See all properties
Entire home

Fleet St Retreat in Downtown - Great Location!

Holiday home with kitchen, near U.S. Naval Academy

Photo gallery for Fleet St Retreat in Downtown - Great Location!

kitchen
Living room
Fleet street- the heart of the action
Main living area
Living area

Reviews

9.6 out of 10
Exceptional
2 bedrooms2+ bathroomsSleeps 5900 sq ft

Popular amenities

  • Dryer
  • Washer
  • Outdoor space
  • Fireplace
  • Kitchen
  • Air conditioning

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)
    ‪32 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 .

Add dates for prices

Amenities

Kitchen
Washing machine
Dryer
Air conditioning
Outdoor space
Fireplace

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Similar properties

Living area
Dean Street's Lower Deck House!
  • Kitchen
  • Washer
  • Dryer
  • Pet-friendly
10.0 out of 10, (2 reviews)
Dean Street's Lower Deck House!

House Rules

Check in after 3:00 PM
Minimum age to rent: 18
Check out before 10:00 AM
default

Children

Children allowed: ages 0–17
default

Events

No events allowed
default

Pets

No pets allowed
default

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
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
  • U.S. Naval Academy - 3 min walk - 0.3 km
  • Thurgood Marshall Memorial - 3 min walk - 0.3 km

Getting around

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

Restaurants

  • ‪O'Brien's Oyster Bar & Seafood Tavern - ‬3 min walk
  • ‪Starbucks - ‬3 min walk
  • ‪Annapolis Market House - ‬3 min walk
  • ‪McGarvey's Saloon & Oyster Bar - ‬2 min walk
  • ‪Chick & Ruth's Delly - ‬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 within a 15-minute walk of 48 Fleet Street and U.S. Naval Academy. The Colonial Players and 97, 99 and 101 East Street are just steps away.

Reviews

9.6

Exceptional

9.6/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

9.8/10

Listing accuracy
Rating 10 - Excellent. 53 out of 62 reviews
Rating 8 - Good. 6 out of 62 reviews
Rating 6 - Okay. 2 out of 62 reviews
Rating 4 - Poor. 1 out of 62 reviews
Rating 2 - Terrible. 0 out of 62 reviews

Reviews

8/10 Good

Tracey R.

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

10/10 Excellent

Chris L.

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

10/10 Excellent

charles c.

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

10/10 Excellent

Tracie H.

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

10/10 Excellent

Rosina S.

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

10/10 Excellent

Tina A.

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

10/10 Excellent

Wendy

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

10/10 Excellent

Carolyn W.

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

10/10 Excellent

Ashley J.

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

Perfect Location

We had a wonderful stay for a wedding weekend in Annapolis. Worked really well for 2 couples and was so close to Gate 1. We parked our car and didn’t need it for the rest of the weekend. We had excellent communication with M and really appreciated the early check-in.
Stayed 2 nights in Apr 2025

10/10 Excellent

Kim B.

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

Great location

We enjoyed our stay on
Stayed 3 nights in Oct 2023

10/10 Excellent

Heather M.

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

10/10 Excellent

Kristi S.

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

Birthday trip

Stopped in to see my mid for his birthday. The spot on fleet st is wonderful. Convenient location, exactly as pictured, well stocked with what you need. Would love to rent again.
Stayed 3 nights in Feb 2025

10/10 Excellent

Elizabeth C.

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

There for a wedding

We did not spend much time in the cute town house but it was clean and comfortable. The only issue was not understanding the door lock and finding the door open when we returned from an extended event.
Stayed 3 nights in May 2025

10/10 Excellent

Jason G.

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

10/10 Excellent

Carissa N.

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

10/10 Excellent

Leslie H.

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

8/10 Good

Cathy S.

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

Excellent Location

This property is in a perfect location, can walk everywhere. The bedrooms were perfect for the two adult couples staying, one queen and one king. Be aware the queen is up against the wall, so makes getting out during the night a bit of a challenge. Megan was lovely to deal with, but also no there is no wiggle room on early check in or late check out. Overall we enjoyed our stay
Stayed 2 nights in Feb 2025

10/10 Excellent

Penny S.

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

10/10 Excellent

Lori A.

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

Fantastic Location

We stayed at this property for the USNA Halloween Concert. The house had everything you need and both bedrooms were spacious and comfortable. The location is perfect with the ability to walk to anything downtown and the Yard. The extra built-in bunk was really useful for extra sleeping. The host was particularly helpful and accommodating! We would definitely stay there again.
Stayed 3 nights in Oct 2024

8/10 Good

Jessica W.

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

10/10 Excellent

Jonathan T.

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

Very convenient!

The property met all of our needs and was located perfectly, allowing for short walks to any-and-everywhere we wanted to go.
Stayed 3 nights in Jan 2023

10/10 Excellent

Scott S.

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

Great Location!

We had a great visit to Annapolis and this place put us right in the middle of all of the great things to see. Megan was easy to communicate with…and really just no complaints. Thanks!
Stayed 2 nights in Mar 2023

10/10 Excellent

Kathy S.

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

Great vacation

Property was clean, comfortable, and very well stocked. Walking distance to restaurants, bars, and shopping. 45 min drive to DC. Spent the day exploring DC then relaxing here, walking around time, explored this beautiful city. Would definitely come back for next DC trip.
Stayed 3 nights in Sep 2023

10/10 Excellent

Morgan M.

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

Beautiful decor, great location. Thank You

Fantastic! Very comfortable. Plenty of space. Loved the nautical theme. Great communication.
Stayed 3 nights in Oct 2021

10/10 Excellent

Verified traveller

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

Plebe Parent Weekend

This property was perfect for our family. The home came complete with everything we could possibly need and it was so comfortable and felt like home for our 3-day visit. It was a short walk to the visitors gate at USNA as well as great restaurants and shops. The property manager was wonderful answering any questions we had.
Stayed 4 nights in Aug 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
Tell us how we can improve our siteShare feedback

Hotels

Holiday Rentals