Entire home

Historic Downtown Charmer, Water Views and Parking!

Holiday home with kitchen, 3-minute walk to U.S. Naval Academy

Photo gallery for Historic Downtown Charmer, Water Views and Parking!

Living Room with Fireplace
Living Room
Living Room with Cable Television
Dining
Queen Master

Reviews

10 out of 10
Exceptional
2 bedrooms1+ bathroomSleeps 5

Popular amenities

  • Washer
  • Dryer
  • Kitchen
  • Outdoor space

Explore the area

View map
  • Place, Annapolis City Dock
  • Place, U.S. Naval Academy
  • Place, Navy-Marine Corps Memorial Stadium
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)

Rooms & beds

2 bedrooms (sleeps 5)

Bedroom 1

1 Queen Bed

Bedroom 2

2 Single Beds

1 bathroom, 1 half bathroom

Bathroom 1

Bathtub or shower · Toilet

Bathroom 2

Toilet

Spaces

Deck or patio
Kitchen
Balcony
Dining area

About this property

Historic Downtown Charmer, Water Views and Parking!

Life is beautiful in historic downtown Annapolis, with great restaurants, shops and romantic waterfront at your doorstep. Live like a local in a home built in 1875 but updated for today's lifestyles. This two bedroom, 1 1/2 bath home with a designated, off-street parking space -- a rare perk in this National Landmark district -- makes it easy for guests to arrive, unpack and unplug.

Walk down Pinkney Street to experience the restaurants and shops of downtown and see the yachts along Ego Alley. Visit the United States Naval Academy just three blocks away. Or walk up the street on brick and cobblestone sidewalks to explore the grounds of the oldest state house in continued use in America or St. John's College, dating to the 17th century. Experience the restaurants, charming antique stores and neighborhoods around State and Church Circles and beyond.

This 1875 cedar shake home sits in a row of townhouses that have been updated for modern living, with hardwood floors and ceramic tile on the main floor and new carpeting in the bedrooms. Enjoy the cozy fireplace during the cold winter nights, or in the warm summer months, take your morning coffee or afternoon cocktails to the rooftop deck to enjoy views of the water, the boats and City Dock.

This well-decorated house features an open floor plan with updated, fully equipped kitchen, a living room with flat-screen TV and fireplace, dining room and half bath on the first level. There is a small deck facing the courtyard and parking with space to sit and enjoy the morning sun. On the second floor, the generously sized queen bedroom features a walk-in closet, private access to a shared bath and wall-mounted flat screen television. A well-appointed guest room provides two comfortable twin beds. But the second floor also contains a hidden surprise -- a skylit ship's ladder to a widow's walk and rooftop deck with beautiful views of Ego Alley and Spa Creek.

As with any luxury property, the essentials -- linens, WiFi, coffee, and toiletries -- are included.

Historic Annapolis is the place to be during Naval Academy events and football games, St. John's College visits and graduation, boat shows and more. It is the perfect destination for a romantic weekend, a girls' getaway, family reunions, temporary military assignment and more. Consider making this cozy retreat on a historic street your home away from home when you come to visit Maryland's state capital.

Add dates for prices

Amenities

Kitchen
Washing machine
Dryer
Air conditioning
Outdoor space
Water view

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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 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 deadlock
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

We should mention

A car is not required for transport to and from this property

About the area

Annapolis

Located in Annapolis, this holiday home is in the city centre. Annapolis Harbor and Ego Alley are worth checking out if an activity is on the agenda, while those in the mood for shopping can visit Annapolis City Dock and Bay Bridge Market Place Shopping Center. French Soldiers Monument and Annapolis Maritime Museum are also worth visiting. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
Annapolis, MD

What's nearby

  • Annapolis City Dock - 1 min walk - 0.0 km
  • U.S. Naval Academy - 2 min walk - 0.2 km
  • Maryland State House - 3 min walk - 0.3 km
  • Annapolis Maritime Museum - 19 min walk - 1.6 km
  • Navy-Marine Corps Memorial Stadium - 3 min drive - 2.5 km

Getting around

  • Odenton Station - 29 min drive
  • Fort Meade, MD (FME-Tipton) - 25 min drive

Restaurants

  • ‪The Choptank - ‬3 min walk
  • ‪O'Brien's Oyster Bar & Seafood Tavern - ‬3 min walk
  • ‪Starbucks - ‬2 min walk
  • ‪Annapolis Market House - ‬1 min walk
  • ‪McGarvey's Saloon & Oyster Bar - ‬1 min walk

Frequently asked questions

Is Historic Downtown Charmer, Water Views and Parking! pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Historic Downtown Charmer, Water Views and Parking!?

