
"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.
46 available tonight | Avg hourly rate: $24.47/hr
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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!”
I really like and generally have a very good rapport with most children (toddlers, especially) and have experience baby sitting and taking out for entertainment events several generations of nieces, nephews, grand-nieces & nephews, Enjoy reading, theatre/dance/music concerts and cultural events/venues, stories & re-enacting characters with and for children. I've worked in the past at the Wheelock Family Theatre and have worked as costumed characters in holiday events, especially (e g. X-Mas Elf at Filene's and Macy's; Mouse King in Boston Ballet Nutcracker promos, etc. Also, I'm a dog-lover .... have a good "rapport" with them, too. Many dogs I don't know will approach me for friendly attention while being walked. It appears - like children - that they have a "sixth sense", too. I'm also able to take on occasional office-support, general cleaning, and small special projects. I work PT and remotely from home in B2B sales and marketing. As my schedule can be somewhat flexible, I occasionally have open times for baby sitting, generally in the late afternoon, evenings, on some weekends, and - when remote work is slow - sometimes earlier in the day on weekdays.
Hello! My name is Teagan and I have been working with kids of all ages for about 11 years. I have experience working with children from ages 0-16. Please reach out if you have any questions! Thanks!
“Teagan looked after my son (four and a half months old) during the day while I ran some errands. She was energetic when she walked in and it was clear she knew a baby of his ages rhythm. Luca didn’t take a long nap like he typically does by Teagan was able to calm him down and do some more chilled playtime. She was also communicative throughout the day.”
Hello! My name is Hanna. I have an educational background and come from Belarus. I speak 3 languages Russian, German a bit and English. Hands on experience taking care for 1-2 kids at the same time, college educated, CPR trained, Newborn Care specialist certificate, good w animals and kids Friendly and responsible, can help w light babyrelated housekeeping, cleaning play areas or doing laundry for the baby. Meal prep. Have an experience working as a night nanny, live- in nanny, travel nanny , sick days nanny Looking forward to meet you!
Hi! My name is Lilah and I am a freshman at Berklee College of Music with a lot of free time that I would love to spend getting to know my community. I have been babysitting kids ranging from ages 3-15 for 2 and a half years along with my two younger sisters who are now 12 and 15. I love spending time with kids singing karaoke, making fun snacks, doing arts and crafts, and playing games (my personal favorite is uno). I also would be more than willing to help out around the house whether that’s cleaning, running errands, or cooking delicious and nutritious meals!

As of October 2026
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.
272 sitters background checked in Winchester, MA
4.9 average star rating from total of 584 reviews in Winchester, MA

"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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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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