Always deals on Booking.com sometimes you don’t have to pay a deposit. I’m using them again this November. Here is my affiliate link so check out some deals! You usually pay at the hotel with Booking.com. Some hotels require a deposit up front and remaining 30 days before your trip. I stayed at Staypineapple at Hotel Rose back in May 2019. Great boutique hotel with comfortable beds. Restaurant had good food as well, good location. I took tours so they picked me up everyday from hotel. I booked my tours with viator the entire time I was in Portland.