You'll have the entire home to yourself and will only share it with other guests in your party.
Historic Annapolis Charmer <1Mile to NMC Stadium
IMMACULATE SPACE AND RARE FIND IN DOWNTOWN ANNAPOLIS SLEEPING UP TO 12! Beautifully maintained 1930's home in the middle of Annapolis. Right outside of the hustle and bustle but walking distance to everything. Added bonus of parking for 5+ on site.
This is a split unit with 4BR 3 BA 1 Half Bath in the Main House and 1BR 1 BA in the Carriage House. Perfect for Wedding Parties, multi-family stays, the holidays. THE PERFECT SETUP for Commissioning Week or Reunion Weekends.*NEW* PLAN YOUR NEXT BIRTHDAY GET TOGETHER, WEDDING REHEARSAL DINNER, REUNION, HOLIDAY FUNCTION, OR NAVAL ACADEMY FOOTBALL OR ALUMNI FUNCTION AT THE CHARMER! WILL NOT FIND A PLACE THIS SIZE OR THIS IMMACULATE IN AND AROUND DOWNTON ANNAPOLIS!
This beautiful early 1900’s home is the unique space to host a myriad of different events. Boasting 5 bedrooms spanned across the Main House (4 BR 2 BA 2 Half Bath) and Guest House (1 BR 1 BA) sleeping up to 21! You will not find a space this large and this immaculate in and around Downtown Annapolis!!!
Charming Main house - a 10-15 min walk to Navy Marine Corps Stadium / a 5 min drive from the Naval Academy and Downtown Annapolis! Perfect for families with MIDN at USNA or alums in town for a football game or reunion event. There is also ample off street parking (driveway easily fits 5 cars) at the property as well as free on street parking for large groups. Multiple level sleeping makes it great for multi-generations traveling together.
The first floor has a living room and sun room, a half bath, and kitchen with a large dining space to comfortably seat 10 people. Sun room couch converts into a full size sleeper sofa.
The second floor has 4 bedrooms - a master bedroom suite with ensuite bathroom. The other three bedrooms share a full non-master bathroom.
Finished basement is perfect for lounging and can be a separate sleeping space (sofa and keg size day bed) with half bath.
Outdoor includes front porch with lounge seating, covered back porch with lounge seating and string lighting perfect for dining. Propane gas grill available at the main house.
Quaint Guest House - First Floor entry has seating and small storage for extra bags/luggage. Up the stairs to the second floor leads to the kitchen with all amenities of home, breakfast nook seating for up to 7.
Off the kitchen is a covered back porch with lounge seating and string lighting.
Living room has large sectional sofa, TV, and table seating for guests comfort and enjoyment. Rollout bed is available in back bedroom closet, and living room couch folds out into a full size bed.
Each bedroom has a king size bed and television. These bedrooms share a large oversized bathroom with double vanity. Stackable washer dryer also located in bathroom.
Outdoor space is PERFECT for lounging, hosting a bbq or dinner (two separate gas grills), or having a private event. Large driveway and oversized backyard which includes covered second story deck with lounge seating, fans, and string lighting. Covered backyard patio area with large dining table with seating for 6 and outdoor tv for watching the game. Another uncovered concrete patio with table seating for 6, as well as a propane fire pit with lounge seating for 6 around it as well along with automatic outdoor landscape lighting to keep the event going after the sun goes down!
5+ parking spaces on site with free street parking on adjacent streets. Driveway and paths are lit. Guests will receive unique private code prior to check-in for use on their front and rear private entrances. Guests are able to access both front and rear porches and backyard spaces.
Each door is equipped with a keypad. The code will be provided day of check-in. Lighted driveway and pathways for ease of entry
We charge for additional guests above a fixed amount. This amount and additional charge varies by unit type, size, and configuration. If you input the correct guest count when you make your reservation the amount the booking site indicated as the total cost will not change (due to guest count). We ask for confirmation of guest count after you complete your booking. If you need to increase your guest count after booking confirmation due to a booking error, this could result in a price increase. Finally, we verify guest count via external cameras located on our properties. In the event that we notice a guest count at the property that is higher than reported, we reserve the right to ask for additional guest fees that would be double the amount we would have charged prior to check-in.
