How to Win Holiday Bookings • WebRezPro

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Both a joyful and stressful time, the holiday season brings a torrent of travelers into the market. As of 2023, 115.2 million people were predicted to travel at least fifty miles during the December 23rd–January 1st period. 

While this typically means an increase in bookings, the ever-expanding selection of options (from new hotel brands to Airbnb rentals) also means that competition is getting hotter. It’s time to gear up your marketing efforts to ensure your property gets its fair share of holiday bookings.

Running holiday specials and packages is a proven way to attract guests. When designing these, know your specific audience and what most appeals to them by using the data stored in your property management and customer relationship management systems. For instance, if many of your guests travel with pets, you could include a holiday treat for Fido as well. 

In addition to crafting the right offers, your guest data can also be used to create customer personas for ad campaigns and to decide what potential audiences to target. Pro tip: Retarget consumers who engage with your ads but who might not be ready to book yet…

Find out what your competitors offer and top it—not necessarily by providing a bigger discount but by putting a more creative spin on your promotions. Slashing prices can backfire, especially now when guests are primed to travel, and erode your credibility. Partnering with local businesses helps to expand both your offerings and your marketing opportunities by allowing you to access your partners’ audiences. At the very least, you can scoop up a joint social media post or backlink. 

Timing is critical as well. A correctly timed offer is an opportunity, while a poorly timed one is a nuisance. Look at when previous campaigns were opened. If a holiday campaign generated the most responses a few weeks after you sent it, delay the launch the next time around. Conversely, don’t leave it so late that guests have already made plans.

A modern property management system enables you to arrange all this with flexible rate management tools, robust data collection, and advanced booking capabilities. Guests should be able to book special packages directly from your online booking engine! 

Food matters at this time of year and at every other time. According to Hilton’s 2025 travel trends, nearly one of every five leisure travelers around the world plan to search for new culinary experiences. Guests book with their stomachs. 

Added to that, cooking for the holidays can be a hassle, so offer your guests those traditional holiday dishes without the dishes. No scrubbing plates, just sweet potatoes. 

Make sure all guests can partake by providing options for specialized diets, for example, gluten-free and vegan choices. Be careful of cross contamination as well. For some guests, those choices aren’t truly choices (the other choice is an evening on the toilet). 

For something extra special, arrange holiday events or activities on site. Think big, like Christmas markets, parties, or performances—or smaller, like cookie-decorating stations, card-making workshops, snowman-building competitions, or a toy drive. 

If you do something charitable like a toy drive, you could tie it to your loyalty program. A guest could receive a small amount of loyalty points (say enough for a free peppermint mocha) when they bring a toy in. This in turn could boost loyalty program memberships and keep those guests coming back.

Such activities can be marketed to the local community as well as prospective guests and contribute to a memorable holiday stay experience. 

A beautiful Christmas tree in a hotel lobby
Does it feel like Christmas at your property?

The holidays aren’t the same without glitter and sparkle, so make sure your property is dressed for the occasion with seasonal decorations—like a Christmas tree for the lobby, fairy lights for the patio, festive napkins for your breakfast bar… Don’t get too carried away though; there is such a thing as too much tinsel! 

Holiday-themed amenities go down a treat with guests too. How about a gift-wrapping or hot chocolate station in the lobby?

Guests are primed to expect your best offer on Black Friday, so take advantage of this. In recent years, the Black Friday period has even grown to include more than just the day, with Booking.com beginning their promotions around November 16th in 2024. This enables businesses to use deadlines to generate urgency while avoiding the consumer battle royale. Be sure that both your team and tech are in place; this is not a good time for a website crash. Your booking process for this and other offers should be simple and streamlined.  

Let guests know all the fun festivities you have planned by spreading holiday cheer to your website. Update property images and consider decorating with a tasteful touch of festive graphics and messages. Again, be careful not to go too far.

Holiday specials should be up to date and available through your booking engine, with clear deadlines to create urgency. Promote your holiday menu as well, and for properties that sell gift certificates, now’s the time to draw attention to them. Show these off right up to the last minute as they could be a lifesaver for whoever needs a gift asap. 

Add a holiday spin to your blog and local attractions page by highlighting seasonal activities and events, complete with insider tips like the best decorated street and best spot to watch the NYE fireworks. 

Be sure that your website is mobile friendly with a responsive design that adapts to the user’s screen. According to Adobe, 53 percent of online sales will happen via mobile in the upcoming 2024 holiday season. 

Drum up excitement and drive traffic to your website through your social media accounts. Post images and videos showing how your property is prepping, from putting up that magnificent tree to that drool-worthy dish your chef created. Boosting posts that perform well gains you even further reach.

You can also increase engagement with contests and polls. Offer followers the chance to win a free holiday package upgrade (for example) by liking, commenting on, or sharing your property’s post. Inspire user-generated content by creating and promoting a holiday hashtag that guests can use to post their own on-property pics for the chance to win. 

Put a booking link directly on your social media channels for browsers who are ready to become bookers. Facebook has a call-to-action button while Instagram now allows you to add multiple links to your bio. 

Email is still one of the best methods to communicate with customers. In addition to sending campaigns to segmented mailing lists, booking confirmation and pre-arrival templates can also be updated to include information about holiday upgrade offers and seasonal amenities. And why not send past guests a special discount or promo just for them? Exclusivity is always a draw. Property management systems that offer automatic emails (and/or CRM integrations) and the ability to create password-protected rates make these campaigns a breeze.

SMS is another great way to reach out directly as these messages have a 98 percent open rate. Keep them simple and consistent, with a clear call to action. WebRezPro integrates with several SMS providers, including Akia, Breezeway, and Duve.

Tap into holiday narratives and put your own special twist on them; this is where your unique selling proposition comes in. Parents don’t want to leave their children home alone? Mention your kids club. Single traveler tired of getting the couch when they visit family? You have a king bed. Don’t be afraid to mention stress points, especially if you have a sense of humor about them. Remember you’re the solution. What holiday emotions do you experience, both positive and negative, and how can you use them so that your guest empathizes?   

Remember that the story has changed since the 1950s (classic carols notwithstanding), and holiday families don’t look like how they were portrayed then. If you want diverse customers, you should have diverse promotional material. Also, dad might be the one cooking the turkey…

As with any marketing campaign, you need to know how well your holiday offers performed so that you can make appropriate adjustments and hand out any well-deserved kudos to your staff. Using WebRezPro’s market and source codes, you can track where your bookings originated and discover which channels were most effective (don’t rely on one channel, spread your marketing out!). Some of this analysis should even be conducted before holiday marketing begins so that you can select your ideal channel mix. 

Analysis also determines if you have the right price point. It’s best to use dynamic pricing (pricing that changes based on demand and other market factors). Look at past campaigns, booking history, and recommendations from your revenue management system. 

As temperatures drop and competition heats up, offer guests something special to stand out. You’re sure to win holiday bookings—and great reviews too.

Editor’s note: This post was last updated in November 2024.