Historic Downtown Charmer, Water Views and Parking!

Annapolis, Maryland
$425 avg/night Minimum Stay 2 Nights
Bed 2

Bed

Bath 1

Bath

Home Private Vacation Home

Property Type

Sleep 5

Max Sleeps

Night 2 nights

Min Stay

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 alongEgo 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.

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  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Deadbolt Lock Fire Extinguisher Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    2 Bedrooms Bed Sheets Provided
  • GENERAL

    Recycling
  • KITCHEN

    Blender Dishwasher Ice Maker Microwave Oven Paper Towels Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Near Laundromat Washing Machine And Dryer
  • PARKING

    Car Not Required Onsite Parking
  • INTERNET

    WiFi Available
  • OUTDOORS

    Balcony
  • BATHROOMS

    1.5 Bathrooms Bathtub Or Shower Hair Dryer Shampoo Soap Toilet Paper Towels Provided
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Basketball Nearby Birdwatching Nearby Cycling Nearby Fitness Facilities Nearby Golf Nearby Hiking Nearby Marina Nearby Power Boating Nearby Swimming Nearby Windsurfing Nearby
  • ENTERTAINMENT

    TV With Cable/satellite Service
  • LIVING SPACES

    Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • LOCATION HIGHLIGHTS

    In The City Center Near A Health Or Beauty Spa Near A Hospital Near Outlet Shopping
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 11:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 5

Map Map

School District Availability

Review Review

  • Rosemary R.

    Submitted Dec 17, 2025

    Stayed Dec 12, 2025

    Very responsive host! Appreciated the great communication.

  • Patrizia P.

    Submitted Nov 18, 2025

    Stayed Nov 14, 2025

    Everything was great

  • Kathy O.

    Submitted Nov 10, 2025

    Stayed Nov 6, 2025

    Very comfortable, clean, nicely decorated home just steps away from the market & USNA. Perfect for our reunion weekend!

  • John M.

    Submitted Oct 27, 2025

    Stayed Oct 23, 2025

    Great location for all Naval Academy activities!! Patricia's instructions were clear and very helpful and she was very accommodating on check-in time.

  • Susan C.

    Submitted Oct 20, 2025

    Stayed Oct 17, 2025

    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.

  • Angela S.

    Submitted Sep 30, 2025

    Stayed Sep 26, 2025

    Great location and very nice place. Owner was very friendly and responsive.

  • lovada a.

    Submitted Sep 22, 2025

    Stayed Sep 18, 2025

    Carpeting on the second floor is in desperate need of cleaning or replacing. Not healthy.

  • ana c.

    Submitted Sep 8, 2025

    Stayed Sep 4, 2025

    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.

  • Theresa R.

    Submitted Sep 3, 2025

    Stayed Aug 22, 2025

    Excellent location! Owner is very responsive and helpful

  • Lorraine K.

    Submitted Sep 2, 2025

    Stayed Aug 29, 2025

    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.

  • Paul H.

    Submitted Aug 18, 2025

    Stayed Aug 15, 2025

    Lovely Annapolis home in a great location

  • Tom M.

    Submitted Aug 11, 2025

    Stayed Aug 7, 2025

    Great place in DTA - perfect location for walking to the Naval Academy, restaurants and the marina. Can’t wait for our next visit.

  • Michelle W.

    Submitted Aug 4, 2025

    Stayed Jul 31, 2025

    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.

  • Dan S.

    Submitted Jul 26, 2025

    Stayed Jun 29, 2025

    Great house. Great location!

  • Lisa P.

    Submitted Jul 9, 2025

    Stayed Jun 24, 2025

    This property is the perfect location for accessing the Naval Academy. We stayed here for our I-Day drop-off. The close proximity to the Naval Academy made it possible to return here for a much needed cool down and rest between drop-off, parent expo, and induction ceremony on a very hot day (temps in the mid to upper 90's). A rare feature of this property is a gated private parking space. No need to pay extra for parking your car in DTA.

  • Submitted Jun 9, 2025

    Stayed May 30, 2025

    Excellent location, walking distance to the Naval Academy, beautiful home and owner was super easy to work with. We would definitely book again!

  • Nganming M.

    Submitted May 11, 2025

    Stayed May 9, 2025

    Communication with Patricia was great. She responded my call and texts in a reasonable time. The house is next to the city dock and the main shopping, restaurant area. Close to the navy academy. I was able to walk to all the places I wanted to go. AC works without an issue.

  • MARTY D.

    Submitted May 9, 2025

    Stayed Apr 8, 2025

    We loved it. It was perfect for us & the location was great! We had no problems at all!

  • Sandra W.

    Submitted Jan 2, 2025

    Stayed Dec 16, 2024

    Very nice location. Very comfortable and clean. I would stay again.

  • Erin S.

    Submitted Nov 28, 2024

    Stayed Nov 14, 2024

    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.

  • Philip B.

    Submitted Oct 31, 2024

    Stayed Oct 25, 2024

    Good communication, perfect location and a parking space was a real bonus.

  • Tim N.

    Submitted Oct 19, 2024

    Stayed Oct 17, 2024

    Fantastic location, only a short walk to the main gate of the academy. Warm comfortable and clean! The deck on the top of the building gave spectacular views of Annapolis Harbor and we thoroughly enjoyed our stay! Made the 40th reunion extra special for my lovely wife and I whom I met in Annapolis 43 years ago. Thanks so much!

  • Robert W.

    Submitted Oct 9, 2024

    Stayed Oct 4, 2024

    Good weekend getaway

  • Earl K.

    Submitted Sep 28, 2024

    Stayed Sep 26, 2024

    Location, accommodations were top-notch

  • Susan W.

    Submitted Sep 8, 2024

    Stayed Sep 5, 2024

    Perfect location with parking! We could walk everywhere without the hassle of moving our car! Kitchen had everything you needed if you wanted to cook. Comfortable beds!

  • tiffany H.

    Submitted Sep 1, 2024

    Stayed Aug 30, 2024

    A wonderful property in the heart of Annapolis outfitted with all the items to make your stay easy and enjoyable. Park when you arrive and walk the rest of your stay. Property was very clean and nicely outfitted. We can’t wait to go back!

  • Felder B.

    Submitted Aug 23, 2024

    Stayed Aug 8, 2024

    We enjoyed staying in this property and it was as advertised and close to everything. We were able to walk everywhere downtown and to the Naval Academy in 3 minutes. The owners were great to deal with and responded promptly to our questions. No problems and enjoyed our stay.

  • Lewis H.

    Submitted Jul 23, 2024

    Stayed Jul 12, 2024

    The location can’t be beat.

  • Tammy P.

    Submitted Jul 18, 2024

    Stayed Jun 24, 2024

    Loved our stay at this beautiful townhome with a he rooftop deck. Perfect location around the corner from Iron Rooster. Patty was the perfect host — very responsive. Place has everything we needed. Hope to stay in the future.

  • john e.

    Submitted Jul 7, 2024

    Stayed Jul 5, 2024

    Awesome stay!! Everything you could want and location is great ?

  • Kristen S.

    Submitted Jun 10, 2024

    Stayed Jun 7, 2024

    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!

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Total

Includes taxes and fees
$425+
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