Chestertown, MD Babysitting Jobs

Looking for Chestertown babysitting jobs? Earn extra cash by helping extra nice families with UrbanSitter. Apply today for occasional babysitting gigs, part-time or full-time babysitting jobs!

Available babysitting jobs in Chestertown, MD

Hiring a babysitter Wednesday, Jul 16 at 6:00 PM - 11:30 PM in Benning Heights

Looking for someone to provide care every other week for my little one. The days will vary but mainly fall a Monday, Wednesday, or Saturday evening.

Sitter job available Saturday, Jul 19, 6:00pm - 11:00pm

We’re looking for a fun, creative sitter for our two kids on July 19th, 2025. We’ll be at Hyatt Regency Chesapeake Resort in Cambridge for a family event. Kids are 5 and 9 yrs old and should stay in...

Sitter position available Saturday, Jul 19, 6:30pm - 11:30pm in Burnt Mills

We are looking for a babysitter for our 23 month old on the evening of July 19th. We are looking for someone who can come by and meet and play with our son for a bit and then we will do the bedtime...

Part Time nanny job available starting Monday, Jul 21 (flexible) in Deanwood

I work from home and am looking for a part time caretaker in home for my baby for when I work and step out for errands. We can discuss baby’s routine upon hire! Thank you for your consideration.

Sitter needed Saturday, Jul 26, 7:30am - 1:30pm

Looking for someone to watch my daughter while I work on Saturday mornings she will more than likely be asleep most of the time

Seeking an experienced part time caretaker starting Monday, Jul 28 - $25/hr

Hello! We are looking for a sitter for our 8 year old Lukas. He is energetic and creative. He likes gaming, puzzles, learning languages, agility, and a list of other things. He has ADHD and Anxiety...

Family looking for a part time caretaker starting Monday, Jul 28 (flexible) - $17/hr

Looking for a babysitter to sit while I work overnight 11pm - 7am. He usually sleeps through the night .

Family needs a babysitter Monday, Jul 28 at 7:30 AM - Friday, Aug 01 at 4:00 PM

Looking for part time help for getting children to camp and pick up. Need for 1 week in July and then occasional jobs throughout the summer and ongoing.

Sign up for UrbanSitter to apply for Chestertown babysitting jobs

Apply for babysitting jobs now


Ready to find babysitting jobs?

Friends Circle icon
1. Make a profile
Introduce yourself to parents and be sure to include your childcare experience and types of babysitting work you're looking for. Fill in your schedule and rates, and complete a background check.
Briefcase icon
2. Apply to jobs
Easily scan through the available babysitting jobs in your area. Detailed job descriptions and handy search filters help you pinpoint the best babysitting jobs to apply to.
Credit card icon
3. Get paid
Parents either pay in cash or through UrbanSitter's online payment system. Money goes directly into your pocket or into your payout account. No waiting for payday and you keep 100% of your earnings.

Find babysitting work today!


As seen on