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Hotels | 1,000+ Nights

I have stayed in hotels for well over 1,000 nights in the past 10 years. According to my Marriott app, I’ve logged 531 nights as of September 2025. In addition, I spent about four years staying in Hiltons for roughly 150 to 200 nights each year, with 2018 alone totaling 222 nights (I kept some records, but their app does not). This doesn’t include nights booked under my wife’s accounts, nearly 100 stays at IHG hotels, or other independent properties. Some of these were five-star resorts or luxury city hotels, but the vast majority were spent at places like Hampton Inn or Residence Inn.

All of this is to say, I have a fair amount of experience sleeping in beds that aren’t my own. I want to share the good, the bad, the really bad, what’s considered “industry standard,” and when it’s worth filing a complaint (and to whom). I’ll also talk about the things that disappoint me most and what I wish the industry would improve. But first, let’s take a quick look at the history of hotels and where the industry stands today.

History

Inns have been around for thousands of years. The concept has likely been around beyond any historical records. They were used for merchants who traveled for business. High in the Swiss Alps, the hospice at the Great St. Bernard Pass has welcomed travelers since the 10th century. Founded by St. Bernard of Montjoux, it continues to be run by Augustinian monks today. My point is that leaving your home and setting out on a journey but needing a place to rest is not a foreign concept.

In the United States, there was a point in time when hotels were only afforded by the rich. The late 1800s defined the Grand Hotel Era. Hotels like The Waldorf in New York City (1893) and Chicago’s Palmer House (1871, rebuilt in 1873 after burning down in the Great Chicago Fire) set the stage. Out west, there was the Hotel del Coronado (San Diego, 1888). These were symbols of wealth during America’s Gilded Age. They were built like castles, with giant chandeliers and marble throughout, and they included innovations such as elevators and electric lighting.

Hotel del Coronado was built with grand dining rooms and large public spaces. When it opened it featured 399 rooms (now over 700). It was one of the first hotels in the world to have electric lighting, as well as one of the largest resorts in the world at the time. The hotel even supplied the entire city of Coronado with electricity.

For those who couldn’t afford such luxury, boarding houses and inns offered the basics: a bed, a meal, and little more. No marble, no chandeliers, just the essentials.

After World War II, travel changed dramatically. The rise of the American road trip created demand for something more consistent and affordable. A man named Kemmons Wilson, frustrated at paying $2 extra for each of his five children on a family trip, started what became the Holiday Inn brand. The first opened in Memphis, Tennessee on August 1, 1960. Holiday Inn was the first to let children stay for free, the first to guarantee a restaurant at every property, and by 1983, the first to offer a loyalty program. The modern hotel chain was born.

Today

Fast forward to today, and the hotel experience is, in many ways, very different. From 2016 until early 2020, I traveled around 45 weeks a year across the United States and Canada for work. During that stretch, I was unwaveringly loyal to Hilton. At the time, all of my research pointed to brand loyalty as the key to maximizing travel perks. I see things a little differently now, but more on that later.

Most of my stays were at Hampton Inns or Hilton Garden Inns. These hotels are usually clean and well maintained, though there are exceptions. What stood out to me over time is that nearly all hotels today, even luxury brands, treat the guest experience more like a transaction. Hospitality is still there, but genuine personalization has mostly disappeared.

Yes, Marriott, I notice when my name flashes on the TV as I walk into the room, but that’s just software tied to the reservation system, not real human connection. At least it confirms I’m in the right room. Compare that with the time I checked into a Hilton Garden Inn and found a bottle of wine waiting on the bed. That felt personal, thoughtful, and memorable. Those are the kinds of touches I miss.

Reviews

Which brings me to how I judge hotels today: reviews. Most of us, me included, check reviews before booking a stay (or even buying a universal remote for that matter). But how much weight should we really give them?

The answer is: they matter, but you have to read them critically. Suppose you find a hotel you like and see it has a 3.8/5 on Google. The instinct is to move on, but stop and dig deeper. I’ve stayed at some excellent 3.8-rated properties where the negative reviews had nothing to do with cleanliness or service.

For example, many low ratings say things like, “Very nice room, great staff, but too pricey at $300 a night.” That’s valid, but maybe you already found a rate for $198. Others complain, “Amazing staff, the room was bright and clean, but the elevator was too slow.” To me, that’s hardly a deal breaker.

