Small Business

Finding the best solution for your business size is our speciality.


Protect your best resource.


For Peace of Mind.


Our group plans are designed to be easy while offering the best product to your employees.

Learn More


The plans provided by our carriers can be custom built to fit any need. Call us today to get started.

Learn More


Self-guided support is available here 24/7. Individual live support is available Monday-Friday.

Learn More

We make it simple.
All benefits plans come complete with Employee and Individual Support Services.

Benefits Specialists
Employee Access
Claims Problems
Health Savings Accounts

Association Medical Coverage

Complete the form linked below to get started.

Yes, there is an app for that.


Many of our carriers have developed mobile apps design specifically to help our customers with their benefit plans. We have compiled a list in our app library. Each item on the list contains a direct link to its download link on the iTunes store for iOS devices or Google+ for Android devices.

Click on the button below to take you to the library.

What our customers say…

Our customers are our fans. We consistently deliver on our promises.

The service we deliver and the products we offer make our clients happy time and again.

“I have very complex and difficult personal insurance needs. I place a premium on ease, simplicity and straight communication. That’s why I’m so pleased with  Chesapeake Benefits. They placed everything I was looking for in a prompt and responsive manner.” Herbert Ford


When we  made decisions to change carriers or our plans, those decisions are not only based on what we believe the carrier can provide us, but also on the fact that we know Chesapeake Benefits will be a part of the relationship. Dolores Gorgone

Chief Financial Officer, The Aspen Institute

(410) 778-9008

860 Washington Ave

Chestertown, MD 21620

We will call you.

Our Services

Life and A.D & D.
Short Term Disability
Long Term Disability
Long Term Care