
"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

Planning a wedding or attending one in Chester? Hire babysitters loved by local families. Browse profiles and see who's available for free.
Looking for jobs? Apply here.
Families in Chester turn to UrbanSitter for wedding and special event babysitting.
All babysitters shown here are background checked every year. Learn more.
Hi there! I’m Amanda; a longtime caregiver, former au-pair/nanny, and a single mom of two wonderful kids. Alongside my main work as a consultant, I also serve as a substitute teacher for AACPS, and help coach local kids sports, so I’m used to adapting quickly and connecting with children of all personalities and ages. I work from home most days, which gives me flexibility to help local families with babysitting, after-school care, or date nights. Whether it’s keeping little ones engaged with activities, helping with homework, or making sure evenings run smoothly, I focus on creating a safe, calm, and positive environment where kids feel comfortable. I'm an energetic, dependable, patient, and easy going Australian, and genuinely enjoy being with kids. I’m also happy to lend a hand with light household tasks or pet care when needed. Available for flexible bookings in Edgewater, Annapolis, and nearby areas; open to evening or occasional weekend jobs when my schedule allows.
Hello! My name is Georgia! I have been baby sitting for 3 years now! I have been working with kids from the ages of 3-12 for about 4 years now as a gymnastics coach. I also serve in children’s ministry at my church every Sunday. I am the second oldest in a family of five! I am very understanding and interactive with kids!
I'm a college student, just finished with my freshman year at Florida State University, and someone who has a genuine passion for caring for kids. I am both First Aid and CPR certified, and ready to create a fun and engaging environment that supports your family's needs. I have experience babysitting for events such as weddings, working at a summer camp, volunteering as an elementary school helper, and also assisting friends and family with childcare. Whether it's creating arts and crafts, doing homework, playing fun outdoor games, or creating meals together, I am ready to help kids learn and grow. I have my own car, have experience with children of all ages and caring for pets as well. Feel free to contact me for references or to set up a call!
Hello - My name is Furaha I genuinely enjoy working and babysitting children. I have worked in Pediatrics office for about a year. Additionally I have babysat for various families for 3 years now. I am a Medical Assistant and certified in CPR and first aid. I have extensive knowledge of medical child care needs. Furthermore I am a college tutor and speak 3 Languages. I am able to help out particularly in STEM. I am extremely active and athletic and can help with sports, specifically basketball and tennis. I do pride myself in my cooking skills and can make a mean omelette and grilled cheese.
“Very kind, reliable and understanding. Great with my son.”
Hi families! I'm a 4th grade teacher in my third year of teaching, with over 8 years of experience caring for children of all ages. I have a degree in Elementary Education and am also a certified tutor. I love bringing both fun and learning into my time with kids. I'm reliable, patient, and genuinely passionate about helping children feel safe, supported, and engaged. Whether your child needs homework help, creative play, or just a calm, trusted presence I’m here for you!
“Very Prompt. The kids loved her! 10/10!”
Every babysitter on UrbanSitter completes an annual background check, and every profile is individually reviewed by our Trust and Safety team.

"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

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.

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.