Be our guest at Historic 19 East Street, in the heart of the Annapolis national landmark district. Walk out the front door, look left and see the iconic Maryland State House, look right and you're less than a block from Gate One of the United States Naval Academy. St. John's College, St. Mary's, City Dock, William Paca Gardens, and Main Street are all within three blocks. Everything Historic Annapolis has to offer, from boating to restaurants to shopping to Naval Academy traditions, is yours to enjoy!
Historic 19 East is the perfect location for weddings, USNA events, regattas or just a quiet getaway. The interior of this exceptionally restored 115 year old home is perfectly updated, light, friendly, and beyond comfortable with hard wood floors throughout, a large flat screen 4K TV in the living room. Gather around our large dining room table for family meals, or enjoy the very large, privately fenced bricked patio for a cook-out, brunch or cocktail after a full day of exploring the town. If you don't feel like cooking order take-out or stroll to one of the many renowned local eateries. The coffee maker is a Keurig for ease of making single cups. Our home comfortably sleeps 6 (two queens, one full, one twin) and is perfect for a family gathering, weekend getaway or a reunion among friends. It is a wonderful property in a fantastic location and we look forward to you being our guest. LIMITED PARKING: In order to help residents and visitors navigate parking downtown, a website www.AccessAnnapolis.com was created to serve as a hub for parking and transit information to help residents, businesses, employees, customers, and visitors plan their visit to downtown Annapolis. You may find more options by googling Annapolis Parking. Once you park your car you will be set on foot to explore all that Annapolis has to offer.
USING PARK MOBILE: Non-residents are encouraged to download the ParkMobile app (Android/Apple). After the app has been downloaded, add your vehicle tag, payment method and allow “location enabled services” to automatically determine ParkMobile parking zone data. Parking can also be paid by texting “PARK” to 77223.
TAXES: VRBO collects and pays a 6% Sales and Use Tax required by Anne Arundel County. In addition, the owners must collect and pay a City of Annapolis Hotel and Motel Tax of 7% which is listed in the rates section as a "Property Fee." Please let us know if you have any questions about these taxes. Short Term License: STR-142633
Suitability: Non-smoking only, wheelchair inaccessible, no pets, 25 or older please.
Add dates for prices
Have a question?
AI iconBetaBeta
Get instant answers with AI powered search of property information and reviews.
Similar properties
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Historic District
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
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, a first aid kit and a deadlock
About the area
Annapolis
Located in Historic District, a neighbourhood in Annapolis, this holiday home is near theme parks. The area's natural beauty can be seen at Chesapeake Bay and Jonas Green State Park, while The Colonial Players and Hammond-Harwood House are cultural highlights. French Soldiers Monument and Helen Avalynne Tawes Garden are also worth visiting. Kayaking, power boating and sailing offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling nearby.
O'Brien's Oyster Bar & Seafood Tavern - 5 min walk
Annapolis Market House - 4 min walk
Chick & Ruth's Delly - 6 min walk
Frequently asked questions
Is PERFECT LOCATION in the heart of history pet-friendly?
No, pets are not allowed at this property.
How much does it cost to stay at PERFECT LOCATION in the heart of history?
As of 11 May, 2026, prices found for a 1-night stay for 2 adults at PERFECT LOCATION in the heart of history on 29 Jul, 2026 start from S$507, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
How much is parking at PERFECT LOCATION in the heart of history?
On-site parking is available at the property.
What time is check-in at PERFECT LOCATION in the heart of history?
Check-in begins at 3:00 PM.
What time is check-out at PERFECT LOCATION in the heart of history?
Checkout is at 11:00 AM.
Where is PERFECT LOCATION in the heart of history located?
Located in Historic District, this holiday home is steps away from U.S. Naval Academy, John Smith House and William Paca House. Annapolis City Dock and 14 Fleet Street are just steps away.
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Perfect stay and perfect location in Annapolis. The home is very well appointed and comfortable. The owners are extremely kind and communicative. Parking can be a little tricky, but they provide great insight on how to set up for success, and everything is walkable once you get your car parked. Would 100% stay here again. Awesome experience!
Great house, great location especially if you’re going to the Naval Academy or downtown/ waterfront both are steps away! 5 minute walk gets you to more than a dozen excellent restaurants and bars, shopping and more. Owner was very accommodating for some little chnages on our plans. Would definitely return!
Literally feels like home. So refreshing to work with quality owners and walk into a clean, delightful place. Every time we had a question or request, it was answered quickly and professionally. Very much appreciate our time here.
Would give more stars if we could!!! Every interaction before, during and after was the ultimate professional interaction. Literally all details were thought of and taken care of prior to our arrival. This property was clean, well laid out, and 'turn key' ready so we could focus on time with our midshipmen. Excellent stay here and beyond perfect!
Great property with an awesome location to both the Yard and DTA! Property manager and owners very easy to work with and checked in just enough to make sure everywas to our satisfaction. Great stay!
The property is in such a great location. It is very clean and roomy. it is a beautiful historical home with modern amenities. Scott is such a great host, very responsive and accommodating. My family would definitely stay there again!
The host was very accommodating and responsive. The house is in a great location and the listing is accurate. Loved our stay and will definitely be booking again!
A very comfortable and quiet stay in the heart of Annapolis. Checking in was simple and hassle-free. Steps to USNA, Ego Alley, and shops on Maryland Ave. Parked at the public garage just off Main St, no issues and only a few minutes away by foot.
We had a great stay and the property worked out perfectly for my son’s wedding. Close to the wedding venue and after party down by the dock. Really was the right size for myself, my daughter, son in law and three grandchildren.
Adorable, well-appointed place in the heart of Annapolis. Awesome neighborhood just the right distance from the crowded more touristy areas (yet quite walkable to all!) Great for three couples for the weekend. Easy in and out with a nearby (free on weekend) parking deck that felt like a way better bet than street parking. We loved it.
As a family, we served over 20 years in the Navy. Scott flew F/A-18's deploying 5 times supporting global operations and had the privilege of flying one tour with the US Navy Blue Angels. We moved 14 times in 20 years and understand the joy of a quality home.
Why they chose this property
We purchased this property after staying in it during USNA Induction Day 2015. We fell in the love with the home and all of the wonderful aspects of historic Annapolis.
What makes this property unique
After purchasing the home we updated the kitchen with high-end stainless steel appliances, granite countertops, freshly painted throughout, and refinished the 100 year old hardwood floors. The home's location is perfect for any visitor to Annapolis, whether your travels bring you for a romantic weekend, a family reunion, or one for USNA festivities. The location is hard to beat. It is steps away from all the activity, be it downtown or on the Yard. We fell in love it and we know you will too. We look forward to having you as our guest.
Languages:
English
Premier Host
They consistently provide great experiences for their guests