Our 8 Best Hotel Booking Tips: A Frequent Traveler’s Guide

We book a lot of hotels every year from weekend breaks to long-haul getaways, and from independent boutiques to big-brand resorts. After hundreds of nights on the road, we’ve learned which hotel strategies actually make a difference when booking and during the stay.

These practical hotel tips help us find better rooms, avoid inflated rates, and add comfort for a smoother travel experience. Plus one important safety tip that’s often overlooked.


1. Book Early and Keep an Eye on Prices

Nonrefundable bookings are tempting to save a few bucks in the short term, but we always book flexible rates when we can and it winds up saving us money in the long run.

Hotel prices and point redemptions tend to go up, especially in popular destinations, but prices do fluctuation over time. Booking flex rates early gives you access to potentially better rates and rooms but also the ability to recoup your investment if prices go down or plans change. And if you’re using points, you can lock in award pricing before a devaluation hits.

We set up a calendar reminder to check back every couple of weeks. Prices do periodically dip, and even can drop significantly closer to the check in date. If the price drops, we cancel and rebook. It’s the same hotel and same room, but for less money.

This works with cash and points bookings, as long as the rate is refundable. And if you’re choosing between locations or travel dates, don’t be afraid to book more than one option while you decide – as long as you cancel the extras on time. We did this for Greece in peak summer. We wound up switching our trip to Spain, but we locked in significantly lower rates by booking early, as well as flexibility to change our minds.

Hilton devalued points twice between booking and our stay

2. Book Direct with Major Hotel Brands for Perks and Protection

If you’re staying at a big brand, like Marriott, Hyatt, Hilton, or IHG, always book direct unless there’s a compelling reason not to. Also make sure you research which brand your hotel is a part of, if any. For example, I was surprised during a business trip to learn that the Hotel del Coronado was a Hilton property that honored my $200 AmEx Aspire resort credit and Diamond status upgrade. If you generally book through third-party sites (like Booking.com or Hotels.com) you might miss out on key perks.

Booking through the hotel’s own site usually means:

  • You’ll earn points and elite night credits
  • You’ll qualify for upgrades, breakfast, and other elite perks
  • You’ll have better customer support if anything goes wrong

We’ve had more than one situation where elite benefits weren’t recognized on third-party bookings, or the hotel wouldn’t even assign points. Booking direct also makes it easier to request room changes, resolve billing issues, or check in early.

Elite status can get you executive lounge access with free food and drinks


3. Know When to Book Through a Third Party

All that being said, we still use Booking.com, especially for independent or boutique hotels where the direct booking terms are strict or vague. We love to book direct with small or independent hotels so they don’t get hit with a big fee from booking platforms, but unfortunately, we’ve run into issues that make it way better for us to book third party.

Why? Because third-party sites often offer:

  • Better cancellation flexibility
  • Delayed or no up-front payment
  • Easier changes or cancellations through the platform
  • Safety guidelines and support if something goes wrong during your stay

But you still need to read the fine print. Look for:

  • When your card will be charged
  • Whether there are extra fees to be paid directly
  • How you’re supposed to cancel (online or by contacting the hotel)
  • What refund method is offered: card refund, site credit, etc.

You should also be sure to use a card with no foreign transaction fees. We got hit with a 3% charge once when our Booking.com transaction actually occurred in Europe, even though we booked at home in the US.

Sometimes booking a boutique is hard to do direct


4. Watch for Hidden Fees

A great hotel rate might not be so great once you add resort fees, service charges, and taxes. These aren’t always shown clearly upfront. The price can jump hundreds of dollars when you’re initially seeing the base rate for a nonrefundable twin room, and you’re booking a refundable king with a view. Then it jumps even more when taxes and fees are added at checkout, and then you also have a city tax and resort fee to pay locally on arrival. It’s sneaky and frustrating, but it happens all the time.

Before you commit:

  • Click through to the final booking screen to see the real total
  • Look for parking fees, “urban destination” fees, or housekeeping charges
  • Check whether breakfast or Wi-Fi is included or an add-on
  • Is breakfast included? If it’s an add-on, we usually pass and opt for something cheaper, better, and local.

While a hotel’s site can be more transparent than third-party platforms when it comes to all-in pricing, we find issues with both. Always check. And if you’re driving, parking availability and prices can vary significantly and make a huge difference.

Many resorts charge an extra fee to cover the pool and other amenities


5. Always Check the Real Photos

I’ve been a TripAdvisor member for 20 years, it’s not the trusted travel review site it used to be. But we still use it for the traveler photos and general reviews. The official photos on booking sites are always the best room on the best day with heavy filtering. Real photos tell you the true story.

We look at:

  • Bathroom quality and layout
  • How worn the rooms actually are
  • Whether there’s a view or you’re staring at an alley wall
  • Cleanliness, overcrowded areas (like lobbies, pools and beaches), and overall vibe

Even if you take the reviews with a grain of salt, we pick up some good info from the tips, and the traveler-submitted photos are usually still honest.

Do your Instagram vs. Reality homework before you book


6. Don’t Skip the Front Desk

We almost always check in in person. Even with mobile check-in available, we prefer to talk to a human, especially when:

  • We’re arriving early and hoping to get into a room ahead of time (we’re not going to get upset if a room isn’t available before check-in time, but it’s nice when it works out)
  • We’re asking about upgrades, better floors or views, or late checkout (even with hotel elite status we still have to ask the front desk to get these perks sometimes)
  • We want info about the neighborhood, amenities, or property layout (you can pick up some great information at the front desk to make your trip smoother)

We’ve also seen how mobile check-in can backfire. Once you’re assigned a room through the app, it’s harder to switch, especially if you’ve already triggered keyless entry. If there’s a better room available now (and yours isn’t ready yet), it’s a little more complicated. We still use the digital key, but we check in at the front desk first.

When is digital check-in the better option? If we’re not worried about the room assignment, we’re landing at midnight and just want to crash, or there’s a really long line, we’ll skip the front desk and head straight to the room.

We got this stunning room upgrade just by asking at check in


7. Don’t Be Afraid to Ask for an Upgrade

Even if you have status, upgrades aren’t always automatic. And if you don’t, you can still politely ask. You may be offered a nicer room or an upgrade for a surprisingly small fee. We’ve been offered:

  • Nicer views
  • Corner rooms
  • Premium suites with status or for a fee

Timing matters. If you’re checking in late-afternoon or at night, the hotel has a better sense of inventory for the night. Peak travel days and seasons, of course, have less availability. But if they have availability, it often costs them nothing to make your stay better. Make sure you’re polite, flexible, and not giving entitled vibes. If you’re going to be super disappointed by not getting the better room, be sure to book it outright rather than bank on an upgrade.

Just be careful: our beautiful suite upgrade came with construction work all day. No wonder the room was available


8. Always Get Your Final Bill and Fully Check Out

Even if you didn’t charge anything to your room, always request a printed or emailed bill at checkout.

We’ve had these small but annoying issues:

  • Charges accidentally added to our folio
  • Elite perks (like food and beverage credits) not applied
  • Minibar auto charges when we moved an item but didn’t consume it

More seriously, we’ve heard stories of rooms being “extended” by scammers after the original guest left, racking up huge charges under their name. If you didn’t formally check out, it’s harder to prove your stay ended when you say it did.

Always do the following:

  • Check your bill before you leave
  • Close the door behind you and make sure it locks (though some doors automatically unlock at checkout time now)
  • Follow up if anything looks off

It’s much easier to resolve issues at the front desk before you leave than to try and call later.


We still enjoyed the balcony for a bit

What are your tried-and-true hotel tips? Let us know in the comments.

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