
"Savannah was very sweet playing with our infant. He was very happy taking a bottle from her, going on a walk, and reading a book."
Talia L., parent

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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 My name is Melinda, What I like most about childcare is being able to make a positive impact on a child’s day. I enjoy seeing their personalities shine as they grow and learn. It’s rewarding to know I can provide comfort, encouragement, and structure while also creating fun, memorable moments.” I’m comfortable with pets and in my past nannying jobs I’ve done food prep, light household chores and picking up And dropping off children. On a few occasions I’ve stayed with the kids as well at there activities which o love doing. I miss the days of my daughter playing sports and dance sessions. Looking forward to creating new experiences.
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 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.
Every babysitter on UrbanSitter completes an annual background check, and every profile is individually reviewed by our Trust and Safety team. See reviews from Winchester parents before you book.

"Savannah was very sweet playing with our infant. He was very happy taking a bottle from her, going on a walk, and reading a book."
Talia L., parent

"Leanna was very sweet and good with our daughter. She played with her, changed her diaper, fed her and all the good things that a newborn needs."
Rachel M., parent

"Was our first time leaving our newborn with a sitter. Emily's calm demeanor put us at ease when we left, and she was great about sending us updates."
Andrea Z., parent

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Browse profiles and read parent reviews for free.
To sign up with Facebook, we need permission to use your email address.
Sharing your friends list is optional, and allows us to connect you with sitters they book and recommend. Nothing will be shared or posted.
See infant babysitters connected to families in your Winchester neighborhood. Know who nearby parents rely on for infant care.
Detailed profiles show each babysitter's infant experience, listed skills, certifications, and qualifications.
Read reviews from local families who have trusted their infant with a sitter. See which babysitters are repeat favorites.
Every babysitter completes an annual background check, and every profile is reviewed by our Trust and Safety team.
Tips for easing your baby into care with a new nanny or sitter.
Average babysitting rates in Winchester and across the country.