Hoping to have bases in the above areas for 3-5 days at a time to explore areas leisurely with a car in May. Any masserias, hotels, airbnbs, or VRBOs welcomed, as well as tour guides.

Matera - La Corte dei Pastori
Locorotondo - Masseria Aprile

Masseria Cervarolo is a gorgeous property 6km from Ostuni. ( lots of free parking, great food, very nice staff, lovely rooms) We used it as a base to visit Alberobello, Locorotondo, Martina Franca, etc, all the towns in the valle d'Itria basically, plus we did a day trip to Matera from there. In Matera we used Nadia Garlatti for our guide for the day, she was very good.
In Lecce in 2022 we used Sara Bianchi and she was also great. She is on Instagram as sb_sarabianchi or she also uses the Airbnb platform.
In Lecce we stayed at Palazzo Maresgallo which was just gorgeous, but a splurge and may or may not be in your budget as you didn't say what that was. If you stay in the historic centre of Lecce you may have to park outside the old city or have your hotel valet park your car. From Lecce it is easy to explore some of the towns to the south.

I didn't love where I stayed in Lecce (though Lecce is great), so I'll skip the recs for that.

Matera - enjoyed staying at Hotel Italia, chose a superior (?) room, great view. Breakfast was just okay, but I liked the hotel and its location. Having stayed in a cave hotel in the past, I wanted something above ground in Matera. Many folks don't share this feeling.

In Locorotondo, I loved 1783 Dimora d'Epoca. Beautiful, intimate, wonderful service. (I know, I know, you mentioned Alberobello, but Locorotondo is close.)

I wouldn’t stay in Alberobello rather a different town nearby such as Locorotundo. Alberobello is a huge tourist center, mobbed.

Sharing some of our acco choices from our October 23 travels:
Matera : La Dolce Vita (beautifully restored sassi rooms)
Alberobello : Trullo 100 Passi (unique experience, staying in an independent trulli home, with modern interiors). FYI, Alberobello can get busy during the day (I suspect May will not be too busy anyway), but is magical early morning and at night when you have it all to yourself.
Lecce : La Corte (B&B style acco, on edge of the historic centre)

These suggestions are wonderful. We are on it and will update shortly. Thank you!

We have reserved a lovely room with outdoor patio and kitchen at Messaria Aprile. Thank you. The Lecce recommendation was a little too pricey, but beautiful, yes. We continue to appreciate recommendations for Lecce.

Ttt

I've stayed at Dimora San Giusseppe in Lecce twice and loved it both times!

Was it difficult to visit Lecce from there, as it is in Otranto?

Update: for Matera and Alberobello, we have booked Masseria Aprile in Locorotondo to explore as a base. Our challenge is Lecce, as we are not sure whether to stay inside the historic town or outside in the extended area.

I stayed "inside" but close to the perimeter where I knew there were several parking lots. I found detailed, practical advice about the location of parking lots and spaces right outside the ZTL on the TA Puglia forum. If you don't feel like asking a question there, just do a search--you'll find numerous threads with links, maps, etc.

If possible, I recommend staying in Matera rather than day-tripping there. In Locorotondo, I can recommend Ristorante u'Curdunn - https://www.ucurdunnristorante.it/

VF, here's an excerpt from our TR here titled 'Bella Puglia':

'Lecce— The two ground floor apartments available for rental through Prestige B&B can be combined as one. Owners Renata and Steve will take care of you. Their wonderful upper terrace, part of their actual B&B, is a peaceful respite from the hustle and bustle of the main street below. At night, the terrace is so calming that more than once as staff has arrived at 7am to set up breakfast, they’ve discovered a slumbering guest there collapsed on a chair, empty bottle of wine in hand! Location: next door to noted Church Rosario-Battista (excellent view from above terrace)'
I am done. the end

Dimora San Giuseppe is in the centre of the historic part of Lecce - https://dimorasangiuseppe.com/

It is an easy walk to the train station if you are day-tripping.

Thank you. We will check about this.

We have gotten word from Prestige B & B that we could be there for 4 nights, but the terrace is not open and they no longer serve breakfast. What are your thoughts? Is it a far and/or difficult walk from parking and/or places for breakfast?

Virginia, we are non-drivers so I don't tend to retain 'proximity-to-parking' details. Def not a far walk for self-catering, in fact the proximity to that trio of food places we mention in that TR 'Bella Puglia' (a modest market, a VG pizza place, plus the best supermarket in town *be sure to take a number at its butchery!) is valuable, maybe I dunno, 8-10 mins if that. Breakfast in Lecce...hmmm, I cannot say where for sure but its size hits that sweet spot of 'ain't nuthin' too far that it can't be walked by most regular travelers'.
No breakfast is no biggie at most B&Bs but I wonder wazzup with their new 'no terrace' policy?
Anyway, they are friendly owners and I'm confident that their B&B remains a good choice.

*I'll bet that bilboburgler here would be willing to advise---he and his wife got married in Lecce.
I am done. the end.

Thank you all! We have been involved in a family health crisis, which worked out well, and out of touch. Back to planning now. We booked B&B Prestige in Lecce for 4 nights to explore the "heel".