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Find a wedding babysitter in Winchester, MA

Planning a wedding or attending one in Winchester? Hire babysitters loved by local families. Browse profiles and see who's available for free.

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58 experienced babysitters in Winchester, MA

Families in Winchester turn to UrbanSitter for wedding and special event babysitting.
45 available tonight | Avg hourly rate: $24.68/hr

All babysitters shown here are background checked every year. Learn more.

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Stephanie
Booked by 49 repeat families
57 reviews
$35 per hour for 1 child
Booked by 105 families in Winchester, MA

Hello, my name is Stephanie and I am a current Teacher in Boston. I graduated from UMB majoring in Early childhood Education and English as my bachelors and Elementary Education as my Masters. I’ve been babysitting since I was 14 with nieces, nephews, friends little siblings and even my coaches kids. I have experience ranging from infants all the way to 13 year olds. I can help with homework, cooking food and creating a positive environment for your kids. I’m also pet friendly and have taken care of pets in the past! Outside of urban sitter I’m a full time classroom teacher which has helped me be more concious of creating a safe space and helped me take pride in my work with Restorative Justice practices. I hope to hear from you soon!

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Clara
Booked by 2 repeat families
2 reviews
$25 per hour for 1 child
Booked by 2 families in Winchester, MA

My name is Clara . I am currently a Teacher’s Assistant for toddlers and infants. I have worked in this field for a year now and I am working full time. In addition to working full time, I am a student at Bunker Hill Community college. By the end of this semester, I will receive my certificate in early education. I am looking for a part-time job where I can continue working with the kiddos and learn, hoping to gain enough experience to become a lead teacher and have my own classroom in the future. I have several certifications such as -First Aid/ C.P.R , Safe Sleeping Practices, Emergency Response and Medication Administration. Thank you for considering me to take care of your kiddos! Clara

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Scarlen 5 reviews
$25 per hour for 1 child
Booked by 4 families in Winchester, MA

Hello I’m Scarlen! I am a Licensed Nursing Assistant at Massachusetts General Hospital and have six years of experience working with children from 7 months to 14 years old. I am fluent in Spanish and passionate about providing safe, attentive, and nurturing care while building positive connections with children and families. I am certified in Basic Life Support (BLS) and CPR, allowing me to respond quickly and responsibly in emergency situations. I bring patience, creativity, and structure to every environment, helping children feel both supported and engaged with. Outside of work and school, I enjoy traveling, nature, and spending time with my younger siblings. I would be happy to get to know you and your family better and provide support in any way you may need.

“Our two little boys loved Scarlen! She was prompt and communicative, very positive and kind with the boys, and she was playful while in control. They took to her instantly and got to bed without issue. She’s a wonderful sitter!”

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Mei 2 reviews
$30 per hour for 1 child
Booked by 1 family in Winchester, MA

Hello everyone, my name is Mei. I’m a 26-year-old full-time mental health therapist with a Master’s degree in Clinical Mental Health Counseling. I work with clients of all ages, but I have a special passion for working with children and young adults. I’ve been a nanny and babysitter on and off for the past 6 years for children ranging from 10 months to 12 years old, and I have experience caring for up to three children at a time. I’m CPR certified and have a reliable new car. I have additional trainings and certifications related to supporting children’s emotional and mental well-being. I bring a calm, patient, and caring approach to childcare and really value meeting children where they are. My professional experience has given me a strong understanding of child development, communication, emotional regulation, and creating a safe and supportive environment for kids. I’m currently looking for part-time or occasional babysitting opportunities, including date nights, weekend care, or other occasional childcare needs. As the cost of living continues to increase, I’m hoping to use my childcare experience to earn some supplemental income while continuing to do something I genuinely enjoy! When I’m babysitting, I love getting to know each child and finding activities they genuinely enjoy. I’m always happy to get creative with arts and crafts, read books, play outside, or come up with fun indoor activities. I believe babysitting should be more than simply supervising children. I want kids to feel comfortable, heard, and engaged while their parents are away. I’m also happy to prepare simple meals or snacks when needed and help with light tidying related to the children. Most importantly, I want parents to feel confident that their children are in caring, responsible, and capable hands. I’d love the opportunity to get to know your family and help make your time away from your little ones as easy and stress-free as possible!

