Entire home
Historic Annapolis Charmer <1Mile to NMC Stadium
Family-friendly holiday home in Annapolis
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Reviews
9.8 out of 10 
Exceptional
6 bedrooms3+ bathroomsSleeps 20464.5 sq m
Popular amenities
Explore the area

Annapolis, MD
- Place, Navy-Marine Corps Memorial Stadium19 min walk
- Place, U.S. Naval Academy4 min drive
- Place, Annapolis City Dock5 min drive
- Airport, Washington, DC (DCA-Ronald Reagan Washington National)48 min drive
Rooms & beds
6 bedrooms (sleeps 20)
Bedroom 1
1 King Bed
Bedroom 2
1 King Bed
Bedroom 3
1 Queen Bed
Bedroom 4
2 Single Beds and 1 Queen Bed
Bedroom 5
1 King Bed
Bedroom 6
1 King Bed
Living Room 1
1 Queen Bed
Living Room 2
1 King Bed
Living Room 3
1 Double Bed
3 bathrooms, 2 half bathrooms
Guest Bathroom
Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer
Guest House Bathroom
Soap · Towels provided · Bathtub or shower · Bathtub · Toilet · Shampoo · Hair dryer
Main House Basement Half Bath
Soap · Towels provided · Toilet
Main House First Floor Half Bath
Soap · Towels provided · Toilet
Master Bathroom
Soap · Towels provided · Bathtub or shower · Bathtub · Toilet · Shampoo · Hair dryer
Spaces
Deck or patio
Porch or lanai
Kitchen
Balcony
Separate dining area
Outdoor play area
Garden
Dining area
About this property
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!
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!
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Amenities
Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning
Outdoor space
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9.4 out of 10, (17 reviews)
House Rules
Check in after 4:00 PM 
Minimum age to rent: 24 
Check out before 11:00 AM 
Children
Children allowed: ages 0–17 
Events
No events allowed 
Pets
No pets allowed 
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
Long-term renters welcome
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
Annapolis is home to this holiday home. The area's natural beauty can be seen at Jonas Green State Park and Smithsonian Environmental Research Center, while Maryland Hall for Creative Arts and Ballet Theater of Maryland are cultural highlights. Travelling with kids? Consider Helen Avalynne Tawes Garden, or check out an event or a game at Navy-Marine Corps Memorial Stadium. Kayaking and waterskiing offer great chances to get out on the surrounding water, or you can seek out an adventure with mountain biking and hiking/biking trails nearby. 

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
- Westfield Annapolis Mall - 4 min drive - 2.8 km
- Annapolis City Dock - 5 min drive - 3.2 km
Getting around
Restaurants
- McDonald's - 13 min walk
- Burger King - 14 min walk
- Dunkin' - 15 min walk
- Taco Bell - 5 min walk
- Wendy's - 14 min walk
Frequently asked questions
Reviews
9.8
Exceptional
9.8/10
Cleanliness
10/10
Check-in
10/10
Communication
10/10
Location
9.4/10
Listing accuracy
Reviews
22 February 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 5 nights in Feb 2024
10/10 Excellent
Nancy H.
11 September 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Wedding Weekend for Our Daughter
Nancy H.
Stayed 3 nights in Sep 2024
8/10 Good
Annie O.
26 August 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Family Wedding
Annie O.
Stayed 2 nights in Aug 2024
10/10 Excellent
Kathlyn F.
18 August 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay at 1603 West St
Kathlyn F.
Stayed 2 nights in Aug 2024
10/10 Excellent
Alison V.
23 March 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Spring Break Getaway
Alison V.
Stayed 3 nights in Mar 2024
10/10 Excellent
Priscilla M.
12 February 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect for large group
Priscilla M.
Stayed 1 night in Feb 2024
About the host
Hosted by Caitlin Young

We are an active duty Navy family (15 years so far) with a love and affinity for Annapolis, the Naval Academy, and Navy Football!  2008 Naval Academy Graduate, we want people to feel right at home in Annapolis when they stay at our property.
Why they chose this property
We chose to list our home because want people to enjoy Annapolis as much as we do. When traveling we often travel with children or other couples for a group getaway and like the ease of a home rental.
What makes this property unique
Guests will have access to private parking, short walk/uber/drive to Downtown Annapolis, Naval Academy, and Navy-MC Stadium and a quiet  Guest House with own entry that will be the perfect Historic Annapolis get Aweigh spot.  We have everything you need to have your home away from home, so pack light and enjoy your stay!
Languages:
English
Premier Host
They consistently provide great experiences for their guests
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