How to Score Real Holiday Travel Deals

Black Friday and Cyber Monday have become major events in the travel industry, with airlines, hotels, and booking sites flooding your inbox with “incredible deals” and “limited-time offers.” Some of these are legitimate money-savers that can help you stretch your travel budget further. Many, however, are just clever marketing designed to make you think you’re getting a deal when you’re not. 

The key is knowing how to distinguish between them so that you can book with confidence instead of regret.

Think of it this way: travel companies know that the promise of a “deal” gets people to pull out their credit cards faster than almost anything else. They’re counting on you to book quickly without doing your homework—comparing prices, reading the fine print, or checking if those dates actually work for your plans.

But here’s the good news: once you know what real deals look like and which red flags to watch for, you can navigate these sales like a pro. Let’s save real money on trips you actually want to take, instead of getting lured into purchases that only seem like bargains.

Real Holiday Travel Deals vs. Marketing Tricks

Black Friday and Cyber Monday have become major events in the travel industry, with airlines, hotels, and booking sites flooding your inbox with “incredible deals” and “limited-time offers.” Some of these are legitimate money-savers. Many are just clever marketing designed to make you think you’re getting a deal when you’re not.

Here’s how to tell the difference.

What Real Holiday Travel Deals Actually Look Like

Percentage discounts on specific routes or properties: Airlines offer 20-30% off select routes for off-peak travel (like January-March). Hotels discount specific properties by 25-40%. These are real savings if you were already planning those trips.

Pro tip: If you’re planning a relatively expensive trip, you can consider signing up for one of the credit card companies’ loyalty programs, where you can get 80,000-100,000 bonus points upon signing up and reaching the minimum spend within the allotted timeline. These are genuinely valuable, but keep an eye on when the annual fee will arrive, and set a reminder to call one month before to cancel the card. Every time I do this, the customer service waives the annual fee – if you want to keep the card. 

Common Fake “Deals” That Aren’t Deals at All

• “Up to 50% off” (on dates nobody wants): The discount only applies to random Tuesdays in February to unpopular destinations. The flights you actually want? Full price.
• Hotel deals without mandatory fees: “$99/night!” doesn’t mention the $45 resort fee, $30 parking, and $25 early check-in. Your actual cost? $199/night.

In these cases: It’s essential to know what the baseline price would be and compare results across multiple sites. This way, you can tell if a ‘deal’ is really worth it. You can use Google Flights to see the typical pricing on flights, for example, if you haven’t been tracking the prices already.

Red Flags That Scream “Scam” (or Just Bad Deal)

Not all travel deals are created equal, and some are downright dangerous. Here are the warning signs that should make you pause—or run in the other direction.

Pressure Tactics and Fake Urgency

• “Only 2 seats left at this price!” or “Sale ends in 3 hours!” are classic pressure tactics designed to make you book before you have time to compare prices.
• How to spot it: If a site uses countdown timers or pop-ups screaming “BOOK NOW,” be skeptical.

Don’t buy these: Legitimate deals give you time to make an informed decision.

Pro tip: Open the same deal in an incognito browser window. That “only 2 seats left” message often shows different numbers or disappears entirely.

Prices That Are Too Good to Be True

Roundtrip flights to Europe for $200 or luxury resorts for $50/night? Your scam radar should be pinging. Mistake fares exist, but they are corrected within hours. If an impossibly cheap deal has been available for days, something’s wrong.

Red flags for sketchy booking sites:

• No physical address or customer service phone number
• Requests for payment via wire transfer or gift cards
• No secure payment (look for “https://” and a padlock icon)

Pro tip: Watch out for this new hotel reservation scam that’s been going around.

Blackout Dates and Impossible Restrictions

A deal advertises “50% off hotels” but every date you want is blacked out, or it only applies if you stay 7+ nights on weekdays during off-season.

Read the terms and conditions before you book. If the restrictions make it nearly impossible to actually use the deal, it’s bait, not a bargain.

The bottom line on red flags: Trust your instincts. If a deal feels rushed, too cheap, or comes from a site you’ve never heard of, slow down. Legitimate travel deals don’t require panic-booking.

Where to Find Legitimate Holiday Travel Deals

Now that you know what to avoid, here’s where to actually find real travel deals during Black Friday and Cyber Monday.

Airline Flash Sales and Mistake Fares

Airlines do run legitimate flash sales during the holidays, usually announced via email or social media. Sign up for email alerts from airlines you fly frequently—you’ll get notified when sales go live.

Best sources for mistake fares:

• Going (formerly Scott’s Cheap Flights) – sends alerts for error fares and deep discounts
• Secret Flying – finds mistake fares and unusually cheap routes
• Google Flights – set up price alerts for routes you’re interested in

Pro tip: Mistake fares get corrected quickly, sometimes within hours. If you see one, book immediately and ask questions later. Most airlines honor mistake fares, but not always.

Hotel Loyalty Program Promotions

Hotel chains often run their best promotions for loyalty members during Black Friday/Cyber Monday. Even free memberships get access to these deals.

Sign up for loyalty programs before the sales start:

• Marriott Bonvoy
• Hilton Honors
• IHG Rewards
• Hyatt World of Hyatt

These programs often offer bonus points (20-30% extra), discounted rates for members, or “book 2 nights, get 1 free” promotions during the holiday season.

Credit Card Travel Portals

If you have a travel rewards credit card, check the issuer’s travel portal during Black Friday for exclusive offers. Chase, Amex, Capital One, and Citi often offer bonus points or statement credits on travel bookings.

Example: Chase might offer 10x points on hotel bookings through their portal, or Amex might give $100 statement credit on flight purchases over $500.

Deal Aggregator Sites You Can Trust

These sites compile legitimate deals from multiple sources – check these on the weekend of Black Friday to Cyber Monday:

• The Points Guy – posts curated Black Friday travel deals with analysis
• Thrifty Traveler – premium service finds mistake fares and flash sales
• Costco Travel – if you’re a Costco member, they offer package deals with real value
• AAA Travel – members get access to exclusive rates and packages

The bottom line: Real deals come from recognizable sources—airlines, hotels, established booking sites, and trusted deal aggregators. Sign up for alerts ahead of time so you’re ready when legitimate sales drop.

Smart Strategies for Booking December Travel

You’ve spotted a legitimate deal—now what? Here’s how to book December holiday travel strategically.

Best Time to Book Christmas and New Year’s Trips

• For domestic flights: Book 1-3 months before departure. For Christmas travel (Dec 20-26), late September through November is the sweet spot.
• For international flights: These should be booked 2-4 months out, so it’s likely too late now, but you can watch for airline deals for early 2026 trips.
• Black Friday/Cyber Monday timing: If you haven’t booked December travel yet, late November is actually ideal. You’re in the window where deals appear, but panic pricing hasn’t hit.

Use Flexible Date Searching

• Google Flights calendar view: Shows prices across an entire month. Flying one day earlier or later can save $150+ per person.
• Avoid peak days: December 23, 24, and 26 are most expensive for Christmas. December 20-22 and 27-28 are cheaper.

Pro tip: Red-eye flights and early morning departures (before 7 AM) are often cheaper and less crowded.

When to Book Now vs. Wait

Book now if you can find a deal that has any or some of these features:

• The price is 15-20% below average (check Google Flights’ price history)
• Your dates are inflexible
• You’re booking a popular route that sells out
• The deal includes free cancellation

Wait if:

• Prices are higher than average
• You have flexible dates
• You’re waiting for Black Friday/Cyber Monday deals

When you’ve got your trip booked head on over to covertrip.com to insure it – you can’t predict the weather, after all!