Unfortunately, the Hertz underage fee waiver is only valid through 5/31, and it appears they have not (yet) extended it past that date (even though they usually do keep it running).

Here's Hertz for $310.31 using the Gold Family CDP, which has been reported in years past to waive the underage fee. However, I'm not seeing any current discussion on FlyerTalk about this code, and references to it seem to have been removed from the Hertz site, so we can't guarantee that it will waive the fee.

FWIW, the best rate we found was $264.91, but we couldn't use that rate and still get your underage fee waived, so you'd end up spending more.

Our system isn't currently set up to factor in underage driver fee waivers, so this is the result of some manual-assisted searching, and someone with a lot of patience may be able to find a better deal than we were able to.

Same caveats as above. Here's Hertz for $85.89 with the Gold Family discount, which should waive the underage fee.

Here are two other options. Alamo at $46.04 has a $35/day underage fee, and Enterprise at $62.89 has a $15/day underage fee. Hertz will still work out cheaper if that CDP still waives the underage fee, but we just wanted to give you some other options.

Those questions are probably best asked in their respective forums for a comprehensive answer from other experienced travelers.

Generally, as a basic Hertz Gold or Avis Preferred member, you shouldn't expect a free upgrade.

There's a decent chance of getting something a bit nicer in National's Emerald Aisle. You may want to take a look at recent posts in the "Cars at SJC" thread in the National forum for some reports that might give you an idea what to expect in the Emerald Aisle if you book a midsize.

Wow...sometimes you find that a discount code only drops a few percent off, and sometimes you find it drops the rate (with no rhyme or reason) over 80%. This is one of the latter situations. Check here to watch a $2,102 rate with Budget drop down to $370.64.

And just to stay on-topic for this thread, you can see Hertz being very competitive with a $1,902 rate.

Hertz, if you like, or save a hundred bucks and go for another company.

A gentle reminder: it helps us process your request faster if you can post the ZIP code for pick-up.

Several companies (like Hertz and Avis) do not typically charge drop fees. Instead, when you book a one-way rental, they simply raise their base rate, thus bundling the drop fee in the rate itself rather than listing it separately. Other companies, like Dollar, charge the same base rate for a local or one-way reservation but then tack on a drop fee. Regardless, as long as your reservation specifies the pick-up and drop-off locations, your quote is valid and you won't be charged anything extra.

We found as low as $184.86 with Budget. That is so much lower than the other companies that it's best to go with that quote, even if you have to pay the underage fee (Hertz with the Gold Family CDP is $300 more, and you'll only pay about $135 in underage fees).

We love seeing $6,000 rates drop by almost $5,000 with a simple application of a discount code. Sometimes we're not sure if the rental agencies even know what their own codes are capable of.

Here's $1,304 with National. Hertz isn't even worth mentioning at $3,222.

Apologies for missing your request.

For that long of a rental, you may be better off buying a car and re-selling it at the end of the term.

I checked, and our system wasn't able to find any off-airport rates for that long of a rental. We could break it down into 6 one-month rentals and search for and book them that way. Rates at BOS (airport) are available; best we found was $4716.31 with Budget or about $40 more for Avis (something I would do, as Avis would likely provide much better service along the way if something happens to the car).

If you found $3300, maybe you could share where you found that rate and we can use that info to try to help refine the result and maybe convince our system to search for further discounts on it.