As temperatures dip, many small business owners start battening down the hatches in anticipation of slow winter months. However, with the right mindset shift, you can discover surprising opportunities during the off-season to not only sustain, but grow your income.
From time-tested winter classics to innovative pop-up ideas, this guide covers 25 businesses perfect for converting winter downtime into profits. I‘ll provide insider tips to get each venture rolling along with projections to quantify earning potential.
By trying one or more of these creative concepts this winter, you can bolster your bottom line while having fun and flexing your entrepreneurial skills.
Tradition Gigs That Deliver Cold Weather Cash
Certain services remain tried and true seasonal moneymakers, delivering stable returns year-after-year.
1. Clear the Snow – $30 to $50 per hour
As winter weather hits, clearing snow becomes less of an option and more of an immediate need for both residential and commercial clients. Investing in quality gear like a snowblower and pickup truck rack allows you to service multiple properties efficiently. You can expect to charge around:
- $30 to $50 per hour for residential driveways and walkways
- $100 or more for commercial parking lot plowing
Completing just five driveway jobs per 6-8 inch snowfall at $40 per drive tallies $200, showcasing profit potential.
2. Decorate for the Season – $200 to $7,500 per client Property size and extravagance of décor determines rates, which often start around:
- $200 for basic holiday wreaths and welcome signs
- $1,500+ for single family light displays and trees
- $7,500+ for over-the-top commercial installations
With practice, a two person team can complete multiple simple residential jobs per day during peak decorating season. Clear $1k+ weekly through Christmas as requests roll in.
3. Address Academic Needs – $20 to $50 per hour
Tutoring pay aligns with student age, subject matter, and session format, which includes:
- $20 to $30 for elementary school homework assistance
- $30 to $50 for high school exam preparation
- $30+ for specialized college test prep classes
Tutoring 5 students per week at an average of $35 per hour already generates $700 WITHOUT holiday session upticks factored in.
4. Craft Artisanal Goods – $25 to $250+ per item
Handmaking specialty winter accessories allows you to multiply profit margins rather than competing solely on price point. Unique options like felted wool mittens, soy candles, knitted ear warmers can retail from $25 to $250+ depending on materials, sizing, and personalization.
While time intensive, selling 30 mixed items monthly at an average of $125 each yields almost $4,000.
Innovative Winter Pop-Ups For Entrepreneurial Spirit
Looking to try a new income concept this winter? Pop-up trends take event, retail and experience-based concepts and distill them into temporary opportunities with lower risk and barriers to entry.
5. Capture Festive Portraits – $50 to $250 per session
Photographing everything from holiday card shoots to maternity sessions helps families freeze fleeting memories. Offer mini packages starting around $50 for 15-20 digital keepsakes along with premium sessions from $100 to $250+ for multiple people, outfits, and backdrops.
Charging $150 per shoot for 15 clients monthly already delivers $2,250 without intensive gear or studio space overhead.
6. Provide Holiday Pet Care – $20 to $50 per visit/walk
As families travel over winter holidays, pet sitting and dog walking requests surge. Charge rates like:
- $20 to $35 per 30-minute visit covering feeds, treats, and cuddles
- $20 to $50+ per 60-minute dog walk depending on number of pups
Just 2 scheduled walks plus 5 visits daily at an average of $35 tallies $245, multiplying rapidly across busy holiday weeks.
7. Sell Specialty Baked Goods – $2 to $50+ per treat
Capitalizing on demand for decadent flavors and giftable sweets, boutique holiday confections retail from $2 for cookies up to $50+ for artisanal cakes, generating sizable profits.
Wholesaling 100 custom cookies weekly at $5 each equates to $500 and facilitates larger orders from coffee shops, holiday markets and corporate gifting compared to individual sales.
8. Host Pop-Up Workshops – $25 to $200 per ticket
Leveraging specialty skills like crafting or mixology, pop-up classes allow you to share hobbies while earning income. Charge per participant, with rates spanning:
- $25 for quick kids craft workshops
- $50+ for weekend seasonal cooking classes
- $100 to $200 for intensive skills sessions like wreath making, flower arranging, or cocktail mixing.
With preparation, materials cost and ticket rate factored, hosting weekly kids crafting pop-ups with just 10 registrants at $30 each tallies $1,200 per month.
