Puglia bases near Monopoli and Lecce

I stayed near the station but parked in the street in Lecce a few months ago.
However if you do a search on booking.com using filters for parking etc. you should be able to find plenty for under 300€. For example this one below has parking for 15€ a day and I checked for May and they have availability for less than 150€ a night. And it’s only 10min walk from the city center (Piazza Sant’Oronzo). If you want to visit Lecce I would stay in Lecce. Gallipoli is at least 30-35 min drive away.
https://maps.app.goo.gl/UHjoYurjjYEPr6pW9?g_st=ic

Use the same strategy to find something for Monopoli, or maybe Polignano nearby. Or you can stay anywhere in the area. I stayed near Alberobello at a resort, and from there I visited Polignano, Ostuni, Matera, Locorotondo and more. Those places are not that far from one another and the resort was way less than 300€ in spite being in July.
https://maps.app.goo.gl/vf5ibuM4UUuaKMmi7?g_st=ic

I stayed at Palazzo Indelli in Monopoli last May. It’s a hotel with an elevator and breakfast is served on the ground floor. I remember seeing a parking lot very close, and it’s on a piazza with several restaurants and others nearby. And the bathroom was modern & large shower. I had a room with a nice window looking out at the piazza.

For Lecce, I stayed at B&B, Dimora San Giuseppe. It also has an elevator. My room was huge! And a modern bathroom with a large shower. Breakfast was served on the terrace.

I won’t give you my recommendation for Bari where I’ve stayed twice because the room itself, although very large, is a split level with the bed upstairs & bathroom, seating area and small kitchen are downstairs.

My rooms haven’t been at the €300 range except for my favorite one in Polignano a Mare which is an exceptional place! You should be able to find good options n Booking.com, filtering for your needs & a rating of 8+.

Enjoy your time! I will be back during that time, also.

MASSERIA CAMARDA is a 5-minute drive from Ceglie and about 20 minutes or so from Ostuni. We spent three days there and loved it. Very kind owner, Alex, who is fluent in English. If you stay there, make a reservation ahead of arrival to eat at Cibus, considered one of the best restaurants in Puglia; it's in Ceglie.

https://www.hungryonion.org/t/ceglie-messapica-three-nights-outside-an-untouched-jewel-of-a-town/45394

In Lecce I found a good 2 BR 1 bath AirBnB within walking distance to both the Old Town and the train station. I need it for March 2027 but faux-booked it for March 2026. Very reasonable.

Friends whose opinion I respect said that Bari is too busy, Polignano a Mare is on the verge of being too touristy. My brother stayed off the coast in Manduria and found it charming, but since we won't have a car we're regulated to basing along the train line, which is fine with us.

I have not checked the recent rates, but Roof Barocco Suites in Lecce always helped us out with parking (a garage space on second visit). There is a set of stairs to access it though, as it in indeed on the roof of a home.
http://www.roofbaroccosuite.it/en
In Monopoli I rented through HelloApulia and I am sure paid less for a whole apartment, but I guess prices could have risen that much since.
https://www.helloapulia.com/en/
I also use Booking.com and I am sure you will find something with those parameters. Any of those nearby towns would also be fine.

Polignano a Mare is indeed getting too busy if you’re just planning to go see it during the day. But if you stay there, it’s so special to walk through during the early mornings and in the evening.

Unless you need to stay in Bari for train connections, I would stay in a different town. I stayed there twice for the San Nicola festival and enjoyed the experience because of the purpose. It is a nice contrast, though, if you were staying several places during a few weeks in Puglia.