
"Katrina watched our son while we were in town for a wedding. She was timely, so nice and sent great pictures throughout the evening. He looked like he was having more fun than we were!"
Madeleine B., parent

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46 available tonight | Avg hourly rate: $24.63/hr
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Hi! My name is Kay, and I’m a student at Emmanuel College in the Fenway area, where I’m pursuing a degree in Elementary Education. I have about three years of hands-on experience working with children from kindergarten through 8th grade, and I currently work in both pre- and post-school day programs as well as summer camps. Additionally, I have experience babysitting younger children, ages 2–4. Working with kids is truly my passion. My goal is to provide a safe, positive, and caring environment where children feel supported and engaged. I take pride in being patient, attentive, and responsible, and I always strive to make each child’s time with me fun, meaningful, and secure. I also have over five years of experience pet sitting both large and small dogs, as well as cats. I’m more than happy to take on household pet responsibilities, including feeding, walking, and providing attentive care while you’re away.
Hi families! I'm Aniyah, and I'm currently looking for part-time babysitting position. I'm a certified babysitter with First Aid, CPR, and BLS Certifications, and I truly enjoy working with children - whether that's helping with homework, planning fun activities, or keeping routines smooth and stress-free for parents. I also handle Lighthouse cleanup and meal preparation. I'm responsible, patient, and big on safety and communication. My availability is Monday, Wednesday, and Thursday from 12-6, and I'm open to recurring or Occasional positions or speaking about different times. Please feel free to reach out if you're looking for a sitter and have any questions. Thank you 😊!
Hello, I am Maliyah. I am 20 years old. I just moved to massachusetts in early November of 2025. I am originally from new york. I worked as a teaching assistant back in New york. I also am the eldest siblings with the age gap being over 10 years. I’d say i have lots of experience with different ages between 2-15. I am excited to start working with you.
Hi there! By day, I work in tech, but I’ve never stopped missing spending time with kids. In college, I babysat, tutored, and coached a girls’ soccer team, and I also spent a summer as a camp counselor. I’m still in touch with some of those families today, which means so much to me. I love getting to know each kid’s personality, cheering them on, and being a good mentor — and a little bit of an older sister, too. I’m happy to help with homework, explore the city, do crafts, play games, or wind down with a calm bedtime routine. I’d love to get to know your family and hopefully become someone your kids look forward to spending time with!
I’ve worked as a pre-k teacher for the past 4 1/2 years, frequently babysit and used to have 2 nannying jobs. I’m pretty decent with special needs kids and have worked with them before. I have been CORI checked, have no criminal background and am CPR, First aid and teacher certified. I’m playful and creative with children and encourage learning, boundaries, playing pretend, creativeness, and just fun all around! I am experienced, ambitious, organized, a good listener, / great rule/boundary follower, and kind, respectful, accommodating, outgoing and energetic. I’ve mainly only watched children but have also watched pets before. I have no experience watching seniors but am willing to learn and do it. I’ve also never house-sat but am again, willing to and am very responsible and great at cleaning and taking care of things and keeping it in check. I have a background with psychology and social work from college so I’m very good at reading children’s heads and understanding their personalities. I am also very protective of them because of my schooling in social work so I know how to watch and take care of them. I am currently going to college for nursing and am doing multiple interviews for more teaching positions at other schools because I recently got laid off because there was too many staff members.

As of November 2026
Every babysitter on UrbanSitter completes an annual background check, and every profile is individually reviewed by our Trust and Safety team.
264 sitters background checked in Winchester, MA
4.9 average star rating from 633 reviews in Winchester, MA

"Katrina watched our son while we were in town for a wedding. She was timely, so nice and sent great pictures throughout the evening. He looked like he was having more fun than we were!"
Madeleine B., parent

"Caitlin was awesome and jumped right in to chaperone four girls (10, 9, 8 and 6) at a family wedding (they were bridesmaids) and she was very helpful with the event as well as taking them home and putting them to bed."
Lila P., parent

"McKenna was great with our 3 year old son! She came prepared with a box of fun activities and handled playing, dinner, and bedtime seamlessly... and it was all at our hotel while we were in town for a wedding. Thank you McKenna!"
Catherine B., 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.
Share the wedding date and babysitting details, then hear from available sitters. Review your options and hire only if you find the right fit.
Browse profiles, read reviews from other parents, and pick the babysitter you feel best about. No agency assignments.
Every babysitter completes an annual background check. See bookings, repeat families, and reviews from local parents.
Whether it is a hotel room, a kids' room at the venue, or late-night care, book one sitter or several to fit the plan.