9. Rent Winter Gear – $25 to $75 daily
Help outdoor enthusiasts conveniently access pricey seasonal gear without long-term ownership commitment or costs. Potential rental rates include:
- Snow shoes – $25 to $40 per day
- Skis – $40 to $60 per day
- Snowboards – $50 to $75 per day
- Ice skates – $10 to $15 per day
Carrying just 20 sets of skis rented twice weekly at $50 daily = $2,000 in weekly income potential through winter.
10. Plan Memorable Winter Events – Starts at $75 per hour
Provide stressed hosts seamless corporate, family or community winter celebrations through specialty planner packages. Offer limited a la carte options starting around $75 per hour for planning meetings along with day-of coordination or fully managed events starting at $1,000+.
At an average rate of $100 per active planning hour, dedicating just 15 hours weekly = $1,500, allowing you to focus on prestigious clients over piecemeal rentals and decor.
11. Sell Cozy Clothing Creations – $5 to $250 per garment Marking up purchased inventory 4x wholesale cost and higher for handmade fashion allows substantial profit margins. Chunky knit sweaters could retail for $100 at $25 cost while temperature regulating base layers and coats sell from $175 to $250+ as performance pieces.
Pricing 30 curated styles at approximately $125 retail while wholesaling at $35 generates $1,125 weekly profit.
12. Book Winter Getaways – $50 to $150+ per booking
Help travelers book their dream ski, winter wonderland or holiday market escape while earning commissions from supply partners like resorts, tour operators and transportation. Set service fees according to trip complexity, starting around:
- Domestic weekend city stay – $50
- International multi-stop – $150+
Facilitating 5 domestic trips weekly at $75 per booking + estimated 8% supplier commissions tallies $525, amplified further by higher value and volume international bookings.
13. Sell Handcrafted Gifts – $5 to $75 per gift
Offering custom keepsakes with that homemade touch keeps winter retail interesting while allowing crafters to directly profit from hobbyist skills versus outsourcing manufacturing. Lucrative seasonal ideas include:
- Personalized ornaments and stockings – $5 to $25
- Holiday centerpieces – $25 to $50
- Artisanal advent calendars – $50+
Wholesaling 30 mixed creations weekly to local gift shops, winter markets, and galleries at an average of $35 each returns $1,050.
14. Maintain Winter Gardens – $35 to $65 per hour
While less intensive than warmer seasons, winter gardens still require attention. Offer seasonal pruning, protective mulching, plant health checks and more. Charge rates spanning:
- $35 per hour for regular garden cleanup
- $55 per hour for specialized winter landscaping projects
Servicing 5 residential clients weekly at approximately 3 hours each provides $55 per week totaling $2,750 per month.
15. Serve Up Warm Beverages – $2 to $5 per drink
Warming passersby while earning income, festive winter beverage stands offer steamy made-to-order drinks like hot chocolate, apple cider and wassail. Mark up ingredients 4x to 6x to retail around:
- Hot Chocolate – $3 to $4
- Specialty Cider – $4 to $5
- Adult Spiked Ciders – $7 to $9
Prepare inventory for 200 cups daily at approximately $4 each to profit $800 across a five day market, translating into $4,000 over four prime weekends.
16. Instruct a Winter Sport – $45 to $115 per lesson
Skiing, snowboarding, skating and sledding continue gaining popularity for kids and adult beginners, making instruction extremely profitable. Lesson rates range from:
- Group lessons – $45 to $65 per person
- Private lessons – $65 to $115 per person
Running after school group lessons with 6 kids at $55 each for 60 minutes delivers $55 per hour. Five days a week class revenue = $1,375 weekly, expediting instructor payback on gear and credentials.
17. Address Fireplace Issues – $50 to $150 per hour
Performing fireplace inspection, cleaning, installations and repair provides homeowners essential peace of mind while generating lucrative service income. Bill clients:
- Basic inspection and maintenance – $50 to $75 per hour
- Major repair projects – $100 to $150 per hour
Completing 2 large repairs weekly starting at $125 per hour + 5 maintenance calls at $65 per visit returns $2,700, factoring some overlap between shorter visits.
18. Ready Vehicles for Winter – $50 to $250 per service
Prep cars for icy conditions through offerings like snow tire installation, battery testing, heating checks and more. Service package rates span:
- Wiper and fluid refresh – $50
- Headlight restoration – $100
- Complete winterization package – $250
At roughly one hour per service, completing package upgrades on 10 vehicles weekly provides $2,500, amplified by à la carte requests.
