Common Questions about Annapolis Vacation Homes

How do I book a home?
You can either make a booking directly on this website by using the "check availability box" to the left. Or you can email us at [email protected] or call our office at 301-502-7073 and a reservationist will be glad to help you.
Is booking online secure?
We implement a variety of security measures to maintain the safety of your personal information when you place an order. We offer the use of a secure server. All supplied sensitive information is transmitted via Secure Socket Layer (SSL) technology and then encrypted into our payment gateway providers database. It will only be accessible by those authorized with special rights to such systems. They are required to keep the information confidential. After a transaction, your private information (credit cards, social security numbers, financials, etc.) will not be stored on our servers.
Can I bring my pet with me?
We offer several homes, some of which allow pets and some do not. You can either look at our properties online by clicking on the "vacation rentals" tab above and see if the home you are looking at allows pets. You can also email us at [email protected] or call our office at 301-502-7073 and a reservationist would love to help find a home that is just right for you and your pet.
What are the benefits of a vacation home rental?
Our vacation homes are stocked in such a way that you always feel like you are coming "home" to your "vacation home" rather than returning to a small hotel room. Our homes have full kitchens, with some homes having other amenities such as hot tubs, game rooms, pools, and grilling areas. You will be able to enjoy a full-service home while you are on vacation rather than a small hotel room.
Commissioning Week
1: Start by clicking on the appropriate Commissioning Week year button above. When you find a home you are interested in, you can email us directly through the "Contact an Agent" button on the property details tab or, if you have interest in more than one property, you can gather the property codes and include them in the contact form comments section. 

2: Once we receive the property codes you are interested in we then send you the owners' contact information to discuss the property and/or make arrangements to see the property more in-depth. Some families arrange their mid to see the property if they are not able to do so themselves. Be sure to discuss all the details of your stay with the owner including the number of people, children, pet allergies, desired dates (7-night minimum, see above for dates), special needs, and most importantly the kind of party or entertaining that they will permit.

3: After speaking with the owner and deciding on a property, you then contact us to proceed with the paperwork and payments.
Please keep in mind that 50% of your payment is due within one week of making the reservation. The remaining balance and Damage Deposit are due in the month of January of the graduation year. Rates do not include 6% Maryland Sales Tax for stays of 30 days or less. 

When should I book my property?
There is no 'best' time to book a house other than when you see the one you want here on the website! We post initial availability close to two years in advance and have our maximum availability the Summer and Fall before the graduation year. In-town and waterfront homes will be booked quickly, but there's always a generous selection of homes throughout the Annapolis area. If you're a world class procrastinator, it's a safe bet that you can choose an excellent house even in early May before graduation!

Where are these homes located? 
View our Neighborhood Map to see the general location of our properties. Homes within walking distance tend to be small and expensive, and lack off-street parking. You get much more house for your money with options just a few miles away. Many of our properties are located within walking distance of the Academy, in Homewood, Admiral Heights, Stadium District, and West Annapolis neighborhoods. We also have homes in the outskirts of Annapolis (Severna Park, Arnold, Eastport, and Davidsonville) to accommodate larger groups. We also include a Community Info tab for each of our properties. Click on the tab to see a list of stores and restaurants near each property.