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Winter Break Jobs in Wisconsin (NOW HIRING)

The Ingleside Hotel

Lifeguard - Water Park

Pewaukee, WI · On-site

$1.0K/day

We are open Thur-Sun during the school year; daily during spring break, summer and winter break. Great for those in online/home school or adults with teaching/medical experience. PT hours are ...

Reach DANE

Site Director

Madison, WI · On-site

$32/hr

Part Year includes built-in summer break, 2 weeks winter break, and spring break WHAT WE OFFER Comprehensive Benefits * Health, Dental, and Vision Insurance * Generous Paid Time Off & Holidays ...

Reach Dane

Site Director

Madison, WI · On-site

$32/hr

Part Year includes built-in summer break, 2 weeks winter break, and spring break WHAT WE OFFER Comprehensive Benefits * Health, Dental, and Vision Insurance * Generous Paid Time Off & Holidays ...

Reach Dane

Therapeutic Education Leader

Stoughton, WI · On-site

$36.50/hr

Part Year includes built-in summer break, 2 weeks winter break, and spring break WHAT WE OFFER Comprehensive Benefits * Health, Dental, and Vision Insurance * Generous Paid Time Off & Holidays ...

Reach DANE

Site Director

Madison, WI

$32/hr

Part Year includes built-in summer break, 2 weeks winter break, and spring break WHAT WE OFFER Comprehensive Benefits * Health, Dental, and Vision Insurance * Generous Paid Time Off & Holidays ...

Wisconsin

CASE- Trips Coordinator

Stevens Point, WI · On-site

$12.50/hr

Organize, promote, plan, and implement Alternative Winter Break Trip (e.g. Further Along) * Facilitate multiple pre-trip meetings for each trip destination * Attend and lead both alternative break ...

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All JobsWinter Break JobsWinter Break Jobs in Wisconsin

Winter Break information

What is the difference between Winter Break vs Summer Camp Counselor?

AspectWinter BreakSummer Camp Counselor
Required CredentialsNone or minimal; background checks often requiredCPR/First Aid certification; background checks; experience with children
Work EnvironmentSchools, community centers, holiday programsSummer camps, outdoor or recreational settings
Employer & IndustryEducational institutions, community organizationsRecreational and youth development organizations
Common Search & ComparisonHoliday seasonal work, short-term youth programsSummer employment, youth activity leadership

Winter Break roles typically involve short-term work during school holidays, focusing on holiday programs or community activities. Summer Camp Counselors work during the summer months, leading youth activities in outdoor or recreational settings. While both roles involve working with children, Winter Break positions are often more flexible and less specialized, whereas Summer Camp Counselors usually require specific certifications and experience in youth supervision.

What types of seasonal positions are commonly available during the winter break period, and how can I prepare for them?

During the winter break, many employers in retail, hospitality, and event management hire temporary staff to accommodate increased holiday demand. Common roles include sales associates, customer service representatives, food service workers, and event staff. To prepare, tailor your resume to highlight customer service or teamwork experience, and be ready for fast-paced work environments with flexible hours. Applying early and demonstrating a willingness to work during peak times, such as weekends and holidays, can improve your chances of being hired.

What is a winter break job?

A winter break job is a temporary employment opportunity that students or individuals take during the winter holiday period, typically spanning several weeks between academic semesters. These jobs can range from retail and hospitality positions to internships or administrative roles, providing a chance to earn extra income, gain work experience, or explore potential career interests. Winter break jobs are popular among high school and college students looking to make productive use of their time off from school.

What are the most commonly searched types of Winter Break jobs in Wisconsin?

The most popular types of Winter Break jobs in Wisconsin are:

What cities in Wisconsin are hiring for Winter Break jobs?

Cities in Wisconsin with the most Winter Break job openings:

Winter Break jobs near you
Infographic showing various Winter Break job openings in Wisconsin as of August 2026, with employment types broken down into 1% As Needed, 33% Full Time, 62% Part Time, and 4% Contract. Highlights an 99% Physical, and 1% Remote job distribution.