- Kids craft workshops – $25 per participant
- Weekend adult group classes – $50 to $150 per seat
- Multi-week skill-building courses – $150 to $200 per seat
Charging $100 per 8 person class, hosting 3 full workshops weekly totals $2,400 while establishing expertise as demand expands in years to come.
20. Design Festive Events – $2,000 to $10,000+ per event
Elevate seasonal celebrations through complete planning and elegant touches showcasing your creativity. Service event types like:
- Intimate gatherings – $2,000+
- Corporate parties – $5,000+
- Nonprofit fundraiser galas – $10,000+
Working with just 1 substantial event weekly, contracted at approximately $5,000 each, provides $20,000 monthly during busy winter months.
21. Prepare Properties for Winter – $100 to $300 per project
Complete weatherproofing and maintenance allowing homeowners efficiency and cost savings once cold arrives. Offer:
- Caulking and insulation inspection – $100 to $150
- Pipe insulation and gutter protection installation – $150 to $250
- Complete weatherization package – $250 to $300
With materials included, 5 caulking jobs weekly at roughly $125 each returns $625, enhanced through enrollments in full-service winterization plans.
22. Provide Post-Holiday Cleaning – $30 to $60 per hour
Erase holiday clutter and refresh living spaces with deep cleaning services specializing in areas like floor care, window/surface scrubbing, storage solutions and more. Charge by project with rates spanning:
- General tidying – $30 per hour
- Deep cleaning packages – $50+ per hour
At only 15 billable hours weekly, providing lighttidying and decluttering at a modest rate of $35 per hour totals $525, allowing time for deep cleaning projects.
23. Offer Winter Storage Solutions – $50 to $500+ monthly
Monetize extra space by offering enclosed, 24/7 monitored storage units. Based on size and features, benchmark rental rates fall around:
- 5’x5’ locking unit – $50 per month
- 10’x 20’ temperature controlled unit – $275 per month
- Vehicle storage – $100+ per month
Filling a 20 unit self-storage facility churns approximately $5,000 monthly based on a moderate 50% occupancy blending various unit sizes and features.
24. Lead Winter Wellness Classes – $10 to $50 per class
Ward off seasonal sadness through workshops focused on activities like mindfulness, fitness, nutrition and creativity. Format sessions to align with venue size and duration, charging accordingly. Benchmarks include:
- Weekly lunch hour office classes – $10 to $15 per person
- 60-minute studio workshops – $20 to $25 per person
- Half and full-day retreats – $50+ per attendee
With minimal overhead beyond expertise, hosting just 2 weekly studio workshops with 10 participants at $20 each provides $400 of easy recurring income all winter.
25. Sell Seasonal Produce – $2 to $10+ per item
Despite cold, winter produce still flourishes thanks to cold-hardy vegetable varieties along with artisanal preserves, heirloom apples and more. Set booth rental fees according to market scale, then price items based on fair value spanning:
- Hearty greens – $3 to $6 per bundle
- Squash varieties – $2 to $5 per lb
- Specialty goods – $8 to $15 per jar or bundle
Vending at a single weekly market with approx. 100 daily patrons while averaging $20 total sales per customer equates to $2,000 income potential across core winter market season.
Key Takeaways
- Winter downtime disguises profitable possibilities for businesses adept at filling seasonal needs from holiday décor to events and cold weather prep.
- Temporary winter pop-ups allow first-time entrepreneurs to test ideas before committing long-term.
- While certain opportunities peak from November to February, research ways to adapt your concept into a year-round venture.
- Align operational scale with realistic income goals and availability, then reinvest profits into growing subsequent seasons.
Now It‘s Your Turn
Rather than dreading cooler months, view winter as a chance to try a new income stream while giving your core business sustained attention.
Start by identifying needs in your community, then determine how to address them based on your skills and interests. Establish a basic budget, gear checklist, and projected pricing to confirm profit potential.
The beauty of winter pop-ups is trying without extensive risk. So be bold, start small, and have fun with it! No matter what, you‘ll end the season having grown new capabilities to apply going forward.
Here‘s to a profitable new year! Let me know if you have any other questions.
