Go Navy! Steps to USNA, City Dock & Street Parking
Annapolis, Maryland
2
Bed
2
Bath
Private Vacation Home
Property Type
5
Max Sleeps
2 nights
Min Stay
Experience the Difference: Professionally Managed by iTrip Annapolis
Stay in the heart of Historic Annapolis just steps from the waterfront, shops, restaurants, and the Naval Academy. Owned by a proud multi-generational Navy family, this charming updated home blends modern comfort with patriotic décor.
Highlights:
1 block to City Dock & USNA
Private brick patio w/ grill & outdoor dining
Fully-equipped gourmet kitchen
Stree
Features
Map
Availability
Review
Features
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PETS
No Pets Allowed -
DINING
Dining Table -
SAFETY
Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property) -
BEDROOM
2 Bedrooms Bed Sheets Provided -
GENERAL
Unit Size: 950 Sq Ft (88 Sq M) -
KITCHEN
Coffee/tea Maker Dishwasher Ice Maker Microwave Oven Paper Towels Refrigerator Stovetop Toaster -
LAUNDRY
Laundry Facilities Washing Machine And Dryer -
PARKING
Onsite Parking -
INTERNET
Free WiFi -
OUTDOORS
Barbecue Grill Outdoor Furniture Patio -
BATHROOMS
2.5 Bathrooms Bathtub Or Shower Hair Dryer Shampoo Soap Toilet Paper Towels Provided -
LANGS SPOKEN
English -
ENTERTAINMENT
TV -
LIVING SPACES
Living Room -
CLIMATE CONTROL
Air Conditioning Heating -
FAMILY FRIENDLY
Children's Games -
LOCATION HIGHLIGHTS
In The City Center -
SERVICES AND CONVENIENCES
Iron/ironing Board -
SUITABILITY/ACCESSIBILITY
Smoke-free Property
Check-in : 04:00 PM
Check-out : 11:00 AM
No Wheelchair
No smoking
No pets
Children allowed
Max occupancy : 5
Map
Availability
Review
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Courtney T.
Submitted Oct 17, 2025
Stayed Oct 9, 2025This is a beautiful, well-decorated home in an unbeatable location—just steps from the City Dock, USNA, and Main Street. The house was very comfortable, and everyone raved about the beds and pillows! The management team was a pleasure to work with—super easy to reach by text and always quick to respond.Parking in downtown Annapolis can be tricky, but we were always able to find street parking nearby without too much trouble. I would absolutely stay here again and recommend it to friends and family—unless, of course, they’re planning to visit the same weekend we are… in that case, I’d definitely not recommend it!
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Hayden P.
Submitted Sep 30, 2025
Stayed Sep 26, 2025We had an amazing stay here! Responsive host, amazing location, beautiful home.
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Nancy B.
Submitted Jul 26, 2025
Stayed Jul 23, 2025LOVED the location, close to all of downtown Annapolis and the house was a perfect size for the 4 of us.
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Submitted Jun 20, 2025
Stayed Jun 13, 2025A perfect place to stay for a weekend in Annapolis…walking distance to everything, and the house is really comfortable and nicely appointed. Would stay here again for sure!
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Ryan T.
Submitted Jan 3, 2025
Stayed Dec 27, 2024Would definitely stay again. The parking garage recommended does not open until 6pm to the public on weekends.
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Mike D.
Submitted Oct 7, 2024
Stayed Oct 4, 2024What a great little place to stay. The location is in the heart everything but off on a side street. So cozy and comfortable with everything updated. The decor is another awesome feature to this home. We will be back again and hope that this home is available.
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Kari H.
Submitted Jun 28, 2024
Stayed Jun 25, 2024The property was nice and very clean. Easy walk to the Academy.
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john and h.
Submitted May 29, 2024
Stayed Dec 31, 1969We had the absolute best week. We've stayed in Kevin's place before and love the location and home. We got in late Saturday and had a question, iTrip responded immediately. We had a small issue with AC as it was probably the first warmer days so far, and it was corrected immediately. The Fleet Street location, owners, and iTrip Annapolis were all fabulous! We've stayed all over the area for past 10 years but it is my favorite place by far❤️
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Melissa B.
Submitted Oct 25, 2023
Stayed Dec 31, 1969This is a wonderful, fully equipped house close to everything in DTA. There was plenty of room, and it was extremely clean. Will definitely stay here again!
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Jenny H.
Submitted Oct 15, 2023
Stayed Oct 12, 2023Great accommodations close to the Annapolis Boat Show! Walking distance to all events, restaurants and shopping! Perfect for 2 couples!
