10/10 Excellent
Ryan T.
3 January 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place and location
Ryan T.
Stayed 2 nights in Dec 2024
Entire home
Book now for CW 2025 Stay just steps from City Dock at the charming and historic Fleet's Inn
Photo gallery for Book now for CW 2025 Stay just steps from City Dock at the charming and historic Fleet's Inn
Reviews
10 out of 10
Exceptional
2 bedrooms2+ bathroomsSleeps 5
Popular amenities
Explore the area
Annapolis, MD
- Annapolis City Dock2 min walk
- U.S. Naval Academy11 min walk
- Navy-Marine Corps Memorial Stadium3 min drive
- Annapolis, MD (ANP-Lee)21 min drive
Rooms & beds
2 bedrooms (sleeps 5)
Guest Room
2 Single Beds
Primary Bedroom
1 Queen Bed
2 bathrooms, 1 half bathroom
Main Floor Powder Room
Toilet
Second Floor Queen
Bathtub or shower · Toilet
Second Floor Twin
Toilet · Shower only
Spaces
Deck or patio
Kitchen
About this property
Book now for CW 2025 Stay just steps from City Dock at the charming and historic Fleet's Inn
Still available for Commissioning Week 2025!
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
Cozy living room w/ flatscreen TV + folding dining table
Washer/dryer + keyless entry
WiFi + luxury linens + starter toiletries kit
Sleeping Arrangements:2BR / 2.5BA | Sleeps 4 (+1 air mattress + sofa)
Primary Bedroom (2nd Floor): Queen bed, en-suite bath, flatscreen TV
Guest Room (2nd Floor): Two Twin beds, en-suite bath, flatscreen TV
Extras: Air mattress + sofa sleeping (linens on request)
Note: Home has a steep staircase—guests with mobility concerns should inquire before booking.
House Rules:
No pets, smoking, or parties. Renter must be 25+ and present at all times.
Check-in: 4:00 PM | Check-out: 11:00 AM
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
Cozy living room w/ flatscreen TV + folding dining table
Washer/dryer + keyless entry
WiFi + luxury linens + starter toiletries kit
Sleeping Arrangements:2BR / 2.5BA | Sleeps 4 (+1 air mattress + sofa)
Primary Bedroom (2nd Floor): Queen bed, en-suite bath, flatscreen TV
Guest Room (2nd Floor): Two Twin beds, en-suite bath, flatscreen TV
Extras: Air mattress + sofa sleeping (linens on request)
Note: Home has a steep staircase—guests with mobility concerns should inquire before booking.
House Rules:
No pets, smoking, or parties. Renter must be 25+ and present at all times.
Check-in: 4:00 PM | Check-out: 11:00 AM
Property manager
iTrip Vacations Annapolis - Sean Degnan
Premier Host
Languages
English
Add dates for prices
Amenities
Kitchen
Washer
Dryer
Free WiFi
Air conditioning
Outdoor space
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House Rules
Check in after 4:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
No pets allowed
Smoking
Smoking is not permitted
Important information
You need to know
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
About the area
Annapolis
Located in Annapolis, this holiday home is in the city centre. The Colonial Players and Maryland Federation of Art are cultural highlights, and some of the area's attractions include French Soldiers Monument and Annapolis Maritime Museum. Helen Avalynne Tawes Garden and Wild Bird Center are also worth visiting. Jet skiing and kayaking offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking and cycling nearby.
Annapolis, MD
What's nearby
- Annapolis City Dock - 2 min walk - 0.2 km
- William Paca House - 4 min walk - 0.3 km
- Maryland State House - 4 min walk - 0.4 km
- U.S. Naval Academy - 11 min walk - 1.0 km
- Navy-Marine Corps Memorial Stadium - 3 min drive - 2.3 km
Getting around
Restaurants
- The Choptank - 4 min walk
- Starbucks - 3 min walk
- O'Brien's Annapolis' Original Steakhouse - 2 min walk
- Chick & Ruth's Delly - 4 min walk
- Mc Garvey's Saloon - 2 min walk
Frequently asked questions
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window10/10
Cleanliness
10/10
Check-in
10/10
Communication
10/10
Location
10/10
Listing accuracy
Reviews
10/10 Excellent
Jenny H.
15 October 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location
Jenny H.
Stayed 3 nights in Oct 2023
10/10 Excellent
Mike D.
7 October 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Location location and comfortable
Mike D.
Stayed 2 nights in Oct 2024
This review comes from a trusted partner site and has not been verified.
10/10 Excellent
Melissa B.
25 October 2023
Fabulous on Fleet Street
Melissa B.
10/10 Excellent
Kari H.
28 June 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
First timer
Kari H.
Stayed 3 nights in Jun 2024
10/10 Excellent
Amy B., Roswell
16 October 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing!
Amy B.
Stayed 3 nights in Oct 2022
This review comes from a trusted partner site and has not been verified.
10/10 Excellent
john and h.
29 May 2024
Commissioning Week
john and h.
About the host
Hosted by iTrip Vacations Annapolis - Sean Degnan
Languages:
English
Premier Host
They consistently provide great experiences for their guests
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