Winter Break Nanny

University of Wisconsin Madison

Fort Atkinson, WI • On-site

$18 - $25/hr

Full-time

Posted 6 days ago

University Of Wisconsin-Madison rating

8.3

Company rating: 8.3 out of 10

Based on 56 frontline employees who took The Breakroom Quiz

126th of 618 rated colleges and universities

Job description

Winter Break Nanny
Job No: 29556
Division/Organization: Abbe Family
Job Type: Local Student Jobs
Remote Eligbility: Not Remote
Location: Private Residence Fort Atkinson, WI 53538 (not on bus line)
Salary/Wage Range or Lump Sum: $18.00 to $25.00
Job Categories: Child Development and Care
Anticipated Hours Per Week
24-32
Schedule:
Opportunity to create a flexible schedule with more or less hours, depending on earnings ambition.
3-4 days/week
7:30-3:30pm (half days optional)
Mid-December through Mid-February (desirable)
Salary/Wage Range:
Hourly $18.00 to $25.00
Number Of Positions
1
Position Summary/Job Duties:
We are looking for a nanny over winter break for three sweet boys 3-4 days/week, from 7:30am - 3:30pm in Fort Atkinson, WI. Our full time nanny is expecting a baby mid-December and we are looking for someone to fill in while she takes her much needed maternity leave. Jimmy (4), Bobby (3) and Jack (2) are happy, healthy, full of energy and love to play rambunctiously with each other. Jimmy (4) and Bobby (3) will be attending 4K and 3K, respectively, in the mornings Monday-Thursday (8am-11am). Jack (2) will need a buddy to play with while the two older boys are at school. We are hoping the nanny we hire will be able to pick up the boys from school at 11am, which is about a 5 minute drive from our house. We handle dropoff in the morning and will provide the vehicle with the necessary carseats for pickup.
Daily duties include playing, feeding breakfast, lunch and snacks for the boys, changing diapers (Jack) or clothes, some light housekeeping such as tidying the kitchen and play areas, and putting Bobby and Jack down for a midday nap. We live in Fort Atkinson on a large lot which affords a lot of space for outdoor play. All three boys love anything and everything tractors, constrcution trucks, puzzles, singing and dancing, and just running around with inflatable balls in our large upstairs and finished basement play areas. We have tons of toys, games, and activities to keep the boys busy and burn off energy even when stuck inside during the winter months. We also love baking, art projects and reading books.
Ideally, we hope to hire someone who would be available mid-December through mid-February, but are willing to work with candidates given the academic schedule. We will be out of town for Christmas and whomever we hire will have off December 23-27 and December 31-January 1st. Days off around the holidays (in between Christmas and New Years) is negotiable - we just need to know your travel plans so that we may make a plan with our work schedules in advance! Half-days may be an option as well. Pay is $18-25 per hour based on prior experience.
Qualifications:
Prior experience with toddlers
CPR and First Aid Certified
Clean driving record (as applicable)
Physical Demands
Must be able to lift 50 pounds
Application Instructions:
Please email your resume to Kate at leverichk@gmail.com
Contact:
Org: Abbe Family
Contact: Kate Abbe
Email: leverichk@gmail.com
Advertised: August 10, 2026 05:00 AM CST Central Standard Time
Applications close: September 10, 2026 05:00 AM CST Central Standard Time
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What University Of Wisconsin-Madison employees say

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About University of Wisconsin

Sourced by ZipRecruiter

The University of Wisconsin, based in Madison, WI, US, functions in the educational industry and is a renowned and respected institution for higher education. Its official website is wisc.edu. Established in 1848, this public research university is recognized globally for its innovative approach to education, research, creativity, and public service. It embodies a strong commitment to academic freedom and academic excellence. As a major contributor to the Wisconsin Idea, it aims to accomplish its mission of generating well-rounded individuals who will contribute substantially to society, the local community, and the global economy.

Industry

Colleges, universities, and professional schools

Company size

10,000+ Employees

Headquarters location

Madison, WI, US

Year founded

2005

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