I live in hotels 20-30% of the year as a “digital nomad”.
Normally that would be a super expensive thing to do, but I got all the hacks to make it cheap and a ton of fun.
Tip: get status
Status is super important in making hotels a whole lot more worth it, and way more fun.
I am currently titanium with Marriott and Diamond with Hilton for reference. There are lots of ways to get status, the first is the hardest part: spending the nights.
The Marriott card is essential as well, you will get 15 nights knocked out just from that. I break down my favorite credit cards as well here
Marriott's loyalty program is better than Hiltons in my opinion. Hiltons diamond status you can essentially buy with this credit card:
The main things you get with status are free suite upgrades, free breakfast, lounge access when there is a lounge, and with Marriott- 4 pm checkout.
When checking in, never go to the honors check-in. The people working those desks are audited on how many people they give upgrades to and are less likely to hook you up.
There are lots of ways to approach the upgrade. You almost always need to ask for it, don’t assume they will give it to you. I like to start with “I see you guys have some suites available, I would love an upgrade with my Titanium status” Now you need to go and check if they are available, and try to add multiple suites to your cart on the Marriott or Hilton. As you are telling them this, show them this screenshot or cart.
The reason is, a lot of times they will tell you they don’t have any available so you are making it harder for them to make an excuse. If they say the site is wrong and they don’t have any available, you can ask them to please double-check and ask the manager.
This lets them save face if they give you one in the end. They just had to “double-check”. You can also tell them you are going to leave an awesome review mentioning their name specifically. That looks great in their bosses’ eyes and gives them more incentive to throw you an upgrade.
Another thing you can say is that you don’t need late checkout (if that is true). There might be a suite available but that has someone checking in the next day. If they give you the room in that case but you have status, they don’t have time to turn the room if you’re there till 4. So this gives them more options.
And of course, just be nice, smile, and make them want to upgrade you.
Become friends with an employee! Both Marriott and Hilton have friends and family programs. Marriott will get you nice discounts last minute if you get added to a friend and family. At Hilton, you’ll get about 50% off rooms which is huge, no last minute needed.
So now you’re getting free breakfast, free lounge+ apps and drinks, and suite upgrades for a fraction of the cheapest room.
Status matching!
So you can also use a status match challenge to get your status. I used my Marriott status and submitted a match request to Hilton. You can’t always do this, but Hilton was running the challenge. You had to do 12 nights within 3 months, and they gave you a diamond for the next 18 months. This allowed me to skip all that time and go straight to it.
Booking direct vs through a deal site:
You are less likely to get upgrades and stuff when not booking direct, but it’s still worth it if you are saving a bunch! Just call the hotel and tell them you want to add your rewards number to your reservation.
Marriott cancellation: if you have status and the cancellation period is over. (Let’s say it’s free cancellation 3 days before check-in and it’s the night before) call up the hotline for your status and ask if they can grant you a complimentary cancellation. Works almost every time.
