
"Savannah was very sweet playing with our infant. He was very happy taking a bottle from her, going on a walk, and reading a book."
Talia L., parent
Meet infant babysitters Chestertown families trust, with parent reviews, background checks, and detailed profiles.
Looking for jobs? Apply here.
Meet infant babysitters Chestertown families trust, with parent reviews, background checks, and detailed profiles.
Looking for jobs? Apply here.
Families in Chestertown use UrbanSitter for date nights, newborn care, overnight babysitting, and last-minute infant sitters.
All babysitters shown here are background checked every year. Learn more.
Hello, hello out there! My name is Sarai (pronounced Sa-rah-eeeee). I’m from Baltimore, MD. Serving the Baltimore-Washington area. Currently at capacity with families.
I am the proud mom of two children (one 28, and one 9). My son is with me 50% of the time, and my daughter is off doing her own thing. I miss the times when they were infants/toddlers, and because of that, this seemed like a great solution to fulfill the desire to still spend time with little ones as well as fill the void when my son isn’t home. I love to do crafts, play outside, and go on adventures (this was my son’s term for when we took trips to the zoo, beach for a day, went on a hike, etc.) I am a veteran of the USAF where I served for 5 years as a Russian linguist. I am bilingual in Russian and English, and have enjoyed teaching my son and daughter’s friends the language over the years. I am extremely patient, and have worked with children that have behavioral issues, and can deal with separation anxiety when their parents leave while the child adjusts to me. Lastly, I am incredibly respectful of parent’s rules, routines and structure. I don’t have the attitude that just because I raised and am in the process of raising my children, that “my way” is best. It also helps that I had a “helpful” (read meddling) mother in law who liked to “impart” her wisdom and knowledge for me to apply to my parenting skills. Thank you for taking the time to view my profile- I hope to hear from you soon! Best, Melissa
Hello, my name is Starla and I am an energetic and fun sitter ! Although I am current law student (3L) , I have 10+ years of experience working with children of all ages. I am also pet friendly.
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.
Hi everyone, my name is Daniah and I’m from Maryland. I’m a recent graduate of Mount St. Mary’s University with a bachelor’s of science in psychology and am currently in graduate school at George Washington University for my master’s in school counseling. I offer child care, senior care, and household services. I have years of experience working with children as a Sabbath School teacher, ABA therapist, and caregiver. I’ve supported kids from toddlers to teens, including children with autism, helping them with communication, daily routines, and social skills. I’m also CPR/First Aid certified. I’ve cared for seniors and vulnerable adults—helping with appointments, errands, medication, and daily support—and love being a steady, compassionate presence. I also assist with cooking, cleaning, and other household tasks. I’m dependable, empathetic, patient, and passionate about helping others feel safe, supported, and cared for. Let me know how I can help your family!
Every babysitter on UrbanSitter completes an annual background check, and every profile is individually reviewed by our Trust and Safety team. See reviews from Chestertown parents before you book.

"Savannah was very sweet playing with our infant. He was very happy taking a bottle from her, going on a walk, and reading a book."
Talia L., parent

"Leanna was very sweet and good with our daughter. She played with her, changed her diaper, fed her and all the good things that a newborn needs."
Rachel M., parent

"Was our first time leaving our newborn with a sitter. Emily's calm demeanor put us at ease when we left, and she was great about sending us updates."
Andrea Z., parent
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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.
See infant babysitters connected to families in your Chestertown neighborhood. Know who nearby parents rely on for infant care.
Detailed profiles show each babysitter's infant experience, listed skills, certifications, and qualifications.
Read reviews from local families who have trusted their infant with a sitter. See which babysitters are repeat favorites.
Every babysitter completes an annual background check, and every profile is reviewed by our Trust and Safety team.
Tips for easing your baby into care with a new nanny or sitter.
Average babysitting rates in Chestertown and across the country.