Entire home

Fleet St Retreat in Downtown - Great Location!

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A kitchen with a bar area, wooden stools, a dolphin wall decoration, and a nautical-themed rug.
A modern interior with a staircase, a dining area with a table and chairs, and a living room with a sofa and a coffee table.
A bedroom with a bed, a ceiling fan, and a window with blinds.
A living room with a blue sofa, a grey sofa, a wooden coffee table, and nautical-themed pillows.
A marina with boats docked, a flagpole with an American flag, and a statue of a person.

Reviews

9.6 out of 10, Loved by Guests
Top 10% of guest reviews in this area
With space for 5 guests, this vacation home features 2 bedrooms and 2 bathrooms. It includes a patio for outdoor enjoyment. Attractions such as 97, 99, and 101 East Street, along with 48 Fleet Street, provide diverse options for exploration.

Highlights

  • Family fun awaits
    Top-rated for families.
  • At the centre of it all
    Stay in a top rated central location, steps from the best attractions, dining, and entertainment.
  • Discover nearby landmarks
    Near Maryland State House
2 bedrooms2+ bathroomsSleeps 5

Popular amenities

  • Kitchen
  • Washing machine
  • Air-conditioning
  • Deck or patio
  • Internet access
  • Fireplace

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)
    ‪37 min drive‬

Rooms & beds

2 bedrooms (sleeps 5)

Bedroom 2

1 Single Bed and 1 King Bed

Master

1 Queen Bed

2 bathrooms, 1 half bathroom

First floor

Master

Second Full

Spaces

Deck or patio
Kitchen
Garden

About this property

Fleet St Retreat in Downtown - Great Location!

We welcome you to our renovation on historic Fleet Street. Purchased in 2016 this house was taken down to the studs so everything is brand new and waiting to host you on your next trip to Annapolis. Literally a stones throw from everything downtown has to offer you can’t get closer to the action. USNA, Maryland State House, City Dock, McGarveys and Iron Rooster are just around the corner. Perfect place for two couples and a extra single. Small city patio out back.

We are in the heart of downtown Annapolis. Guests have the full townhouse to themselves

There is no parking at this location - guests use one of the city garages all Located within a few block walk

Quiet Hours after 9pm. No parties ( Bach / ette included ) No pets or smoking.

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House Rules

Check in after 3:00 PM
Minimum age to rent: 24
Check out before 10:00 AM
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Children

Adults only
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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

Property # 1825982vb
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
Safety features at this property include a fire extinguisher and a first aid kit

About the area

Annapolis

Historic District, a neighbourhood in Annapolis, is home to this holiday home. The Colonial Players and Maryland Federation of Art are cultural highlights, and some of the area's landmarks include 14 Fleet Street and Kunta Kinte Plaque & Alex Haley Memorial. French Soldiers Monument and Annapolis Maritime Museum are also worth visiting.
View more Holiday homes in AnnapolisOpens in a new window
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
  • St. John's College - 3 min walk - 0.3 km
  • U.S. Naval Academy - 3 min walk - 0.3 km

Getting around

  • Odenton Station - 29 min drive
  • Fort Meade, MD (FME-Tipton) - 30 min drive

Restaurants

  • ‪The Choptank - ‬4 min walk
  • ‪Starbucks - ‬3 min walk
  • ‪The Red Bean - ‬4 min walk
  • ‪McGarvey's Saloon & Oyster Bar - ‬2 min walk
  • ‪Middleton Tavern - ‬3 min walk

Frequently asked questions

Is Fleet St Retreat in Downtown - Great Location! pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Fleet St Retreat in Downtown - Great Location!?

Check-in begins at 3:00 PM.

What time is check-out at Fleet St Retreat in Downtown - Great Location!?

Checkout is at 10:00 AM.

Where is Fleet St Retreat in Downtown - Great Location! located?

Located in Historic District, this holiday home is steps away from 48 Fleet Street and Annapolis City Dock. The Colonial Players and 97, 99 and 101 East Street are just steps away.

Reviews

9.6

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 62 out of 73 reviews
Rating 8 - Good. 8 out of 73 reviews
Rating 6 - Okay. 2 out of 73 reviews
Rating 4 - Poor. 1 out of 73 reviews
Rating 2 - Terrible. 0 out of 73 reviews

