Entire home

Available for CW 2025 Stay just steps from City Dock in the Historic Fleet's Inn

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Welcome to The Historic Fleet's Inn just steps to USNA Gate 1 and the Annapolis waterfront!
Soak in the sunshine in the private fenced-in back patio has with a grill and seating for 4.
The charming row house is on Historic Fleet Street, less than a block to restaurants, shops and the waterfront.
Sleep on the plush Queen bed in the upstairs en-suite primary bedroom.
Watch the Blue Angels from the back patio.

Reviews

10 out of 10
Exceptional
2 bedrooms2+ bathroomsSleeps 5

Popular amenities

  • Barbecue grill
  • Washer
  • Dryer
  • Kitchen
  • Outdoor space
  • Free WiFi

Explore the area

Map
Annapolis, MD
  • Annapolis City Dock
    ‪2 min walk‬
  • U.S. Naval Academy
    ‪11 min walk‬
  • Navy-Marine Corps Memorial Stadium
    ‪3 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

Available for CW 2025 Stay just steps from City Dock in the Historic Fleet's Inn

Still available for Commissioning Week 2025!

Stay just steps from the Annapolis waterfront! Cherished by the multi-generational Navy owners who have updated the modern home, while maintaining the charm of residing on the Historic District's Fleet Street. Enter the sunny family room decorated in full Semper Fi pageantry. Head back to the gourmet kitchen, with sleek granite counter tops, stainless steel appliances and all of the kitchen tools you'll need for your stay. Head out to the private fenced stone patio where you'll find a BBQ grill and seating for 4 under the umbrella at the table. In the hall of the main floor you'll find the powder room and full laundry room.

Head up the Navy-decorated stairway to the 2 bedrooms and 2 full baths on the second floor. The en-suite primary Bedroom has a Queen bed, flatscreen TV and a shower/tub combo. Across the hall is the guest bedroom with 2 twin beds and an en-suite full bath with stand-up shower.

When you are ready to see the sights of Annapolis, step outside on to the cobblestone street just one block to the City Dock, shops, restaurants and the Naval Academy.

SLEEPING ARRANGEMENTS 2 BR / 2.5 BA / Sleeps 4 (plus 1 more on an air mattress and additional sleeping on main floor sofa - both with linens available upon request):
Primary Bedroom:
- Second Floor
- Queen Bed
- Flatscreen TV
- En-Suite full bath

Twin Guest room:
- Second Floor
- Two Twin Beds
- Twin air mattress with linens
- Flatscreen TV
- Full en-suite bath

HIGHLIGHTS:
- Full gourmet kitchen with stainless steel appliances and granite countertops
- Private back brick patio with outdoor dining table for 4
- Eat-in kitchen table seats 2
- Seating for 4 at the folding table that pops up in the living
- BBQ Grill with a tank
- WiFi
- Multiple flatscreen TV's
- Luxury linens, complimentary toiletries Starter Kit, and boutique-level service
- Washer & dryer located inside the home
- Elderly and guests with mobility issues may want to inquire about the steep staircase and/or may want to consider other accommodations.
- Keyless entry. Drive straight to your rental home and enter the electronic lock code on the front door.

Property Distance to:
- U.S. Naval Academy – 1 block
- Washington, DC – 30 miles
- Baltimore - 25 miles

*Amenity & Supplies starter pack, coffees and sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid.
* All beds are ready made for you with freshly laundered sheets & towels.

House Rules
Reservations made for teenagers or young single groups will not be honored without any accompanying adult staying in the unit at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No smoking/no pets. Please respect the neighbors and neighborhood. No parties, events or smoking of any kind.
Check-in time: 4:00 pm
Check-out time: 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
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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 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.
Map
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

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

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

Is Available for CW 2025 Stay just steps from City Dock in the Historic Fleet's Inn pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Available for CW 2025 Stay just steps from City Dock in the Historic Fleet's Inn?

Check-in begins at 4:00 PM.

What time is check-out at Available for CW 2025 Stay just steps from City Dock in the Historic Fleet's Inn?

Checkout is at 11:00 AM.

Where is Available for CW 2025 Stay just steps from City Dock in the Historic Fleet's Inn 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. 7 out of 7 reviews
Rating 8 - Good. 0 out of 7 reviews
Rating 6 - Okay. 0 out of 7 reviews
Rating 4 - Poor. 0 out of 7 reviews
Rating 2 - Terrible. 0 out of 7 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

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

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

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
This review comes from a trusted partner site and has not been verified.

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!

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

10/10 Excellent

Amy B., Roswell

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
This review comes from a trusted partner site and has not been verified.

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❤️

About the host

Hosted by iTrip Vacations Annapolis - Sean Degnan

Host profile image

Languages:

English

Premier Host

They consistently provide great experiences for their guests