When you are not the indoor type of person, the best time to visit would be around June to August. It is during these months that the city sees warmer weather. As such, you would also have enough opportunities to be outdoors. During these months, you would also be seeing a lot of roses bloom in the city. The city has an International Rose Garden that is one for the books. You should never miss it. It’s in full bloom during these months. Because of such reasons, these months are also the city’s peak months. When you plan to go on vacation in Portland in Oregon during these months, it would be wise to book ahead. To ensure you have the best rooms and the best rates, book about two months ahead. If you do not mind the weather, you can go during winter. The hotels are way cheaper during this time. The weather is chilly. And when you are into winter sports, the city sits near Mount Hood. This gives you a lot of opportunities for such activities. No matter what time of the year you want to visit, there is always something for you. It is a matter of personal preference. If you are the outdoorsy type of person, go with summer. If you prefer winter sports or hate the crowds, visit during winter.