Chris, here are the towns/places we hit on the Rota (2016 prices). I had to consult my logbooks, and now I'm super jealous that you're going on this trip - We loved it! If you haven't already, you should get the official guidebook. Hopefully, by now, they have a south to north version (they didn't when we went), but if not it's still a very good guide.
Sagres - Hotel Memmo Baleeira 90€ Very nice; we needed it after a long plane trip. Great breakfast.
Vila do Bispo - Flor de Esteva 50€ Nice, basic accommodation with friendly owners.
Carrapateira – Had a reservation, couldn’t find it, wound up staying in a place a woman we passed in the street had available.
Arrifana - Arrifana Retreat 40€ Definitely recommended. Super hosts (Hi, Kate and Stimpy!). Bonus: You can do laundry here (for 3€, but worth it.) Great places to eat in town.
Aljezur - Jo House 45€ Nothing special. Probably better places that are cheaper.
Odeceixe - Casa Morais 33.60€ It’s like staying at Grandma’s! Literally run by a grandmother, it’s as neat as a pin, and she served up a great breakfast.
Zambujeira do Mar - Camping Villa Park 35€ On the outskirts, but nice. As I recall, not many places to choose from. New swimming pool – I know because they started demoing the old one the morning we left.
Almograve - Pousadas de Juventude 28€ Doesn’t get more basic than this.
Vila Nova de Milfontes - Apartamentos Atlantico 22€ Not sure why we chose this one. It’s nice and was near the water, though, and the price was right. They do laundry.
Porto Covo – Ahoy Porto Covo Hostel 34.50€ Nice enough, although pretty basic.
We skipped the final two legs of the Rota because it headed inland and we felt we’d already seen enough of that. Besides, we needed to save a couple of days so we could spend some time in Lisbon, which I highly recommend.
We took a train to Cascais, then hiked to Sintra (well worth seeing), Silveira, Areia Branca, and Peniche. We took a bus to Obidos, then hiked to Nazare, Sao Pedro de Moel, Coimbra (recommend spending at least two days there), Mealhada, Agueda, and Albergaria-a-Velho.
We caught another bus to Porto (the guidebook made walking into Porto sound less than optimal), then hiked to the Portuguese to Santiago. Porto is another town I recommend spending several days in. Also highly recommend taking the coastal route out of Porto – it’s very different from the Rota, but we liked it a lot.
If you’re interested, I can provide additional information on any of these places/routes.