iTrip in Annapolis, Maryland

“Great location for proximity to everything in Eastport, and just a short walk over the bridge to City Dock and the heart of Annapolis. The home was spotless, tastefully decorated, and recently renovated. The host was responsive and provided clear instructions for check-in and checkout.”

“Charming cottage in a great location! Appreciated the responsive hosts who communicated well! We were checking in late and had some issues getting in and the hosts were prompt in responding despite the hour! They have an electronic guestbook that was very helpful (once I became aware of it). Place was clean, well appointed and maintained!”

“Amazing place with an amazing location. Had some issues with the refrigerator but they came by the next day to fix it”

“This home was right within walking distance on everything we wanted to do downtown. Instructions on how to enter were clear and precise. Cleaning supplies were provided for dishes, laundry, etc. The home has plenty of linens, towels, and blankets for everyone. Overall, a great experience and convenient location for a trip to Annapolis.”

“I booked this property for a work trip, and it stood out immediately for its uniqueness and quality. The home has real character. Being a restored historic firehouse, it feels completely different from a standard rental while still delivering modern comfort and functionality. The multiple living spaces made it easy for our team to spread out without losing that shared, connected feel. The screened porch and balcony ended up being some of the most used areas. They gave us a place to step away and reset without leaving the property. Location in Eastport was also a major advantage with walkable access to restaurants and the waterfront. Sean and Jennifer run a very professional operation. Everything was clear, organized, and consistent with what was advertised. No surprises, just a smooth and well executed stay. If you want something with personality that still performs like a high end, well managed rental, this is a strong choice.”