Check-in begins at 4:00 PM.

What time is check-out at Historic Downtown Charmer, Water Views and Parking!?

Checkout is at 11:00 AM.

Where is Historic Downtown Charmer, Water Views and Parking! located?

Located in Historic District, this holiday home is within a 5-minute walk of Annapolis City Dock and U.S. Naval Academy. 14 Fleet Street and Kunta Kinte Plaque & Alex Haley Memorial are just steps away.

Reviews

10

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. 123 out of 130 reviews
Rating 8 - Good. 7 out of 130 reviews
Rating 6 - Okay. 0 out of 130 reviews
Rating 4 - Poor. 0 out of 130 reviews
Rating 2 - Terrible. 0 out of 130 reviews

9.8/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Angela S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location and very nice place. Owner was very friendly and responsive.
Stayed 3 nights in Sep 2025

8/10 Good

John M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location for all Naval Academy activities!! Patricia's instructions were clear and very helpful and she was very accommodating on check-in time.
Stayed 3 nights in Oct 2025

10/10 Excellent

Susan C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Nice comfortable stay and perfect location. Had a lovely chat with the owner when we couldn’t figure out the thermostat. She was able to remotely reset it from cool to heat. Highly recommend.
Stayed 2 nights in Oct 2025

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent location, walking distance to the Naval Academy, beautiful home and owner was super easy to work with. We would definitely book again!
Stayed 7 nights in May 2025

10/10 Excellent

ana c.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very easy to check in. Very clean and cozy. The owner’s communication was great. But the biggest perk to this place was the parking spot for it and the location. One block away from the academy, restaurants, shopping. All the necessary amenities in the house also.
Stayed 4 nights in Sep 2025

10/10 Excellent

Philip B.

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

Great place in a great location

Good communication, perfect location and a parking space was a real bonus.
Stayed 2 nights in Oct 2024

10/10 Excellent

Michelle W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
I wish I could leave more than 5 stars. Patty the property owner was incredible to correspond with. The house location was amazing. You are close to absolutely everything and there are two coffee shops right within a block of the home. The house was very nicely appointed and perfect for a family of four. We can't wait to book again and look forward to many more stays at this wonderful home.
Stayed 3 nights in Jul 2025

10/10 Excellent

Sandra W.

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

Lovely comfortable house

Very nice location. Very comfortable and clean. I would stay again.
Stayed 17 nights in Dec 2024

10/10 Excellent

Lewis H.

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

Visiting home town

The location can’t be beat.
Stayed 8 nights in Jul 2024

10/10 Excellent

Erin S.

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

Great stay in Annapolis

I would give more stars for the location if I could. On a pretty quiet street right in the middle of everything. The unit was great and was exactly as described.
Stayed 3 nights in Nov 2024

10/10 Excellent

Kristen S.

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

Perfect location for girls getaway!

The home was such a great home base for our reunion in Annapolis. The owner was so friendly and accommodating. Great food and drink recommendations. The location is unbeatable and everything was clean and comfortable. The shower head and water pressure were also worth noting. We would love to stay at 19 Pinkney again!
Stayed 2 nights in Jun 2024

10/10 Excellent

David S.

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

Old Town Annapolis

Comfortable and very well maintained townhouse with off-street parking in downtown Annapolis. Walking distance to Naval Academy, Annapolis Harbor, Church and State Circles, and Market Street. Outstanding choice of restaurants. Ideal summer getaway.
Stayed 4 nights in Aug 2023

10/10 Excellent

Stephen C.

