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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.

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

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Hannah
Booked by 1 repeat family
1 review
$24 per hour for 1 child
Booked by 1 family in Winchester, MA

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.

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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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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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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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Christine 3 reviews
$25 per hour for 1 child
Booked by 4 families in Winchester, MA

My name is Christinei. I am a professional educator over 41 years now and have been a nanny for about 22 of those. This was the best decision I made ever. I like the one on one care it provides for the child(ren) and the whole family, including pets. Each child is an individual and needs to be heard and learns differently and this as an educator is where I learn from them. My expertise is in newborn/infant/toddler care but I also love to prepare your child for preschool and readiness for group learning environments. I teach through all experiences and will help the new parent “see” each developmental level their child has experienced and help achieve the next level with proper fun experiences - yes a three month old can “read” a favorite book! I look forward to becoming part of your child’s team - that includes the love of the family pet!

Christine first joined our network about 8 years ago as we became new parents. We needed help a few days a week as I (mama) worked from home. She very much followed my lead, allowed me to have my time with my newborn sitting back and chatting and sharing little tidbits that became so helpful when navigating new parenthood - but when I needed to step away and dive into work-focus, she was able to keep space and handle whatever was happening. Her specialized education in language development quickly became apparent. She would have the most delightful conversations with our infant, and then focus in on age appropriate sounds for language development. They were soon chatting for hours while working with playdoh and doing art. It was a joy to see. When I had to work out of the house, I always came home to a journal review of food, activities, new language development, and all the things a new parent wants to be up to speed on. She bubbled up with us during the pandemic while I was pregnant with our second baby, she was with us full time - allowing us bonding time with our new baby and keeping our toddler engaged and with a routine that could be as consistent as possible during uncertain times. She also brought our lovable dog and cat into her “classroom routines”. She is what we call our “Forever Nanny” - we still consistently use her for date nights, weekends away — and we’ve even gone out of the country for 5 days and left our most loved beings (kids and pets) in the care of Christine. She also takes our fur-babies for us if needed, and she shows up for all the dance recitals and birthday parties. Christine makes learning fun for the kiddos and knows how to set boundaries. She is open to shifting style, depending on family philosophy, but she is also confident enough to offer a different perspective if appropriate. She sets a daily routine consisting of all the normal things (eating, diapering/bathroom) + art (she’s a wonderful and fun artist - it’s one of our kids’ favorite things to do with her), reading, writing, math, gross motor skills, neighborhood adventures, music (I’m probably forgetting others) - but it’s fun and balanced! Christine is a gem.

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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.

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?

Babysitting rates in Winchester 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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