Although people travel in different ways, I typically try to use miles and points for most of our travel, and try to avoid paying cash for things. Our point earning to travel time ratio is high enough that this has been a manageable solution for us. One downside is that using points to book a hotel room almost always gets you a “standard” room with not any options to use points to get anything different, although some hotels during the most recent Point Breaks sale DID book into suites or premium rooms (it’s usually up to the particular hotel)
I personally haven’t put a ton of value in getting elite status, although I did status match to Hilton Diamond (but NOT Hyatt Diamond!) and have various statuses through credit cards. What that means is when I book a hotel room, I don’t get a ton of free upgrades (though sometimes it works out). 
Booking a night in Orlando
For our family of 8, booking hotels is a little tricky. In most cases we require 2 rooms (just like we’re a 2 car rental family), but there are some suites and larger rooms that will fit our entire family. For a possible upcoming trip, one hotel that we were looking at the Staybridge Suites Lake Buena Vista near Orlando, where the nightly point rate is 35,000 points / night, which only books into a standard 1 bedroom suite. I’ve had success in trying to get upgrades at Homewood Suites hotels (Hilton) before, so I thought I would email the hotel to see if there were any options to get into a 2 bedroom suite.
Here was their response:
Thank you so much for being an IHG Platinum member. We do appreciate your loyalty.Using your points will only allow you to book a one-bedroom suite. However, at our property, we can upgrade you to a 2 bedroom at a rate of $45.00 per night, provided we have availability. If our property is your desired location, you can contact IHG Rewards and book the reservation using points and then call me and I’ll do the upgrade.Thanks again and I hope to hear from you soon
Never take the first offer!
Of course I have a problem paying for ANYTHING, and even though $45 in lieu of having to spend 35,000 additional points seemed like a pretty good deal, I thought I’d try to negotiate a little bit. I looked at the room availability for the dates in question
Like we talked about, a points booking will book into the standard 1 bedroom suite. But in this case, you can see that the 2 bedroom suite (that sleeps 8) is only $10.80 more! I replied back to the hotel and asked if they would be willing to upgrade the booking for only the price difference, and they agreed!
Hope this helps you if you’re looking to book anything besides the “standard” room – you may be able to upgrade your room for a fairly reasonable. While I understand that not many other travelers require 2 rooms like we do, you can also use this trick to upgrade into a Club or Executive room. Some chains (such as Hyatt and SPG) actually have a standard award chart to use points to either book or upgrade into a premium room.
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Dan Miller travels with his wife and 6 (SIX!) children. He loves to help families travel for free / cheap, especially larger families. If you are looking for help, drop him an email at 
Thanks Dan. Good info. We need an upgrade for our family of 4 just for the space as well. I will try asking. I’m assuming it’ll be a negative considering it’ll be both Westin Maui & St Regis Dana Point this summer (high season) but never hurts to ask!
I took your idea and tried to apply it at Holiday Inn Express Madison Square Garden. In this case, it for valet parking. Here’s the situation. I booked one reward night (April 10) for 35,000 points. As I will drive at park at the hotel, the valet parking at the hotel is $55 USD. I checked IHG’s reservation for the same night (April 10), with a standard room (equivalent to my reward redemption), it’s at $329. There is also another option for this standard room which includes valet parking, this is at $354. So I emailed to hotel directly asking if they would consider offering me with valet parking at $25 (which is the difference between $354 and $329), instead of having to pay $55 USD for valet parking.
Here is an extract of my email to Holiday Inn Express MSG:
“…I notice on IHG’s reservation, for the same night and for an equivalent room to my reward redemption, it’s at $329 and there is also an option with valet parking at $354. So would it be possible to include valet parking with my reward reservation for an additional $25 USD ($354-$329) instead of $55 USD if paid separately?”.
The email response from the hotel staff is:
“Thank you for choosing to stay with us. Unfortunately with an award night reservation we can not offer the valet service as a package. The valet would be separate and it is $55.00 + tax per night for a standard size vehicle.”.
Oh well…
That’s a bummer! I’ve had success in getting parking charges waived when staying on points, but it is dependent on the hotel
Thanks Dan….I’ll ask the front desk staff to consider waiving the (very stiff) parking fee upon check-in. Would you share how you manage to get parking charges waived when staying on points?
Canh.
Nothing magical – I just called the hotel. They said that in order for me to leave my car there, I had to book the park and ride rate. I told them I was staying on points and they agreed to not charge extra for parking. Probably depends on the hotel, who you speak with, and how they’re feeling that day…
Thanks. I’ll give it one more try. And will report back afterward.