The following additional charges may apply to late check outs/early arrivals, assuming I can offer this at all (I often can’t so please never assume this will be allowed):
1 hr or less early arrival or late departure: $100 1-2 hr early arrival/late departure: $200 2-3 hr early arrival/late departure: $300 3+ hr early arrival/late departure: $100/hr or the cost of an additional night’s stay, whichever is more
These fees are primarily in place to highly discourage late checkouts/early arrivals since this causes my cleaning service undue stress to prep the unit prior to your or the next set of guest’s arrival. This also increases the need for them to rush/cut corners, increasing the likelihood of them not cleaning the unit to the high standard which I hold them to.
***Smoking is strictly forbidden anywhere on the property - the house, front porch, back deck, or front or back yard***
***If we find cigar/cigarette butts of any kind on the property or evidence of smoking (ash on porch, deck, empty cigarette packs, etc.) We assess a $500 cleaning fee in addition to the regular cleaning fee***
We are here to assist should you have questions. Feel free to message us!
Property manager
Caitlin Young
Languages
English
Add dates for prices
Property amenities
Internet
Available in the house: Free WiFi
Parking and transportation
Onsite parking options include a garage
Kitchen
Blender
Coffee/tea maker
Cookware, dishware, and utensils
Dishwasher
Ice maker
Kitchen island
Microwave
Oven
Paper towels
Refrigerator
Spices
Stovetop
Toaster
Dining
Dining table
Bedrooms
6 bedrooms
Bedsheets provided
Bathroom
4 bathrooms
Bathtub or shower
Hair dryer
Shampoo
Shower
Soap
Toilet paper
Towels provided
Living spaces
Dining table
Fireplace
Living room
Separate dining area
Entertainment
Games
Smart TV
Outdoor areas
Balcony
Firepit
Garden
Gas grill
Outdoor furniture
Laundry
Laundry facilities
Washing machine
Work spaces
Computer monitor
Desk
Desk chair
Comfort
Air conditioning
Heating
Pets
No pets allowed
Suitability/Accessibility
Smoking not allowed
Services and conveniences
Iron/ironing board
Location highlights
Near a hospital
Near an outlet shopping mall
Near the marina
Things to do
Arcade/game room
Billiards/pool table
Foosball table
Table tennis
Water park
Basketball nearby
Fishing nearby
Golfing nearby
Hiking/biking trails nearby
Kayaking nearby
Motor boating nearby
Mountain biking nearby
Sailing nearby
Swimming nearby
Water skiing nearby
Water tubing nearby
Wildlife walks nearby
Safety features
Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
Smoke detector (host has indicated there is a smoke detector on the property)
First aid kit
Fire extinguisher
Deadbolt lock
General
Garden
Unit size: 5,000 square feet
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You will receive an email from the host with check-in and check-out instructions
Pets
Pets not allowed
Children and extra beds
Children are welcome
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
Onsite parties or group events are strictly prohibited
Long-term renters welcome
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
About the neighborhood
Annapolis, MD
What's nearby
Navy-Marine Corps Memorial Stadium - 19 min walk - 1.6 km
Anne Arundel Medical Center - 3 min drive - 2.5 km
U.S. Naval Academy - 4 min drive - 2.8 km
Annapolis Mall Shopping Center - 4 min drive - 2.8 km
Annapolis City Dock - 5 min drive - 3.2 km
Getting around
Odenton Station - 19 min drive
Fort Meade, MD (FME-Tipton) - 26 min drive
Restaurants
Chick-fil-A - 3 min drive
McDonald's - 14 min walk
Taco Bell - 5 min walk
Double T Diner - 2 min drive
Burger King - 14 min walk
Frequently asked questions
Is Historic Annapolis Charmer <1Mile to NMC Stadium pet-friendly?
