4 Seasonal Side Gigs To Pay Off Holiday Expenses
Written by
Andrew Lisa
Edited by
Rebekah Evans
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The winter holidays are in the rearview mirror, but the credit card statements that made them possible are starting to trickle in — and Santa wants his due. The National Retail Federation estimates the average American’s winter holiday tab is creeping toward $1,000, breaking the $900 mark for the first time in history in 2024 — and that’s just for merchandise and doesn’t include budget busters like travel.
If you’ve got some financial catching up to do, you might be looking for a side hustle to get you back above water so you don’t enter spring in destitution. The time for many of the often-cited seasonal gigs — Christmas tree lot attendant, retail cashier, Amazon warehouse worker, etcetera — has passed and many of those require hard work for low pay and little fulfillment, anyway.
The good news is that they’re hardly the only gigs in town. The following seasonal side hustles are accessible to the masses, pay well and can become year-round gigs or even full-time work should you try one and like it.
Tutoring
Winter is the runup to the busy college application season or, for younger students, the SATs and other standardized tests. Colleges change semesters as spring approaches, which means students will be evaluating what they did right and wrong in the classes they’re exiting so they can improve in those they’ll enter in the spring.
According to a recent article from Crafting Scholars President and CEO Kris Harris, those are just some of the reasons why students and their parents flock to tutors in the winter — and bring their wallets with them.
Salary.com lists the median earnings of a tutor in the U.S. as $29 an hour.
Virtual Assistant
According to Virtual Assistant Statistics 2025: Insights and Trends from There is Talent, the virtual assistant (VA) field is one of the fastest-growing and in-demand services, boasting a projected compound annual growth rate of over 20% through 2027.
Much of that soaring demand comes in the winter when side hustlers can get in on the action to dig themselves out of their holiday holes. The report sheds light on why.Â
The three industries driving most of the growth are healthcare, which sees rising demand in the winter, real estate, which spends the cold months preparing for the frantic spring busy season and e-commerce, which booms in the winter because millions of people just like you make it a habit of overspending during the holidays.
VAs are self-employed, work from home and typically have flexibility as to when they provide administrative, technical and creative support to their remote clients. If you have strong organizational, computer and communication skills, the barriers to entry are relatively low and Indeed.com cites the average pay at more than $27 an hour.
Pet Sitter or House Sitter
According to the 2024 TripAdvisor Winter Travel Index, winter is one of the year’s busiest travel seasons — and it has broken the chains of the traditional Thanksgiving to New Year’s mold to include the entirety of the cold months.
When people travel, they leave their houses and, in most cases, their pets behind — both need extra TLC in the winter — creating increased demand for caretakers. Care.com cites the average pay for house sitters at $19.29 per hour, with many earning about $50 to $100 per day. Indeed.com reports that pet sitters earn an average of $16.27 an hour.
Resort Worker
The winter travel surge that TripAdvisor chronicled creates seasonal demand not just for the houses and pets that travelers leave behind but also for the resorts they flock to when the cold sets in — and you don’t have to live near Playa del Carmen or Cancun to get in on the action.
From the Poconos in the East to Lake Tahoe in the West, most regions in America have access to resorts large and small that bloom in their busy seasons, giving everyone from bartenders and housekeepers to lot attendants and managers the chance to earn some extra cash. The pay varies widely depending on your location and vocation. However, it’s a something-for-everyone industry, with Indeed.com reporting wages ranging from barely above minimum wage for brand ambassadors to about $40 an hour for accountants.
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