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

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

A compact kitchen with stainless steel appliances, a small dining area with a round table and chairs, and a nautical-themed rug.
A row of brick buildings with storefronts, a bicycle parked outside, and a sidewalk.
A historic ship docked at a harbor with a prominent white building with a dome in the background.
A living room with a red sofa, a piano, and a rug with 'Navy' written on it. There are framed pictures on the wall and a staircase in the background.
A hotel room with two beds, star-patterned floor, navy-themed wall art, and a central window with patterned curtains.

Reviews

10 out of 10
Exceptional

Entire home

2 bedrooms3 bathroomsSleeps 5950 sq ft

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning
  • Outdoor Space

Explore the area

View in a map
Annapolis, MD
  • Place, Annapolis City Dock
    ‪2 min walk‬
  • Place, Maryland State House
    ‪2 min walk‬
  • Place, U.S. Naval Academy
    ‪3 min walk‬
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪39 min drive‬

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About the neighborhood

Annapolis

Located in Historic District, this vacation home is adjacent to Annapolis City Dock and within a 15-minute walk of popular sights like U.S. Naval Academy. The vacation home includes a kitchen, a patio, and a refrigerator.
View more Vacation Homes in AnnapolisOpens in a new window

What's nearby

  • William Paca House - 2 min walk - 0.1 miles
  • Annapolis City Dock - 2 min walk - 0.1 miles
  • Maryland State House - 2 min walk - 0.1 miles
  • St. John's College - 3 min walk - 0.2 miles
  • U.S. Naval Academy - 3 min walk - 0.2 miles

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
  • ‪The Red Bean - ‬5 min walk
  • ‪Iron Rooster - ‬1 min walk
  • ‪McGarvey's Saloon & Oyster Bar - ‬2 min walk

About this property

Entire place

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

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
The vacation home is air-conditioned and features a kitchen, 2.5 bathrooms, and a patio, and there's space to spread out with 2 bedrooms. Guests can enjoy a TV and stay connected with free WiFi. Other standard amenities include a washing machine, a coffee maker, and an ironing board.

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Property amenities

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

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

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bed sheets 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

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the city center

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)

General

  • Unit size: 950 square feet

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
Information provided by the property may be translated using automated translation tools

Pets

  • This property doesn't allow pets

Children and extra beds

Children allowed: ages 0-17

Events

No events 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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
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
  • Check-in: 4:00 PM
  • Check-out: 11:00 AM
  • Minimum check-in age: 25

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
  • This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.
  • Onsite safety features include a carbon monoxide detector and a smoke detector.

Property is also known as

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

Frequently asked questions

What can I see near this vacation home?

This vacation home is situated in Historic District, just steps from Annapolis City Dock and William Paca House, and within a short walk of Maryland State House. You'll also find The Colonial Players and 97, 99 and 101 East Street less than a mile away.

Is this vacation home associated with a casino?

No, this vacation home is not connected to a casino.

Will I find an indoor pool at this vacation home?

No, there is no indoor pool at this vacation home.

Does this vacation home provide breakfast?

No, this vacation home doesn't offer breakfast.

Will this vacation home allow pets to stay for free?

No, pets aren't allowed at this vacation home.

How close is the airport from this vacation home?

The closest major airport to this vacation home is Fort Meade, MD (FME-Tipton), which is 21.1 mi away (35 minutes by car). Another top airport is Baltimore Washington Intl. Airport (BWI), which is located 29.3 mi away (44-minute drive).

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

Reviews

10

Exceptional

Rating 10 - Excellent. 17 out of 17 reviews
Rating 8 - Good. 0 out of 17 reviews
Rating 6 - Okay. 0 out of 17 reviews
Rating 4 - Poor. 0 out of 17 reviews
Rating 2 - Terrible. 0 out of 17 reviews

10/10

Cleanliness

Reviews

Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
From a partner site

10/10 Excellent

Perfect Location

The place was incredibly comfortable — the kind of comfort that makes you instantly relax the moment you walk in. Everything was clean, thoughtfully arranged, and clearly cared for, which made it feel more like a home than just a stay. The location was absolutely perfect. We could step outside and be moments away from the best of downtown Annapolis — charming shops, waterfront views, historic streets, and great restaurants. Whether I wanted a quiet morning stroll or a lively evening out, everything was right at my fingertips. Overall, it was the ideal spot for enjoying everything Annapolis has to offer. I’d happily stay here again.
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
From a partner site

10/10 Excellent

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 review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
From a partner site

10/10 Excellent

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❤️
From a partner site

10/10 Excellent

Amazing house Amazing Location!

This house was spectacular. The hosts were responsive and super helpful. The house is beautiful decorated and the towels and bedding were top notch. We were in town to drop my son off of Iday at the academy and we literally were only a 5-7 minute walk to the academy. So easy to get there and so close to food, coffee, CVS everything needed was in walking distance.