Looking for accommodations in Montepulciano

I've stayed at Meuble il Riccio and really enjoyed it. It's near the top of town close to Piazza Grande, and they may have a nearby free parking spot available. Breakfast is extra, and I usually don't go for breakfasts that cost extra, but theirs is outstanding and well worth the price.

Albergo Duomo

On such short notice, you may not find anything in or near the city center. Montepulciano is oblong shaped, location really can matter to visitors, especially those with a car. There is a learning curve to driving up near the center. Parking can be an issue, too.

I don't leave Italy until Nov 1. So I'm flexible on any day. Driving is a piece of cake for me. Done it many times in many places

I feel comfortable driving in Italy, too. But Montepulciano is a bit unique.

Since most hotels might be booked in the next few weeks, you may want to look at Airbnb. Also try Appartamenti al Poggiolo. They sometimes offer less than 7-night stays at the last minute if they have openings. They have a great parking space within the ZTL, and they call your car info in.

I'm looking at La Terrazza di Montepulciano for the place to stay for a few nights

If La Terrazza has availability and offers parking, it's a fine choice. I prefer the views on the other side of town, but you can drive or walk there.

We stayed here a few years ago and it remains one of my most favorite hotel experiences. Gorgeous views, well located, warm and friendly... and the food, omg.https://www.tripadvisor.com/Hotel_Review-g194833-d1412375-Reviews-Osteria_del_Borgo-Montepulciano_Tuscany.html . You are also literally across the street from Strada del Vino Nobile di Montepulciano which will help you set up tours (we did 2 great small winery tours with them.) and around the corner from FATTORIA DELLA TALOSA where the cellars date back to the 16th century, you can do tastings of their wine as well as buy some lovely Vino Nobile di Montepulciano.

Osteria del Borgo has a great location and some lovely accommodations. They offer the view I prefer most. You also have the convenience of their popular restaurant. I don't think they offer free parking. The closest lot is a small distance away, but it can get filled quickly during busy hours.