21 Profitable Winter Side Jobs to Boost Your Income in 2023

As a small business consultant who has helped many entrepreneurs start seasonal side hustles, I know that winter brings ample opportunities for those looking to earn extra income. The holidays and colder weather create needs that savvy workers can capitalize on.

In this detailed guide, I‘ll share 21 of the most lucrative winter side jobs perfect for padding your wallet this season. I‘ll provide tips to get started, average earnings potential, and things to keep in mind for each idea.

Whether you want to spend time outdoors, put your skills to use, or spread some holiday cheer, you‘re sure to find a great seasonal job on this list!

Dog Walking

Brisk winter days are ideal for dog walking. Pet parents often prefer to stay cozy indoors and rely on dog walkers to keep their pups fit and happy.

Average Hourly Earnings: $15-$20 per 30 minute walk (Source)

Getting Started: Create a profile on sites like Rover or Wag to connect with pet owners in your area. Highlight your experience with dogs (if any), background screening, availability, and rates. Bundle up for the weather and be prepared with doggie cleanup bags!

Snow Removal

For those living in cold climates, snow removal can mean big business in the winter months. Homeowners and companies will pay for prompt, quality snow clearing services to maintain safe, accessible properties.

Average Hourly Earnings: $20-$50 per hour depending on equipment and size of property (Source)

Getting Started: Invest in key equipment like a snow blower, plow, snow shovel, and salt/de-icer. Market your services aggressively before the winter hits. Offer snow removal by the inch or by the job. Clear snow promptly after snowfalls for happy repeat clients.

Holiday Decorating

Too busy to deck the halls? Many people hire holiday decorating help starting in late November through December. Offer services like outdoor lighting, tree trimming, mantel and banister garlands, wreaths and more.

Average Hourly Earnings: $40-$70 per hour (Source)

Getting Started: Advertise your services early. Stock up on supplies like lights, ornaments, ribbons, garlands, etc. Consider offering add-ons like storage between seasons. Be sure you have the physical stamina for decorating, climbing ladders, etc.

Gift Wrapping

Gift wrapping is a huge time sink around the holidays. Stand out by offering quick, beautiful wrapping that will make gifts look top-notch under the tree.

Average Hourly Earnings: $10-$20 per hour base, plus tips (Source)

Getting Started: Set up a gift wrapping station in your home or offer mobile wrapping services at clients‘ homes. Stock up on quality wrapping papers, ribbons, gift bags, gift tags, tape, scissors and other supplies.

Personal Shopping

Take the stress out of holiday shopping by offering personal shopping services. Clients can provide gift lists and budgets, and you handle the rest!

Average Hourly Earnings: $25-$50 per hour (Source)

Getting Started: Get to know local stores, sales, and shops. Ask clients their desired stores, brands, price range and ages/interests of gift recipients. Provide receipts and handle returns as needed.

Event Staffing

Extra staff is crucial for corporate holiday parties, catered events, hotel parties and other events. Earn cash working as servers, coat check attendants, parking attendants, setup crew, etc.

Average Hourly Earnings: $12 – $18 per hour plus tips

Getting Started: Check job boards and contact local catering companies, event spaces, hotels and convention centers about seasonal work. Having a professional appearance and positive attitude go a long way.

Holiday Baked Goods

Capitalize on high demand for holiday treats like specialty cookies, pies, dessert breads, hot chocolate kits and more. Take custom orders or sell at holiday markets.

Average Hourly Earnings: $15-$35 per hour (Source)

Getting Started: Ensure you have the proper equipment and licenses/permits required for selling baked goods in your state. Develop recipes and calculate material costs. Take pre-orders and payments. Package baked goods beautifully for gifting.

Firewood Delivery

As temperatures drop and fireplaces get used, demand for firewood spikes. Offer split, seasoned firewood for delivery so homeowners can easily enjoy cozy nights by the fire.

Average Hourly Earnings: $200 – $550 per full cord delivered (Source)

Getting Started: Determine pricing based on your region and wood type. Split and properly cure/season wood 1-2 years prior to delivery. Own or rent a truck for deliveries. Accept online orders and promotions to boost winter sales.

Snow Shoveling

Shoveling snow is tough work but pays well for the service provided. Many homeowners, apartment complexes and businesses need pathways and sidewalks cleared after snowstorms.

Average Hourly Earnings: $20 – $35 per hour (Source)

Getting Started: Invest in a high-quality snow shovel. Reach out to homeowners and property managers in advance to offer snow removal services. Remain on-call to address new snow accumulation ASAP.

Handyman Services

Home improvement projects spike in winter since people spend more time indoors. Offer general handyman services for tasks like furniture assembly, hanging decor, appliance repairs, etc.

Average Hourly Earnings: $45 – $65 per hour (Source)

Getting Started: Highlight your skills and experience. Have the necessary tools and supplies handy. Offer fixed project pricing or hourly rates. Pay close attention to detail and provide quality customer service.

House Sitting

As homeowners travel for the holidays, demand for house sitters spikes to keep homes safe and cared for. Responsibilities generally include tasks like bringing in mail, watering plants and pet care.

Average Hourly Earnings: $15 – $25 per hour (Source)

Getting Started: Create a profile on house sitting sites like SitterCity or HouseSitter. Highlight any experience caring for homes or pets. Provide 2-3 verifiable references. Undergo background checks as needed. Review home care instructions closely.


Parents often seek academic support over winter break to reinforce skills or get ahead before the next semester. Offer tutoring in your areas of expertise!

Average Hourly Earnings: $15 – $40 per hour (Source)

Getting Started: Highlight your education, experience and subjects/ages you tutor. Have a designated tutoring space in your home. Use engaging games and activities in lessons. Offer online or in-person sessions based on comfort level.

Termite Inspections

Winter is prime time for thorough termite inspections since spots are more accessible when not obstructed by foliage. Home buyers especially want up-to-date termite clearance letters.

Average Cost Per Inspection: $75-$200 (Source)

Getting Started: Become certified in your state to perform wood destroying organism inspections. Invest in proper protective clothing and inspection tools. Market inspection services to real estate agents with pending sales. Provide detailed inspection reports.

These are just some of the most popular and profitable winter side jobs out there. With proper preparation and marketing, seasonal work can be both rewarding and lucrative. Don‘t let the winter slow your earning potential. Bundle up and make it your most profitable season yet!