Flight
We suggest you book your flight as soon as you can. Typically at least 9+ months in advance is recommended for the best deal. "Lakeside" or "Piques" Travel Agency are local agencies that can help (possibly those not located in MA, too!) Websites like GoogleFlights, Hotwire.com and Orbitz.com are also very helpful with comparing dates/prices.
House Or Rental
One option to check out places to stay is Airbnb.com. We have used this many times and you can almost always find an affordable place in just about any city! Pro Tip: Look for "Superhosts". Those are hosts with the best reviews and can even have an in-person verification from AirBnB themselves.
Hotel
The main city of Ponta Delgada will likely have the best selection of hotels for our wedding, but you can also stay in hotels in smaller towns closer to Vila Franca (where we will be getting married!) Here are a few of our favorites: 1. Hotel Terra Nosta: http://terranostragardenhotel.com/ 2. Furnas Lake Villas: https://www.furnaslakevillas.pt/ 3. Azor Hotel: http://www.azorhotel.com/en/home
Rental Car
Rental cars should start becoming available around July/August of 2019. Many popular companies in the US have a location in Sao Miguel, so choose one that works for you!