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20 Annapolis Events That Bring Rent-By-Owner Guests to Town

Are you interested in the booming “Rent-By-Owner” business?

 Local Short Term Rentals Continue Popularity

We’ve all heard the story how someone we know rented out their entire home, linens and all, for Navy Commissioning Week(graduation for those of you not from Annapolis). The money they made covered two months of mortgage payments and many times a nice vacation. It’s a win-win for all – the owner is financially rewarded with little inconvenience and the guest gets an entire house for 7-8 family members at a fraction of the cost of a hotel.

This story has grown into a cottage industry here in Annapolis with over 200 homes listed on sites like Airbnb, VRBO and Homeaway.  These homes are available for as few as one or two nights and up to one or two months.  Most owners reside in the home and find somewhere to go when they have a confirmed booking. However, more and more we are seeing furnished homes that are used only as short term rentals.  These homes offer an incredible opportunity for real estate investors to earn large returns.

AA9573638 - Exterior (Front)

For example, our featured home shown above, 106 Linden Avenue in Homewood/Annapolis, is listed for sale at $485,000.  Its within walking distance to West Street, Navy Stadium and downtown Annapolis.  With a 25% down investor loan you’ll have a monthly payment around $2200 which includes PITI.  Click Here for property video and photos.

With premium rental weeks like Navy Commissioning Week($4000), Christmas/NYE($1500) and the two fall Boat Shows($3000 each) the owner could expect to rents in the range of $10-12000.  That covers almost half of all mortgage payments for the year.  With just the most basic marketing you may book a handful of Navy football games, a few weddings and a couple business conferences and the property could quickly pay for itself…while knocking $500-600 off your mortgage principal each month.

Here is our top 20+ Events that bring Rent-By-Owner Guests to Town

  1. Naval Academy Commissioning Week
  2. 6 Navy Football Home Games
  3. USNA Parents Weekend
  4. Annapolis & Eastport Yacht Club events
  5. Annual December Parade of Lights
  6. Northrup Gruman Military Bowl – December 27
  7. US Powerboat Show
  8. US Sailboat Show
  9. Fourth of July
  10. Winter Holiday and New Years Eve
  11. Warrior Events St Patricks Parade
  12. Valentines Day/Weekend
  13. Concerts at Rams Head On Stage
  14. 5 Chesapeake Bayhawks home games at Navy Stadium all Summer
  15. Naptown Challenge Lacrosse Tournament – Mid July – dozens of teams from across the country
  16. HoganLax Summer Exposure Lacrosse Tournament –  Mid June 300 teams from mid Atlantic
  17. Blue Angels Exhibition – late May
  18. Weddings
  19. Business conferences, history buffs and antiquing visitors
  20. Outings and events in nearby DC and Baltimore
  21. Countless other groups and events!!!

Can you think of others?  Please comment below with ones we have overlooked!


If you have questions about this process contact us today. We’re  experienced property investors and we’ve sold over a dozen homes in  the Homewood/Admiral Heights/Navy Stadium area recently.  We can help you locate the perfect property, coordinate excellent financing options and even offer support in furnishing and marketing the home after closing. Contact us today for more info –


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