
"Recommendations from friends are a must when it comes to a sitter for my kids. UrbanSitter has expanded our network of babysitters, and it has given us peace of mind."
Matt K., dad of two

Browse background checked babysitters near you in Winchester. Compare local reviews, rates, and experience to find the right fit.
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Families in Winchester use UrbanSitter for date nights, after school help, and last-minute babysitting.
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I have always enjoyed working with children and began babysitting for family and neighbors during high school and college, both on a part-time and occasional basis. These experiences gave me the chance to care for kids of different ages, from toddlers to school-aged children, and helped me develop patience, creativity, and responsibility. I truly love spending time with children, whether it’s helping with homework, reading stories, playing games, or just keeping them engaged in fun and safe activities. Families describe me as caring, dependable, and attentive, and I pride myself on creating a positive and safe environment. In addition to childcare, I’m comfortable assisting with light household tasks and pet care if needed. Overall, I see babysitting as more than just a job, it’s an opportunity to support families and be a trusted presence for their children.
Looking for someone to fill in those last minute days or nights? Having a hard time finding a long term nanny but need someone else during the search? I’m available! I am a Freelance Film Production Coordinator looking for some part time work. I am the oldest of 7 children and have always been around kids. I worked at a daycare throughout high school and college, and then was a nanny for several years. Currently, I help to take care of my nieces and nephews (aged 3months - 5years) as needed. I am very comfortable and confident with all ages. First Aid and CPR Certified. References available.
“Kayla was great with both kids. My 4 year old loved talking with her and she had my 2 year old smiling and giggling. We will definitely have her back!”
Hello, my name is Deborah and I am a recent graduate of the University of Michigan, where I obtained my degree in Biomedical Engineering. I currently work as a Biotech Engineer, and will begin my Master's degree in Fall 2026. I have received my Basic First Aid Training and completed the Red Cross CPR certification course. I love showing my love to others through cooking meals and love to read in my free time. In caring for your child, I love to engage them through reading, educational games, puzzles and a lot of time outside. In past roles I've been responsible for meal prep, light housekeeping, school pickup/drop off and overnight care.
Nannied for a family of 4 (full-time) for 15 years. Overnight, Vacations and Daily care. I use a variety of different child-care philosophies (e.g. RIE, attachement, gentle care giving) I would say I am most aligned with “holistic” care-giving. Dependent of what each persons specific needs are. Meeting peoples emotional needs and watching them thrive is a great joy of mine. Full spectrum doula. Newborn and Night Nanny. Confident in gentle sleep training. (not crying it out) I’ve been involved in the homeschool/unschooling community for 15+ years. I have a degree in psychology, specifically behavior modification, and feel confident giving care to anyone with low-moderate needs. I am also a certified yoga teacher and was a lifeguard for many years. I am experienced in light household chores as well as having deep roots in nutrition, specifically anti-inflammatory diets. My personality is generally relaxed but I am fiercely loyal to the children in my care, meaning I need to work with a family that also views their child/children as complete people and treats them with respect. :) Also I appreciate adults who can be forward and up front about their boundaries and what they want from a caregiver.
Hi my name is Cristina, I have a lot of personal experience with taking care of people such as my grandmother and my nieces, I also was a camp counselor for DARTS a camp run by the Boston symphony orchestra where I shared my passion for the performing arts and helped the campers use their creativity to put on plays, create dance choreographies and so much more, when it’s not cold or rainy outside I also like to go on fun adventures to new exciting places around Boston :)
Every babysitter's profile is individually reviewed by UrbanSitter's Trust & Safety team after clearing an annual background check. Rely on reviews from local families to help you find your best fit.

"Recommendations from friends are a must when it comes to a sitter for my kids. UrbanSitter has expanded our network of babysitters, and it has given us peace of mind."
Matt K., dad of two

"UrbanSitter has supported my needs for reliable and joyful sitters. Whether it be for work, recreation or last-minute emergencies, we've made wonderful relationships with local sitters who have become a part of our family!"
Natalie O., mom of five

"UrbanSitter is my go-to for quality sitters! I can book weeks ahead of time or easily find a same-day sitter when in a bind. I even hired a part-time nanny during a daycare transition. Customer service is helpful and babysitters respond in a timely manner."
Laura F., mom of two

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