Frequently Asked Questions
We’ve gathered answers to the most common questions about staying at Fair Winds. If you don’t see what you’re looking for, feel free to reach out — we’re always happy to help.
About the Property
-
Fair Winds is a fully restored historic home in downtown Annapolis, designed for group stays, family gatherings, and meaningful visits — just one block from the U.S. Naval Academy.
-
The home comfortably accommodates up to 12 guests across five bedrooms.
We also have a Pack & Play available.
-
Yes, guests have full private access to the entire home during their stay.
Sleeping Arrangements
-
Fair Winds includes five bedrooms with a mix of King, Queen, and Twin beds, to comfortably accommodate 12 guests. We also have a Pack & Play available upon request.
2nd Floor: 3 Bed/2 Bath — BR1: 1 King Bed + 2 Twin Sleeper Chairs | BR2: 2 Twin Beds | BR3: 1 King Bed
3rd Floor: 2 Bed/1 Bath — BR4: 1 Queen Bed | BR5: 1 Queen Bed
Booking & Stay Details
-
You can check availability and request your stay directly through our booking page.
-
Yes, we offer a secure and straightforward direct booking experience.
-
The home includes a fully equipped kitchen, linens, Wi-Fi, and all essentials needed for a comfortable stay.
Location & Logistics
-
Fair Winds is located directly in the heart of downtown Annapolis, just one block from the U.S. Naval Academy, two blocks from the waterfront, and easy walking distance to the main shops, restaurants, and historic Capital landmarks.
-
Ample street parking as well as multiple parking garages are available for guests. Given Fair Winds central location, most find walking the preferred method of travel for the local area.
-
The home is highly walkable, allowing easy access to key Annapolis attractions and events.
Commissioning Week
-
Yes — Fair Winds is ideally located just one block from the Naval Academy, making it an excellent choice for families attending Commissioning Week.
-
Commissioning Week dates are in high demand and typically book years in advance. We recommend reserving early to secure your stay.
Still Have Questions?
We’re happy to help with any additional questions as you plan your stay.