9.6/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

9.8/10

Listing accuracy

Reviews

Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location
Stayed 2 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location—very convenient to the waterfront, shops, restaurants and the Naval Academy.
Stayed 3 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
It was a great stay. Everything was clean, safe and comfortable. The location could not have been better. Highly recommend.
Stayed 4 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Our host was great about communicating and the property was perfect for our weekend in Annapolis. Centrally located. Easy to walk to restaurants and shops.
Stayed 2 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a wonderful stay at Megan’s property. It was conveniently located in the heart of lovely downtown Annapolis. The property was spacious and clean. There is even a small area across the street from the property with 4 park benches and beautiful old trees to sit & relax & enjoy a cup of coffee. In addition, the property owner was so accommodating when I realized that I left a closetful of jackets in the downstairs closet. She brought them to a local UPS store so that I could have them shipped home to me! You can’t beat that type of service! If you decide to go, enjoy your stay.
Stayed 2 nights in Sep 2026
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great Stay, Great location!
Stayed 3 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location to downtown Annapolis! Very clean. Showing some wear, but not inconsistent with a rental that probably gets a lot of use. Would stay here again.
Stayed 2 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
Very clean and comfortable…. Close to everything downtown
Stayed 3 nights in Feb 2026
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Homie, clean, and super close to all the things we love about DTA.
Stayed 3 nights in Feb 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This property was perfect for our family of 4 -- plenty of space and well-appointed kitchen. Literally in the middle of the action -- we walked everywhere except when we took the 45 minute drive to the National Aquarium in Baltimore. We enjoyed several good restaurants and ice cream shops in Annapolis, and took the short harbor cruise to get a better look at the Naval Academy! Hosts were responsive and helpful :) 10/10
Stayed 3 nights in Apr 2026
Verified review

10/10 Excellent

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

Great location

We enjoyed our stay on
Stayed 3 nights in Oct 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Awesome stay, great location, super comfy!! THX!
Stayed 2 nights in Sep 2025
Verified review

10/10 Excellent

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

Comfortable and ideally located

We had a terrific stay. The home is central to everything Annapolis and nicely decorated.
Stayed 2 nights in Mar 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Location was amazing and the bedrooms very comfortable. Overall very clean and well maintained. Also appreciated how well stocked it was (I.e. coffee filters, dish soap, shampoo, hair appliances, linens, etc).
Stayed 2 nights in Oct 2025
Verified review

10/10 Excellent

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

Adorable perfectly located home downtown Annapolis

This place is perfectly located in downtown Annapolis. We loved the location and the house is adorable.
Stayed 2 nights in Apr 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
All was good
Stayed 2 nights in Dec 2025
Verified review

10/10 Excellent

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

Great spot and house

This is the best place we’ve ever stayed in DTA! House is so comfortable and close to everything. We will definitely stay again!
Stayed 2 nights in Jun 2023
Verified review

10/10 Excellent

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

Great place in the middle of everything!

Thank you! We had a great stay. We will stay here again soon!
Stayed 3 nights in Mar 2024
Verified review

10/10 Excellent

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

Location is amazing

This property has a fabulous location so near to restaurants, shopping and Naval Academy. It’s been nicely modernized but still maintains the quaintness that is Annapolis. The property owners are easy to contact and quick to respond.
Stayed 4 nights in Jun 2025
Verified review

10/10 Excellent

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

Quick trip to visit our Mid

This was a perfect place to stay for a visit with our mid during a very busy time. We came in the weekend before graduation to have a few days with our son and it was a great size and location. Would rebook for sure!
Stayed 4 nights in May 2025
Verified review

10/10 Excellent

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

Couples weekend

A cute home, great location. The place was clean and comfortable.both bedrooms have there own bath which is important for 2 couples. The patio in the back needs some TLC.
Stayed 3 nights in Jul 2025
Verified review

10/10 Excellent

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

Location!

We so enjoyed our stay in Annapolis. The home was the perfect place to enjoy the charm and history of the town. Thank you for sharing this comfy, well-appointed space!
Stayed 2 nights in Jul 2023
Verified review

10/10 Excellent

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

Great location and property!

We had a great stay at this property. The house was very clean and the owner was very responsive to our questions. The location was great as well! It was within walking distance to various restaurants and local sites, and parking in the garages was very easy. We would be happy to stay here again!
Stayed 2 nights in Feb 2024
Verified review

10/10 Excellent

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

Great location

Loved the house!! Inside was decorated beautifully. Beds were comfortable. The outside needs a good painting and needs a new door. Overall a wonderful house!
Stayed 2 nights in May 2025
Verified review

8/10 Good

Liked: Check-in, communication, location, listing accuracy

Amazing Location, Easy Stay

Our group of five friends enjoyed the amazing location to shop, dine and enjoy downtown Annapolis. The house could use a paint refresher and a long mirror to ease getting ready.
Stayed 2 nights in Jun 2023

About the host

Hosted by M

Host profile image
Megan is a local owner and property manager of Short term rentals in the Annapolis area any beyond . Born and raised in Downtown Annapolis she is your go to person for all things local . Reach out with any questions - we’d love to help you plan your next trip !

Why they chose this property

This was a old rowhouse on Fleet that had to be taken down to the studs . We are super proud of our renovation job and know you will be too !

What makes this property unique

Heart of Downtown . Walk to city dock , USNA , all Churches , AYC in just a few minutes . Parking will need to be in one of our numerous local garages as the city no longer allows parking passes to short term rentals .

Premier Host

They consistently provide great experiences for their guests
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