
"Amina came and helped us out when our babysitter canceled last minute. She was great with our kids. Even our 11 month old son who has stranger anxiety warmed up to her."
Marie C., parent

Need a sitter on short notice? Winchester families find trusted, background checked babysitters on UrbanSitter.
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Families in Winchester use UrbanSitter for last-minute date nights, schedule changes, backup care, and same-day babysitter needs.
51 available today | Avg hourly rate: $24.47/hr
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Hi my name is Ashley, I am a 1st Dental Student living in Boston. I am offering childcare and pet sitting services. I have been CPR certified for over 5 years. I love babysitting! I have been caring for children since I was 8 years old. I enjoy playing games, tutoring and keeping kids busy. I am open to pet sitting small - medium sized dogs as I have been a dog mom for the past 10+ years.
I am a tutor who thrives on helping k-8 students work more successfully in reading and writing. Special Education and literacy are my background with a solid foundation in The Science of Reading and Guided Reading, remedial reading and writing. I have 20 years of experience and a very nurturing manner. I prepare 3/4 year old with readiness skills for school also. I have several parent and teacher references. My skills include working with beginning, intermediate and advanced learners, mostly special needs learners, mild to moderate and English language learners in reading and writing. I also do childcare with ages three to ten. We work on creative play, storytelling, books, language, behaviors, sports, exercise and more, whatever your child's interests are is okay with me. My fees range according to service providing and number of students/children. I work mostly afternoons and evenings for the school year according to my primary position. I like to work all summer days too. I like to be flexible for you.
Hi there! I'm Allie, and I'm a Boston-based college professor and professional actor. I’m currently on summer break and available for short-term childcare opportunities! A bit about me—I moved to Boston to pursue my MFA in Theatre Education at Emerson College, but before that I lived in New York City, where I worked as a full-time nanny (and professional actor!). I have over ten years of childcare and children's education experience, and I'd love to meet you and your family. As a babysitter, I understand that every child and family is unique. I specialize in working with school-age children, children with severe allergies, children of LGBTQ+ families, high net worth families, and children with extra support needs (Prader-Willi syndrome, autism, ADHD, dyslexia, anxiety disorder, mood regulation disorder). I work carefully with parents to create a customized care plan to help their children thrive socially, emotionally, and academically. And as a professional actor, I also love to have fun and encourage imaginative play! My full resume and references are available upon request. I look forward to connecting with you soon!
“Ali is great and so creative — our girls had the best time. ”
Hello! My name is Joanna. I am originally from Cape Cod and am currently live in the Boston. I hold a Master’s degree in Community Development and Planning (specializing in Youth Development) from Clark University. While I currently work in clean energy, I have over a decade of hands-on experience in education and childcare. Throughout my career, I’ve cared for children of all ages, from newborns to teenagers. My background includes serving as a Youth Counselor at the Worcester Boys & Girls Club, tutoring for a college success program, and providing long-term babysitting and nanny-share support for families across Boston and Worcester. Previously, I served as a mother’s helper for a family with a 1-year-old and a 4-year-old. In that role, I managed morning routines, school drop-offs, tidying, outings to local parks, and occasional date-night care. Coming from a large family with many nieces and nephews, childcare has always been a natural part of my life. I love creating engaging, creative environments where children can explore, learn, and grow. I view caregiving as a mutual exchange where kids learn from me, and I learn just as much from them!
“Joanna is the most caring, calm, wonderful person. Our children love her (and so do we), and run to her each time she arrives because she is such a joy. She's reliable, punctual, responsible, and has a wonderful way with children. I cannot recommend her highly enough!”
Hello! My name is Star and I have been described as a positive, patient, and attentive caregiver. I am a recent graduate of the University of Massachusetts Amherst with my bachelors degree in horticultural science with a business focus. I have worked with Children in many summer camp settings, including two summers at Amherst recreation as a lead counselor. I have also spent much of my young adult adulthood babysitting, taking care of children from ages 2 to 14. I am currently a afterschool teacher at Baker elementary school working with kids from grades one to six. I am reliable and can do household tasks like laundry, cooking, and basic cleaning.

As of October 2026
Babysitters on UrbanSitter are background checked every year, with every profile individually reviewed by our Trust and Safety team.
272 sitters background checked in Winchester, MA
4.9 average star rating from total of 584 reviews in Winchester, MA

"Amina came and helped us out when our babysitter canceled last minute. She was great with our kids. Even our 11 month old son who has stranger anxiety warmed up to her."
Marie C., parent

"She was so flexible and came last minute to help out. The house was really neat when I got home and both kids were asleep. Two thumbs up!"
Jenny S., parent

"Thrisa was amazing! Came over last minute and took amazing care of our 11 month old - including bedtime - she's coming back tomorrow :)"
Jesse D., parent

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Sharing your friends list is optional, and allows us to connect you with sitters they book and recommend. Nothing will be shared or posted.
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