When I scan reviews, I look for two words: “dirty” and “rude.” If those pop up repeatedly, I move on. The same applies to glowing reviews too, scan quickly and see if the praise lines up with what you are looking me.

And when it comes to leaving reviews yourself, remember they matter to the people behind the desk. I usually leave five stars, or nothing at all. If a property truly goes out of its way to make my experience poor, I’ll write a one-star review, but that’s rare. Be honest, but fair. Someone’s livelihood may be tied to what you write and others will make a decision based on what you write.

Loyalty

Does loyalty to a hotel brand matter? The short answer is yes, but there is more to it. First, what type of traveler are you? If you stay in hotels only five nights a year, then loyalty probably isn’t as important, unless those five nights are always at the same property.

There is a big difference between brand loyalty and property loyalty. Brand loyalty matters only for the perks spelled out in the program. For example, I’m now Titanium with Marriott because I’ve stayed more than 75 nights in a year (plus a few credit card bonus nights). That status rewards me with points, but more importantly, I’m allowed 4 PM check-out at most hotels. For me, that’s a game changer.

On the other hand, being loyal to the same property doesn’t matter much to Marriott as a brand, but it can matter to the hotel itself. If you’re a returning guest who has built rapport with the staff, you’re more likely to be upgraded or maybe given a little extra, like an additional bottle of water.

The most important thing to remember about brand loyalty is not to expect more than what’s written in the policy. I learned this the hard way during my 222 nights with Hilton. With that many nights, I could have had elite status with nearly every major hotel chain. I did earn a lot of Hilton points, which was nice, but I expected something more. I wasn’t sure exactly what, but I figured dedicating over 60% of a year to one brand would come with an extra gesture of appreciation. It didn’t, and I should have managed my expectations.

One moment stands out. Early the next year, I asked for my free bottle of water at a Hampton Inn. The woman at the desk looked up my account, confirmed I was Diamond, and then double-checked with her co-worker to make sure I hadn’t already been given one. I couldn’t help but think, “I spent 222 nights last year at an average of $150 a night, and I have to go through all this for a bottle of water?” The truth is, I didn’t spend 222 nights at that Hampton Inn. It’s independently owned, and as minor as a bottle of water seems, it still costs money. I didn’t earn the right to demand it there, or anywhere.

If you’re just starting out, do yourself a favor and spread your stays around. Remember, at the end of the day, to the brand you are a transaction. Find the properties you enjoy and that make sense for your travel. This should include some independent hotels too. Over time, you’ll naturally discover which brand you prefer, and when you search for hotels, you’ll start there.

Loyalty does matter, but it shouldn’t be the end-all, be-all.

Luxury Isn’t Always Luxurious

What is luxury, really—and do you need it?

Back at the start of this article, I mentioned wishing I could have stayed at The Waldorf in New York City during the late 1800s to experience that kind of luxury firsthand. I’m sure there are modern hotels that come close, but today it’s hard to tell with so many “false luxury brands” competing for attention. You might assume that simply following the money and booking the most expensive property will guarantee lavishness. In reality, you’ll be wrong more often than right.

This is one industry where higher price doesn’t always equal higher quality. I’ve seen a three-star hotel priced almost the same as a five-star. For example, I did a quick search for the end of October in Washington, D.C.: a Courtyard by Marriott was listed at $399 per night, while Le Méridien was $409. Le Méridien is a far nicer brand than Courtyard and well worth the extra $10 in my opinion. But then you see the St. Regis at $1,706 per night. It’s certainly considered an elite hotel, but I don’t see $1,000 worth of difference compared to Le Méridien.

So, do you actually need luxury? That depends on what you’re looking for on a particular trip. Most people’s idea of luxury often doesn’t match the experience—or the money spent.

A few weekends ago, I stayed with friends in Jacksonville Beach, Florida. We booked a SpringHill Suites right on the ocean. It’s one of Marriott’s mid-tier brands, about on par with a Hilton Garden Inn. It wasn’t luxury by definition, but it was oceanfront, had a bar and restaurant, was very clean, and delivered everything I needed for $250 a night.

On the other hand, I’ve redeemed points to stay at the St. Regis in New York City, where rates are often over $1,000 a night. That included a butler, turn-down service, and other extras. It was one of the rare hotels that actually lived up to the kind of luxury I imagined back in 1888. Still, had I paid $1,500 cash for the room, would I have felt I received seven times more value than at a Residence Inn a few blocks away? Personally, no.