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

Great Location and Dedicated Parking

We enjoyed our weeklong stay at this wonderful location. The location is ideal for getting to local restaurants and the Academy. A dedicated parking spot behind the gates allowed us to unpack for our stay and easily run out for day trips without worrying about finding a parking spot - especially during the weekends and when the downtown parade was occurring. Thanks for the great stay!
Stayed 8 nights in Jun 2023

10/10 Excellent

Nick B.

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

Location and Parking!

Your in the center of it all with a parking spot! Was literally in the middle of historic tour, many spots were across or next to the house.
Stayed 2 nights in Jul 2023

10/10 Excellent

Charles S.

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

A Little Business at USNA

The property was charming, wonderfully convenient to both the Academy and downtown, and well-equipped. The included parking space insured a five star rating! I hope to stay again and take advantage of the rooftop view and a nice glass of wine at sunset.
Stayed 2 nights in Oct 2023

10/10 Excellent

Dan K., Middletown, USA

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

Wonderful Stay in Annapolis!

We thoroughly enjoyed our stay and really couldn't have asked for more. Perfect location, right in the middle of everything, but still private enough to be a little oasis. The roof top deck was great and we enjoyed ending our day up there with a glass of wine. Having parking was a big plus and it was nice to be able to park and just leave the car until we were ready to leave. We were sad to go and plan to come back for a visit soon. Thanks for a great trip!
Stayed 2 nights in May 2023

10/10 Excellent

Erin L.

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

Reconnect Weekend

Came to Annapolis to meet some old friends! It is a perfect location to downtown, the docs and The Choptank. Simple walk to the Naval Academy and St John’s. The place was great. Nice layout and the rooftop deck was amazing. Having a place to park is a huge plus. Would definitely make this my choice for all Annapolis visits!
Stayed 2 nights in Jun 2023

8/10 Good

Barry S.

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

Winter weekend

Our host was very accommodating, allowing for early checkin and delayed departure since the unit was not in use. The location is perfect for access to the heart of the shops and restaurants in Annapolis. We could roll out of bed and into the Iron Rooster for breakfast. The heating unit was a little noisy in the main bedroom, so we switched to the 2nd bedroom for a quiet night's sleep. That shouldn't be a problem in the other seasons when the heat isn't needed.
Stayed 2 nights in Jan 2022

10/10 Excellent

Deb T.

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

Long weekend in Annapolis

This is a great little townhouse right downtown Annapolis. We had a little problem getting in but it looks just like the pictures. Very comfortable, a perfect size. A block to all the restaurants and stores downtown. It is even an easy walk across the bridge to the restaurants south of downtown and it's three blocks to the Naval Academy entrance. Because you are so close to several of the more popular restaurants /bars, it was noisy in the front bedroom Friday night (could be because it was Labor Day weekend or a Navy football weekend). The back bedroom was quiet. FYI, the parking in back is a little tight if you have a large car, but it's nice to have it. The kitchen is nicely stocked and we could have easily stayed in and cooked if we wanted to. Thank you for having us and our pups. We had a great weekend.

10/10 Excellent

lovada a.

Liked: Check-in, communication, location, listing accuracy
Carpeting on the second floor is in desperate need of cleaning or replacing. Not healthy.
Stayed 4 nights in Sep 2025

10/10 Excellent

Theresa R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent location! Owner is very responsive and helpful
Stayed 2 nights in Aug 2025

10/10 Excellent

Lorraine K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We enjoyed staying in the Historic Dowtown charmer. We walked everywhere. It was great having a parking space for the car. We would stay again. Property match all the photos that are on the website. No hidden surprises. Place was clean and we had everything we needed for a long weekend visit. Property owners are a pleasure to work with.
Stayed 3 nights in Aug 2025

10/10 Excellent

Paul H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovely Annapolis home in a great location
Stayed 2 nights in Aug 2025

10/10 Excellent

Tom M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place in DTA - perfect location for walking to the Naval Academy, restaurants and the marina. Can’t wait for our next visit.
Stayed 4 nights in Aug 2025

10/10 Excellent

Dan S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great house. Great location!
Stayed 7 nights in Jun 2025

About the host

Hosted by Owner

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Languages:

English