No, pets are not allowed at this property.
How much does it cost to stay at Historic Annapolis Charmer <1Mile to NMC Stadium?
As of 30 June 2025, prices found for a 1-night stay for 2 adults at Historic Annapolis Charmer <1Mile to NMC Stadium on 1 July 2025 start from $1,151.31, 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.
What time is check-in at Historic Annapolis Charmer <1Mile to NMC Stadium?
Check-in begins at 4:00 PM.
What time is check-out at Historic Annapolis Charmer <1Mile to NMC Stadium?
Check-out is at 11:00 AM.
Where is Historic Annapolis Charmer <1Mile to NMC Stadium located?
This family-friendly Annapolis vacation home is within 1 mi (2 km) of Dr. Aris T. Allen Memorial, Helen Avalynne Tawes Garden, and Maryland Hall for Creative Arts. U.S. Naval Academy is 2 mi (3.3 km) away.
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Historic Annapolis Charmer <1Mile to NMC Stadium Reviews
Reviews
9.8
Exceptional
All reviews shown are from real guest experiences. Only travelers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
Rating 10 - Excellent. 5 out of 6 reviews
10 - Excellent
5
Rating 8 - Good. 1 out of 6 reviews
8 - Good
1
Rating 6 - Okay. 0 out of 6 reviews
6 - Okay
0
Rating 4 - Poor. 0 out of 6 reviews
4 - Poor
0
Rating 2 - Terrible. 0 out of 6 reviews
2 - Terrible
0
9.8/10
Cleanliness
Reviews
10/10
The home was beautiful and spacious. The host was wonderful and communicated with us very well.
Would recommended for a large group!
Kathlyn F.
Stayed 2 nights in Aug 2024
10/10
We had 11 people in our group and this house was the perfect size for gathering and sleeping comfortably. Great accommodations, easy to get downtown and around. Definitely recommend
Priscilla M.
Stayed 1 night in Feb 2024
10/10
Our lacrosse team loved our recent stay! The host is amazing and their home is beautiful and comfortable. Great location close to Annapolis harbor and easy access to the highway. Zero complaints; we only wish we could have stayed longer!
Alison V.
Stayed 3 nights in Mar 2024
10/10
We rented this property for three nights for our daughters wedding at CBF and related festivities in Annapolis Downtown. The property was extremely well located and it took minutes to get to and from any place that we needed to get to. It provided an adequate amount of space for all of our needs. Family time was our goal and this property made it possible to host them and have everyone feel comfortable and relax. The backyard space is amazing and I only wish we'd had more time to hang there. Thinking of renting this property again to bring family to such a fun town for a long weekend vacation. Thanks for your quick responses and for making our stay memorable!!
Nancy H.
Stayed 3 nights in Sep 2024
10/10
Our whole family descended upon Annapolis for my son’s wedding week. We have five adult children - two that are married plus our siblings and their spouses. (17 total) We wanted to all stay together so that we could enjoy the festivities in a home setting instead of a hotel. This place worked perfectly! We were coming from Florida, Colorado, Missouri, Alabama, Kentucky, and Oklahoma. Our son graduated from the enable Academy in 2019 and they had a wedding ceremony on the yard. This place was conveniently located to the ceremony as well as different things we did in downtown Annapolis.
With so many bedrooms, we were able to each spread out and have our individual time, but also gather together in the family areas or go for walks, or even eat meals together. Communication was excellent and we were provided with everything that we needed for our stay. I would highly recommend this place for your family gathering! Clean, beautifully decorated and provides lots of space even for four different rental cars.
Tina k.
Stayed 5 nights in Feb 2024
8/10
We chose the house because our pretty large family was coming in from across the country for a wedding. The house was as advertised, spacious with enough king beds to accommodate 4 adult couples and good TV connections to access movies for the young children. Communication with the hosts was clear, helpful and prompt. I would recommend renting this house.