Airbnb Management
Full-service Airbnb management for your short-term rental. Nationwide.
Annapolis, Maryland
In Annapolis, Maryland, guests can find a diverse range of Airbnb accommodations to suit various preferences and budgets. The city offers charming historic homes and colonial-style properties that reflect its rich maritime heritage, often located in the picturesque downtown area. For those seeking a more modern stay, there are contemporary apartments and condos with sleek designs and amenities, perfect for couples or solo travelers. Waterfront properties are also popular, providing stunning views of the Chesapeake Bay and easy access to boating activities. Additionally, cozy cottages and quaint bed-and-breakfast-style lodgings offer a more intimate and personalized experience. Whether visitors are looking for a luxurious retreat or a budget-friendly option, Annapolis has a variety of Airbnbs to cater to different tastes and needs.
In Annapolis, Maryland, short-term rentals like Airbnb are subject to specific regulations to ensure compliance with local laws. Property owners must obtain a short-term rental license, which requires an application process including proof of ownership, a safety inspection, and adherence to zoning requirements. The city imposes a limit on the number of guests and mandates that the property owner or a designated representative be available to address any issues during the rental period. Additionally, short-term rental operators are required to collect and remit a 7% accommodation tax to the city, which is used to support local infrastructure and services. Failure to comply with these regulations can result in fines and revocation of the rental license.
Managing an Airbnb in Annapolis, Maryland, involves several key tasks to ensure a successful operation. Hosts need to focus on maintaining the property to meet high cleanliness and comfort standards, as the city attracts tourists for its historic charm and proximity to the Chesapeake Bay. Effective communication with guests is crucial, from promptly responding to inquiries and booking requests to providing detailed check-in instructions and local recommendations. Pricing strategies should be regularly reviewed and adjusted based on seasonal demand and local events, such as the U.S. Naval Academy's graduation and boat shows. Additionally, compliance with local regulations and taxes is essential, as Annapolis may have specific short-term rental laws. Implementing a reliable system for managing bookings, turnovers, and guest reviews will help maintain a positive reputation and ensure a steady stream of bookings.
Annapolis, Maryland, offers several charming areas ideal for an Airbnb stay, each with its unique appeal. The Historic District is a top choice, providing a quintessential Annapolis experience with its cobblestone streets, colonial architecture, and proximity to landmarks like the Maryland State House and the U.S. Naval Academy. Eastport, just across the Spa Creek Bridge, is another popular area, known for its maritime vibe, waterfront views, and vibrant dining scene. West Annapolis offers a quieter, more residential feel while still being close to downtown attractions. For those seeking a more suburban setting with easy access to nature, the neighborhoods around Quiet Waters Park provide a peaceful retreat with opportunities for outdoor activities. Each of these areas offers a distinct taste of Annapolis, making them excellent choices for visitors.
Annapolis, Maryland, presents a promising Airbnb investment opportunity due to its rich historical charm, vibrant maritime culture, and proximity to major urban centers like Washington, D.C., and Baltimore. The city's appeal is bolstered by attractions such as the United States Naval Academy, historic downtown, and numerous waterfront activities, drawing a steady stream of tourists year-round. The local real estate market offers a range of property types, from quaint historic homes to modern waterfront condos, catering to diverse guest preferences. Additionally, Annapolis hosts numerous events and festivals, such as the Annapolis Boat Shows and the Maryland Renaissance Festival, which significantly boost short-term rental demand. Investors can capitalize on the city's strong tourism sector and relatively high occupancy rates, making it a lucrative market for Airbnb ventures.
As of the latest data, the average Airbnb revenue in Annapolis, Maryland, reflects a dynamic short-term rental market driven by the city's rich maritime history and vibrant cultural scene. Hosts in Annapolis typically see varying revenue figures depending on factors such as location, property size, and seasonal demand. Properties located near popular attractions like the United States Naval Academy or the historic downtown area tend to command higher nightly rates and occupancy levels. On average, hosts can expect to earn a moderate to high monthly income, with peak earnings often occurring during the summer months and during major local events such as the Annapolis Boat Shows. However, it's important to note that these figures can fluctuate based on market trends, competition, and changes in local regulations affecting short-term rentals.
Annapolis, Maryland, experiences a relatively high occupancy rate for Airbnbs, particularly during the peak tourist seasons. The city's rich maritime history, vibrant cultural scene, and proximity to the Chesapeake Bay make it a popular destination, especially in the spring and summer months. During these times, occupancy rates can soar as visitors flock to enjoy sailing events, festivals, and the pleasant weather. Conversely, the winter months see a dip in occupancy as the colder weather and reduced tourist activity lead to fewer bookings. However, the holiday season can still attract visitors, maintaining moderate occupancy levels. Overall, Annapolis's Airbnb market is characterized by its strong seasonal fluctuations, with the highest demand occurring from late spring through early fall.
Why Choose Checkmate Rentals?
Other Property Managers | ||
---|---|---|
Cost | Starting at 15% fee | 25-40% fee |
Guest Communications | Guest response within 10 minutes, 24 hours a day | Sporadic guest communications |
Host Communications | Designated host call in phone line | Bot response assistants |
Insurance | Full damage protection for every reservation | Unreliable insurance coverage |
Contract | No annual agreements | Contract lock-ins |
What you get with Checkmate Rentals
Attract Guests

Listing on all top booking sites
Targeted digital marketing
High-definition photography
Custom copywriting
Manage Details

Dynamic rate-setting technology
Dedicated reservation agents
24/7 guest service
Consistent, professional cleaning
Stocking guest amenities
Payment processing
Take Care of You

Unlimited owner holds
No fixed contracts
Local staff in every market
Inspections and regular maintenance
Guest screening
Optional short-term rental insurance
Get in touch with us.
Checkmate Rentals is a full-service property manager. That means the Airbnb listing, the home, the guest and the work is our responsibility.
Local Team Support
Know that you have a friendly, accessible team right up the road to handle any property needs.
Guest Screenings
Book only the most qualified guests 25 and over who’ll enjoy your home the right way.
Unlimited Owner Use
Block off your vacation days with ease, and enjoy your home as often as you want.
Reliable Property Maintenance
Keep your home running smoothly around the clock with a fast, reliable maintenance team.
Transparent Finances
Transparent Finances Booking payouts get paid directly to you for full financial transparency. We never handle your money.
Fast 24/7 Guest Communication
Make every guest feel cared for with industry best response times of 1-15 minutes day and night.
Marketing
Target, attract & book qualified guests with photography, email marketing, and optimized listings.
Revenue Management
Get the competitive edge with dynamic pricing and rates optimized daily by your pricing manager.
Direct Bookings
Earn more year after year as guests book their stay directly on our website.
Housekeeping
Make the perfect first impression with wall-to-wall cleanings before guests arrive.
Inspections
Know your property is guest-ready is top-to-bottom inspections after every booking.
Guest Damage Coverage
Save more when you let us cover accidental guest damage coverage up to $3k.
Smart Home Management
We manage your digital locks & noise monitoring tech in your home.
Fast Listings
Get your home fully listed and ready for guests in as little as 3 days.
Automated Touchpoints
Give guests a seamless experience with automated touchpoints from booking to checkout.
Owner Portal
Stay in the loop on your property with our easy-to-use owner portal that lets you check everything you need.
