Self-Employed Health Insurance in Vermont (2025)

Introduction
This guide is designed for freelancers, sole proprietors, gig workers, and anyone managing their health insurance without an employer. If you’re self-employed in Vermont, finding the right health insurance plan is a crucial part of managing your business and personal finances. From artists and consultants to farmers and part-time entrepreneurs, Vermont offers a range of affordable options tailored to your needs.
Vermont-Specific Considerations
Vermont’s rural geography can make access to providers and specialists more limited in some regions. If you live in a less populated area, it’s worth checking whether telehealth is included in your plan and whether you need access to out-of-state networks. PPOs are often a better fit for those needing care beyond Vermont’s borders.
Tax Tips for the Self-Employed
Self-employed Vermonters may qualify to deduct 100% of their health insurance premiums from federal taxes. If you enroll in a high-deductible health plan (HDHP), you may also contribute pre-tax dollars to a Health Savings Account (HSA). These savings accounts allow you to cover future medical expenses while lowering your taxable income.
Why Health Coverage Matters
Being uninsured, even temporarily, can be a serious financial risk. A single medical emergency could derail your income and savings. Having consistent coverage ensures access to preventive care, mental health services, and essential prescriptions, so you can stay healthy and focused on your work.
Top Coverage Options for Vermont’s Self-Employed
- Private PPO & EPO Plans: Access larger networks and out-of-state providers with more flexibility.
- Marketplace Plans via Vermont Health Connect: ACA-compliant coverage with subsidies based on income.
- Catastrophic or High-Deductible Plans: Lower monthly premiums, ideal for those with few medical needs.

Who Qualifies as Self-Employed?
You’re considered self-employed if you run a business without employees or work independently. This includes:
- Freelancers and gig workers
- Independent contractors (1099)
- Sole proprietors and single-member LLCs
- Part-time entrepreneurs without W-2 staff
How to Choose the Right Plan
When evaluating plans, consider your provider preferences, expected medical needs, and travel habits. If you often cross state lines or want to see a specific doctor, a PPO may be worth the higher premium. If you prioritize lower premiums and don’t need out-of-network care, an EPO could be ideal. Also, weigh deductible levels against monthly costs to balance your budget and risk.
Common Vermont Carriers
Popular insurers in Vermont include Blue Cross Blue Shield of Vermont and MVP Health Care. PPO plans from national carriers may also be available through private broker channels. These can be a good fit if you’re seeking broader networks not available through Vermont Health Connect.
Enrollment Deadlines
Open enrollment typically runs from November to January, but you may qualify for a Special Enrollment Period (SEP) if you’ve experienced a life event like leaving a job, relocating, or starting your business. Check Vermont Health Connect for the most up-to-date deadlines.
Subsidies and Financial Assistance
Many self-employed Vermonters qualify for premium subsidies through Vermont Health Connect. These are based on income and household size.

Real-World Examples
Consider these examples to see how other Vermonters choose coverage:
- Emma, a self-employed artist in Montpelier, qualifies for a Silver plan with subsidies through Vermont Health Connect.
- Ben, a freelance software developer, chooses a national PPO to maintain access to out-of-state specialists.
- Sophie, a single mom running an Etsy shop, qualifies for cost-sharing reductions and selects a Gold-tier plan.
- Dan, a seasonal landscaper in rural Vermont, selects a Bronze HSA-compatible plan to keep premiums low during the off-season months.
Helpful Links
- Vermont Health Insurance (State Page)
- Affordable Plans in Vermont
- Nationwide PPO Plans
- Best PPO Plans for Freelancers
Frequently Asked Questions
Can I deduct health insurance premiums as a self-employed person?
Yes. You may be eligible to deduct 100% of your premiums on your federal taxes if you meet IRS requirements.
Can I use an HSA with my plan?
Only high-deductible health plans (HDHPs) are HSA-eligible. If you enroll in one, you can contribute pre-tax dollars to cover qualified medical expenses.
What if I move between states?
If you’re relocating, you may qualify for a Special Enrollment Period and can switch to a plan in your new state of residence.
What if I earn too much for subsidies?
You can still purchase a plan off-exchange, including PPO or EPO plans, through licensed brokers or insurers directly.
Do I have to use Vermont Health Connect?
No, you can compare private options outside the marketplace if you don’t qualify for subsidies or need broader networks.
Still Unsure? Talk to a Vermont Broker
Choosing the right plan can feel overwhelming, especially with so many options. Our licensed brokers understand both the Vermont Health Connect marketplace and off-exchange private options. We’ll help you compare plans based on your income, network preferences, and whether you’re looking for family or individual coverage.
Get Expert Help Today
We specialize in helping self-employed Vermonters like you find the best possible coverage — whether through Vermont Health Connect or private PPOs and EPOs. Start your quote below or call us for personalized advice.