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Go Navy! Steps to USNA, City Dock & Street Parking

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Go Navy! The Historic Fleet's Inn is just steps to USNA Gate 1 and the Annapolis waterfront.
Go Navy! The Historic Fleet's Inn is just steps to USNA Gate 1 and the Annapolis waterfront
Head through the family room to the kitchen, fully stocked with cookware, plates and glasses.
Sleep on the plush Queen bed in the upstairs en-suite primary bedroom and flatscreen TV
The charming row house is on Historic Fleet Street, less than a block to restaurants, shops and the waterfront.

Reviews

10 out of 10
Exceptional
2 bedrooms2+ bathroomsSleeps 5950 sq ft

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Outdoor space

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

Go Navy! Steps to USNA, City Dock & Street Parking

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

Street Parking available for one car

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

Add dates for prices

Amenities

Kitchen
Washing machine
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
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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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 indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

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. Maryland Hall for Creative Arts and Helen Avalynne Tawes Garden are also worth visiting.
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Map
Annapolis, MD

What's nearby

  • William Paca House - 2 min walk - 0.2 km
  • Annapolis City Dock - 2 min walk - 0.2 km
  • Maryland State House - 2 min walk - 0.2 km
  • U.S. Naval Academy - 3 min walk - 0.3 km
  • Hammond-Harwood House - 5 min walk - 0.4 km

Getting around

  • Odenton Station - 22 min drive
  • Fort Meade, MD (FME-Tipton) - 35 min drive

Restaurants

  • ‪The Choptank - ‬4 min walk
  • ‪Starbucks - ‬2 min walk
  • ‪O'Brien's Oyster Bar & Seafood Tavern - ‬2 min walk
  • ‪Buddy's Crabs & Ribs - ‬2 min walk
  • ‪Annapolis Market House - ‬2 min walk

Frequently asked questions

Is Go Navy! Steps to USNA, City Dock & Street Parking pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Go Navy! Steps to USNA, City Dock & Street Parking?

As of 31 Mar, 2026, prices found for a 1-night stay for 2 adults at Go Navy! Steps to USNA, City Dock & Street Parking on 5 Jul, 2026 start from S$493, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Go Navy! Steps to USNA, City Dock & Street Parking?

On-site parking is available at the property.

What time is check-in at Go Navy! Steps to USNA, City Dock & Street Parking?

Check-in begins at 4:00 PM.

What time is check-out at Go Navy! Steps to USNA, City Dock & Street Parking?

Checkout is at 11:00 AM.

Where is Go Navy! Steps to USNA, City Dock & Street Parking located?

Located in Historic District, this holiday home is within a 15-minute walk of 14 Fleet Street and U.S. Naval Academy. 48 Fleet Street and The Colonial Players are just steps away.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 11 out of 11 reviews
Rating 8 - Good. 0 out of 11 reviews
Rating 6 - Okay. 0 out of 11 reviews
Rating 4 - Poor. 0 out of 11 reviews
Rating 2 - Terrible. 0 out of 11 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Hayden P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had an amazing stay here! Responsive host, amazing location, beautiful home.
Stayed 2 nights in Sep 2025
Response from VrboOwner on 1 Oct, 2025
Thanks, Hayden! We’re thrilled to hear that The Fleet's Inn was amazing for your stay. It’s wonderful to know that you found the location amazing and the home beautiful. We’re glad you enjoyed your time with us and would love to host you again next time you’re in town. Melissa~iTrip Annapolis
Verified

10/10 Excellent

Nancy B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
LOVED the location, close to all of downtown Annapolis and the house was a perfect size for the 4 of us.
Stayed 3 nights in Jul 2025
Response from VrboOwner on 3 Aug, 2025
Thanks, Nancy! We’re thrilled to hear that The Fleet's Inn and its location were perfect for you. Please come back and stay with us again next time you’re here! Meissa~iTrip Annapolis
Verified

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great spot in the middle of everything

A 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!
Stayed 2 nights in Jun 2025
Response from VrboOwner on 22 Jun, 2025
Thank you for staying with us, Seamus & for your positive feedback! We welcome you back anytime! Melissa~iTripAnnapolis
Verified

10/10 Excellent

Jenny H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location

Great accommodations close to the Annapolis Boat Show! Walking distance to all events, restaurants and shopping! Perfect for 2 couples!
Stayed 3 nights in Oct 2023
Response from VrboOwner on 26 Oct, 2023
Thanks, Jenny! Please come back and stay with us again. Sean
Verified

10/10 Excellent

Ryan T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place and location

Would definitely stay again. The parking garage recommended does not open until 6pm to the public on weekends.
Stayed 2 nights in Dec 2024
Response from VrboOwner on 14 Jan, 2025
Hi Ryan! I am very sorry to hear this about your experience with the parking garage, I have never heard of this before & I will make sure to look into why this happened. Thank you for being a great guest! We welcome you back anytime! Melissa~iTripAnnapolis
Verified

10/10 Excellent

Amy B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing!

This property was absolutely beautiful, extremely clean and it was perfect for our girls trip! So close to everything, we would highly recommend it if you come to Annapolis, perfect if you have a kid at the Naval Academy!
Stayed 3 nights in Oct 2022
Response from VrboOwner on 11 Nov, 2022
Thank you Amy! We would love to host you again and we are so happy you enjoyed your stay at The Fleet's Inn! - Cathy
From a partner site

10/10 Excellent

Melissa B.

Fabulous on Fleet Street

This 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!
Verified

10/10 Excellent

Kari H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

First timer

The property was nice and very clean. Easy walk to the Academy.
Stayed 3 nights in Jun 2024
Response from VrboOwner on 6 Jul, 2024
Thank you for staying with us Kari & for your positive feedback! We welcome you back anytime! Melissa~iTripAnnapolis
Verified

10/10 Excellent

Mike D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Location location and comfortable

What 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.
Stayed 2 nights in Oct 2024
Response from VrboOwner on 11 Nov, 2024
Hi Mike! Thank you for allowing us to host your stay & we are thrilled to know you enjoyed your time in the home! We welcome you back anytime, Melissa~iTripAnnapolis
Verified

10/10 Excellent

Courtney T.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This 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!
Stayed 4 nights in Oct 2025
Response from VrboOwner on 21 Oct, 2025
Thanks, Courtney! We’re thrilled to hear that The Fleet's Inn impressed you with its beautiful decor and unbeatable location near the City Dock, USNA, and Main Street. It’s wonderful to know that you found the beds and pillows comfortable and that our management team met your expectations with quick and easy communication. We’re glad you managed to find street parking without too much trouble. We hope to host you again next time you’re in town—just let us know if you need us to save the date for you! Melissa~iTrip Annapolis
From a partner site

10/10 Excellent

john and h.

Commissioning Week

We 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❤️
Response from VrboOwner on 31 May, 2024
Hi Darby- Thank you for your positive feedback & for letting us know you enjoyed your stay! We welcome you back to stay again, anytime! Melissa~iTripAnnapolis

About the host

Hosted by iTrip Vacations Annapolis - Sean Degnan

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Languages:

English

Premier Host

They consistently provide great experiences for their guests
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