While Portland has it's own small airport, Portland International Jetport, the cheapest option for most people will be to fly into Logan Airport in Boston. Portland is a two hour drive (sometimes slightly longer if it is a Friday in the summer due to tourist travel). If renting a car is not for you, there is an easy, comfortable bus you can pick up straight from the airport via Concord Coachlines. They provide movies, free pretzels, and every bus driver has a thick New England accent. Portland does have Uber and Lyft.
www.vrbo.com and www.airbnb.com are other (possibly cheaper) options to look into as well. Downtown Portland is a known foodie area and has many great restaurants, pubs, and breweries!