Will I stay at high-end properties again? Absolutely, but only when it makes sense. Luxury is relative, just as loyalty and reviews are, it all depends on what you value most as a traveler.

Searching and Booking

You’re about to sit down and plan a weekend trip to Miami Beach, but where’s the best place to start looking? There are so many different third-party sites that can help, such as Hotels.com, Booking.com, and others. These sites do a great job of showing what’s available in the area, but please take my advice: do not use them to actually book your reservation. Booking direct will save you a big headache in the long run. (I even have an entire article on this topic if you’d like to dig deeper.)

That said, third-party sites are still useful for research. In addition, your credit card company likely has its own hotel booking tool, which can be another good resource. Just remember to use more than one option when comparing.

Personally, I like checking Marriott, Hilton, and IHG websites directly. Another underrated approach is to open your preferred map app, like Google Maps, zoom into your destination, and simply search for “Hotels.” You’d be surprised how many good options pop up that way.

Finally, even if you don’t travel for work, your company might work with a travel agent that allows personal bookings. It’s worth a quick look.

No matter how you search, the bottom line is this: explore your options anywhere you like but always book direct. Booking direct also ensures your loyalty nights and perks are recognized, which third-party sites often don’t honor.

Location, Location, Location

At the peak of my work travel, I often traveled with others on the road. They would usually book the hotel closest to the customer, but I always focused on where I’d be spending my time before and after work.

If you’re exploring a new area, keep these things in mind when selecting a hotel:

• How many restaurants are nearby?
• How far is public transit?
• Will I need a car if I choose Hotel A over Hotel B?
• Is the area walkable?

It doesn’t make sense to save $30 a night on a hotel only to spend $50 a night Ubering back and forth-or to end up relying on food delivery for every meal. Location is more than a convenience, it can actually save you money.

Summary

In the end, hotels are more than just a place to sleep, they’re a part of your travel experience. History shows us how far the industry has come (or hasn’t), but today it’s about understanding what really matters to you. Reviews can help, but only if you read them carefully. Loyalty can pay off, but it’s never guaranteed. Luxury can be wonderful, but it isn’t always worth the price tag. Planning and booking wisely, and choosing the right location, often make more of a difference than brand names or star ratings. At the end of the day, the “best” hotel is the one that fits your trip, your needs, and your expectations.

Hotel FAQ

Should I book direct or use a third-party site?

Use third-party sites for research, then book direct. Direct bookings are easier to modify or cancel, your loyalty nights and perks are recognized, and you avoid most “call the agent” runarounds.

Do hotel reviews really matter?

Yes, read them critically. Scan for repeat red flags like “dirty” or “rude.” A 3.8 score can still be fine if complaints are about price or a slow elevator, not cleanliness or service.

Does loyalty to a brand pay off if I only travel a few times a year?

Usually not. Loyalty is most valuable if you stay often enough to reach status where perks like 4 PM checkout matter. Otherwise, choose the best property for the trip.

What is the difference between brand loyalty and property loyalty?

Brand loyalty earns published perks, for example points and late checkout. Property loyalty is about rapport with a specific hotel, you may see thoughtful touches, upgrades, or small extras.

Is a higher price the same as higher quality?

No. Prices swing by date and demand. Mid-tier hotels can be priced near luxury properties. Compare brands, location, and recent reviews, not price alone.

How important is location when choosing a hotel?

Very important. A slightly cheaper hotel can cost more after rideshares and delivery fees. Check restaurants nearby, public transit distance, walkability, and whether you need a car.

When should I file a complaint about a hotel stay?

Report issues that affect safety, cleanliness, or sleep quality as soon as they occur, calmly and in detail. Ask for a remedy first, then escalate to a manager or customer care if needed.

How do I evaluate a hotel with a mixed rating?

Sort reviews by “most recent,” look for patterns over the last 90 days, and weigh comments about cleanliness and staff more than decor or elevator speed.

How can I get late checkout?

Status helps. If you do not have status, ask politely at check-in, offer a specific time, and note that you can skip housekeeping. Hotels are more flexible on off-peak days.

What is a smart way to search for hotels in a new city?

Use brand sites like Marriott, Hilton, and IHG, compare with your card portal, and scan Google Maps in the target neighborhood. Then book direct with the hotel.