“Mei has been an incredible addition to our family, consistently demonstrating patience, reliability, and a genuine warmth with our children. Her ability to handle daily routines while keeping the kids engaged in creative activities has been a huge relief for us. We recommend her without hesitation to any family looking for a trustworthy and nurturing caregiver.”

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Amanda
Booked by 1 repeat family
$20 per hour for 1 child
Booked by 1 family in Winchester, MA

Hi! My name is Amanda, and I have extensive dog care experience. Having grown up with a lab/hound mix, and caring for friends' and family's pets since, I am comfortable and familiar with dogs of all shapes and sizes. I love taking dogs for long walks, giving them treats, and making sure they are safe and having fun at all times!

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How much does a wedding babysitter cost in Winchester, MA?

  • Average hourly rate for 1 child: $24.68
  • Average hourly rate for 2 children: $29.90
  • Typical job length: 4.3 hours
  • Most requested times: Afternoon

As of November 2026

Recent babysitter activity in Winchester, MA

Hiring a wedding babysitter starts with trust

Every babysitter on UrbanSitter completes an annual background check, and every profile is individually reviewed by our Trust and Safety team.

262 sitters background checked in Winchester, MA

4.9 average star rating from 633 reviews in Winchester, MA

photo of quoted parent Madeleine

"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

stock photo of a 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

photo of quoted parent Catherine

"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

Family with caregiver

Find a wedding babysitter in Winchester

Browse profiles and read parent reviews for free.

Why Winchester families use UrbanSitter for wedding child care

Easy to start, no pressure to hire

Share the wedding date and babysitting details, then hear from available sitters. Review your options and hire only if you find the right fit.

Your choice of sitter

Browse profiles, read reviews from other parents, and pick the babysitter you feel best about. No agency assignments.

Background checked, every year

Every babysitter completes an annual background check. See bookings, repeat families, and reviews from local parents.

Hotel, venue, or overnight

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.

Frequently asked questions about wedding babysitters in Winchester

How do I find a wedding babysitter in Winchester?

Share the wedding date, location, times, and number of children you need care for on UrbanSitter. Available babysitters in Winchester can respond, and you can browse profiles and set up a phone interview before booking. There is no obligation to hire unless you find a fit.

How much does a wedding babysitter cost in Winchester?

As of November 2026, babysitting rates in Winchester average $24.68 per hour for one child. Rates vary by experience, number of children, and job length. For special occasions or longer bookings, some families offer a higher rate. See average babysitting rates in your area.

Are babysitters in Winchester on UrbanSitter background checked?

Yes. Every babysitter on UrbanSitter completes an annual background check, including those in Winchester. Each profile is individually reviewed by our Trust and Safety team. See what's included in the background check.

Can a babysitter watch kids at the hotel or wedding venue?

Yes. When you share your care needs, include the care location, whether that is a hotel room, a kids' room at the venue, or somewhere nearby. Many babysitters in Winchester are comfortable with both on-site and off-site care. Let the sitter know about any planned activities so the kids stay entertained while you enjoy the celebration.

How far in advance should I book a wedding babysitter in Winchester?

Two months out is a good starting point to look for a wedding babysitter. That gives you time to browse candidates, read reviews, and schedule an interview if you would like to connect before the event. UrbanSitter also works well on shorter timelines.

What if I am not from Winchester and need a wedding babysitter?

Whether you are attending a destination wedding or visiting Winchester for the celebration, you can use UrbanSitter to find a wedding babysitter. Start by submitting your request, and available babysitters in Winchester can respond. Next, browse profiles and read reviews from local families to find a fit. You can also schedule a phone or video interview before your trip for added peace of mind.

Resources

Preparing for your first babysitter

Tips for handing off your children to a new sitter.

Top questions to ask a babysitter in an interview

The top questions to ask when choosing a sitter.

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