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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

Exterior
2 bedrooms, iron/ironing board, free WiFi, bed sheets
TV
Fridge, microwave, oven, stovetop
TV

Reviews

10 out of 10
Exceptional

Entire home

2 bedrooms3 bathroomsSleeps 4

Popular amenities

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

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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

Property manager

iTrip Vacations Annapolis - Sean Degnan

Languages

English

Add dates for prices

Property amenities

Internet

  • Available in the house: Free WiFi

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Ice maker
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 2.5 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

  • TV

Outdoor areas

  • Barbecue grill
  • Outdoor furniture
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the city center
  • Near a health/beauty spa
  • Near a hospital
  • Near the bay
  • Near the marina

Things to do

  • Cycling nearby
  • Fishing nearby
  • Golfing nearby
  • Hiking/biking trails nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Sailing nearby
  • Swimming nearby
  • Water skiing nearby
  • Water tubing nearby

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector not reported (host has not indicated whether there is a smoke detector on the property)

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Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age: 25

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

Pets not allowed

Children and extra beds

Children are welcome

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
Onsite 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
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

Property is also known as

30 Fleet Street Annapolis
8361
30 Fleet Street Private vacation home
30 Fleet Street Private vacation home Annapolis

About the neighborhood

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?

Check-out 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 vacation 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.

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Book now for CW 2025 Stay just steps from City Dock at the charming and historic Fleet's Inn Reviews

Reviews

10

Exceptional

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

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❤️