Yes, it's possible, but a multi-step process. Generally speaking, you'll want to insert your products first, then insert the product price book entries. You can use the "success" file to match the products to their prices, then simply add a column for the price book ID.
Basically, your file should look like this:
Product Name | Product Code | Description | Family | Price | Price Book
-------------+--------------+-------------+--------+-------+-----------------
Product 1 | 1111 | Words | Fam A | 100 | PricebookIdHere
Product 2 | 2222 | Words | Fam B | 200 | PricebookIdHere
Product 3 | 3333 | Words | Fam C | 300 | PricebookIdHere
Once you import the products, you'll end up with:
Id | Product Name | Product Code | Description | Family | Price | Price Book
---+--------------+--------------+-------------+--------+-------+-----------------
1 | Product 1 | 1111 | Words | Fam A | 100 | PricebookIdHere
2 | Product 2 | 2222 | Words | Fam B | 200 | PricebookIdHere
3 | Product 3 | 3333 | Words | Fam C | 300 | PricebookIdHere
Where 1, 2, and 3 are Salesforce IDs (abbreviated for brevity).
Simply take that success file, then insert the price book entries.
As for inserting new quotes, you might also need to insert additional records, like accounts, contacts, opportunities, etc. You basically just need to insert them in order.