Renting Your Annapolis Home for Commissioning Week 2027: An Owner’s Guide

Updated October 2026. A practical guide for Annapolis-area homeowners. Rules summarized here come from public City of Annapolis and Anne Arundel County information. It is not legal advice, so confirm the details with the City or County before you list.

Every May, the U.S. Naval Academy’s Commissioning Week brings thousands of families to Annapolis, and hotel rooms near the Yard sell out a year or more ahead. That makes it the single best week of the year to rent a home in town. Many owners who would never run a year-round Airbnb still rent for this one week and earn a meaningful sum from it. Here’s how to do it right for 2027.

Why Commissioning Week is different

• Demand is guaranteed. Graduation happens every year, and families plan around it months in advance.
• Guests book early. Many families start looking the summer before, so homes listed in the fall have the most choice of guests.
• Guests are a good fit for homeowners. Most groups are parents, grandparents and siblings of a graduating midshipman, there for the ceremonies.
• Location matters more than usual. Walking distance or a short drive to the Academy, plus parking, are what families ask about first.

Do you need a license to rent for just one week?

It depends on where the home is:

• Inside Annapolis city limits: the City allows rentals limited to Commissioning Week and the spring and fall boat shows with a free City registration instead of a full short-term rental operating license. That matters in 2026–27, because the City has paused most new non-owner-occupied licenses.
• Outside city limits (for example, Bay Ridge, Cape St. Claire, Arnold or Severna Park): Anne Arundel County’s short-term residential rental registration rules apply.

Not sure which side of the line you’re on? A mailing address that says “Annapolis” doesn’t settle it. Our Annapolis short-term rental license guide walks through how to check, and covers the full rules.

Taxes still apply

Commissioning Week stays are taxable like any other short-term rental: Maryland’s sales and use tax and Anne Arundel County’s hotel occupancy tax apply to stays of 120 days or less. Airbnb and Vrbo collect and remit for their own bookings. Direct bookings are your responsibility, so keep records and file on time.

A 6-step plan for owners

1. Confirm your jurisdiction and register. Start with the City or County, depending on where the home sits.
2. Decide your dates. Most families want the full week around graduation, and many want a minimum stay that covers the main events. Block the whole stretch so you aren’t left with awkward gap nights.
3. Get the house guest-ready. Beds and linens for every sleeping spot, a stocked kitchen, fast Wi-Fi, clear parking instructions and a secure place for your personal items.
4. Check your insurance. Ask your homeowner’s insurer whether short-term rental guests are covered, or add a rental policy.
5. Price for the week, not the night. Commissioning Week rates run well above normal Annapolis rates. Look at what comparable homes near the Academy are asking, and set a deposit and cancellation policy that protects you.
6. Plan the turnover. You’ll need a professional clean before and after, someone local for anything that breaks mid-stay, and a smooth check-in for guests who may arrive late after a long drive.

Do it yourself, or have it handled

Some owners rent their home themselves for the week. Others prefer to hand off the listing, pricing, guest screening, registration, taxes, cleaning and on-call support, so the only thing they do is hand over a key. The House Kee manages homes in Annapolis and Anne Arundel County year-round and for Commissioning Week, with a local team on the ground and trust accounting on every owner account.

See what your home could earn for Commissioning Week

Or learn more about Annapolis vacation rental management with The House Kee.

Frequently asked questions

When is Commissioning Week 2027?

Commissioning Week takes place in late May each year. The Naval Academy publishes the official schedule, so check it before you set your dates.

Can I rent my Annapolis home only for Commissioning Week?

Yes. Inside city limits, rentals limited to Commissioning Week and the boat shows need only a free City registration rather than a paid operating license. Homes outside city limits follow Anne Arundel County’s registration rules.

Do I have to pay taxes on a one-week rental?

Yes. State sales and use tax and the County hotel occupancy tax apply to short-term stays. Airbnb and Vrbo remit for their bookings. You’re responsible for direct bookings.

How far ahead should I list my home?

As early as you can. Many families start searching the summer and fall before graduation, and the best-located homes book first.