinners there after ‘day tripping’ based on their outstanding reviews and appreciate the fact that we can dine, drink wine with our dinner and stumble into bed without having to do any more driving. Have a great time!
www.ilsegretodipietrafitta.com

I choose the location first, then look for accommodations in the area.
I usually have a car, therefore I try to find accommodations with parking arrangements of that sort (not necessarily free parking, but available parking). Some (most) towns have traffic restrictions in the historical center (called ZTL or Zona Traffico Limitato), therefore I select accommodations outside of the traffic restricted area, but close enough to the center that I can walk. Taxicabs are outrageously expensive in Italy, and not even available much in smaller towns, so I don't rely on taxicabs at all.
Sometimes I'm not walking distance from the core of the town, but I don't mind a short drive to a parking lot at the city center (but outside the ZTL). If you prefer farm stay, choose one that is not in the boondocks and/or provides some sort of restaurant service, because those tend to be far from towns, so they might require a lot of driving.