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Historic Happy Home Steps from Main Street – Private Yard, Screened-In Porch & Parking
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Reviews
10 out of 10, Loved by Guests
Top 10% of guest reviews in this area
3 bedrooms2+ bathroomsSleeps 82550 sq ft
Popular amenities
Explore the area

Annapolis, MD
- Place, Maryland State House5 min walk
- Place, Annapolis City Dock6 min walk
- Place, U.S. Naval Academy8 min walk
- Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)32 min drive
Rooms & beds
3 bedrooms (sleeps 8)
2nd Floor Full
1 Double Bed
2nd Floor King
1 King Bed
3rd Floor Suite
1 Queen Bed
Living Room
1 Queen Sofa Bed
2 bathrooms, 1 half bathroom
Main Floor Powder Room
Toilet
Second Floor Hall
Bathtub · Toilet · Shower only
Third Floor Queen
Toilet · Shower only
Spaces
Deck or patio
Kitchen
Garden
About this property
Historic Happy Home Steps from Main Street – Private Yard, Screened-In Porch & Parking
Experience the Difference: Professionally Managed by iTrip Annapolis
Enjoy a piece of Annapolis history! Nestled at the end of a row, this circa 1879 home has the perfect blend of historic cedar shake charm on the outside combined with a surprisingly modern interior. The renovated kitchen with its exposed brick chimney, beautiful cabinets, granite countertops and breakfast bar overlooks the sunken great room with walls of windows and cathedral ceilings. Celebrate your Happy Hours on the spacious screened porch overlooking the private backyard. Back inside is a dining room with seating for 8 and bright living room in the front of the home with a new Queen sleeper sofa. There is also a powder room and full laundry room located on the main floor.
Head upstairs to the 3 oversized bedrooms and 2 bathrooms. The 2 guest bedrooms on the 2nd floor share the unique full bath in the hall, with separate shower/bath and double vanity/toilet rooms. The third-floor suite has a Queen bed, its own private full bath and even a delightful peek-a-boo view of the Maryland State House. Located one block to the quiet waters of Spa Creek and 2 blocks to Main Street, this home is just steps away from downtown shopping, restaurants, parks and historical sites, the Naval Academy and the Maryland State House.
***Parking is not on premises!! A dedicated parking spot at NEARBY GARAGE (10 minute walk) is provided. Please contact us for details.
SLEEPING ARRANGEMENTS 3 BR / 2.5 BA / Sleeps 8:
3rd Floor Suite:
- Queen Bed
- Full ensuite bath with stand-up shower
King Bedroom:
- 2nd Floor
- King Bed
- Full bath in the hall with standup shower and soaking tub, double vanity
Full Bedroom:
- 2nd Floor
- Full Bed
- Full bath in the hall with standup shower and soaking tub, double vanity
Living Room
- Main Floor
- Queen sleeper sofa
- Half bath on the main floor; shared full bath in the hall on the 2nd floor
HIGHLIGHTS:
- Large Kitchen overlooking the sunny sunken den
- Breakfast bar in kitchen seats 2
- Dining room table seats 8
- Large screened-in porch
- Private backyard
- WiFi
- Big Screen Smart TV's
- 2 bicycles for guest use
- Luxury linens, complimentary toiletries Starter Kit, and boutique-level service
- Keurig and coffee pot with starter coffee and creamers
- Washer & dryer located inside the home
- Elderly and guests with mobility issues may want to inquire about the steep staircase and/or may want to consider other accommodations.
- Keyless entry. Drive straight to your rental home and enter the code for the electronic lock on the front door.
Property Distance to:
- U.S. Naval Academy – 5 blocks
- Washington, DC – 30 miles
- Baltimore - 25 miles
* Amenity & Supplies starter pack, coffee and sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid to get you going.
* All beds are ready made for you with freshly laundered sheets & towels.
House Rules
Reservations made for teenagers or young single groups will not be honored without any accompanying adult staying in the unit at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No smoking/no pets. Please respect the neighbors and neighborhood. No parties, events or smoking of any kind.
Check-in time: 4:00 pm
Check-out time: 11:00 am
Enjoy a piece of Annapolis history! Nestled at the end of a row, this circa 1879 home has the perfect blend of historic cedar shake charm on the outside combined with a surprisingly modern interior. The renovated kitchen with its exposed brick chimney, beautiful cabinets, granite countertops and breakfast bar overlooks the sunken great room with walls of windows and cathedral ceilings. Celebrate your Happy Hours on the spacious screened porch overlooking the private backyard. Back inside is a dining room with seating for 8 and bright living room in the front of the home with a new Queen sleeper sofa. There is also a powder room and full laundry room located on the main floor.
Head upstairs to the 3 oversized bedrooms and 2 bathrooms. The 2 guest bedrooms on the 2nd floor share the unique full bath in the hall, with separate shower/bath and double vanity/toilet rooms. The third-floor suite has a Queen bed, its own private full bath and even a delightful peek-a-boo view of the Maryland State House. Located one block to the quiet waters of Spa Creek and 2 blocks to Main Street, this home is just steps away from downtown shopping, restaurants, parks and historical sites, the Naval Academy and the Maryland State House.
***Parking is not on premises!! A dedicated parking spot at NEARBY GARAGE (10 minute walk) is provided. Please contact us for details.
SLEEPING ARRANGEMENTS 3 BR / 2.5 BA / Sleeps 8:
3rd Floor Suite:
- Queen Bed
- Full ensuite bath with stand-up shower
King Bedroom:
- 2nd Floor
- King Bed
- Full bath in the hall with standup shower and soaking tub, double vanity
Full Bedroom:
- 2nd Floor
- Full Bed
- Full bath in the hall with standup shower and soaking tub, double vanity
Living Room
- Main Floor
- Queen sleeper sofa
- Half bath on the main floor; shared full bath in the hall on the 2nd floor
HIGHLIGHTS:
- Large Kitchen overlooking the sunny sunken den
- Breakfast bar in kitchen seats 2
- Dining room table seats 8
- Large screened-in porch
- Private backyard
- WiFi
- Big Screen Smart TV's
- 2 bicycles for guest use
- Luxury linens, complimentary toiletries Starter Kit, and boutique-level service
- Keurig and coffee pot with starter coffee and creamers
- Washer & dryer located inside the home
- Elderly and guests with mobility issues may want to inquire about the steep staircase and/or may want to consider other accommodations.
- Keyless entry. Drive straight to your rental home and enter the code for the electronic lock on the front door.
Property Distance to:
- U.S. Naval Academy – 5 blocks
- Washington, DC – 30 miles
- Baltimore - 25 miles
* Amenity & Supplies starter pack, coffee and sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid to get you going.
* All beds are ready made for you with freshly laundered sheets & towels.
House Rules
Reservations made for teenagers or young single groups will not be honored without any accompanying adult staying in the unit at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No smoking/no pets. Please respect the neighbors and neighborhood. No parties, events or smoking of any kind.
Check-in time: 4:00 pm
Check-out time: 11:00 am
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House Rules
Check in after 4:00 PM
Minimum age to rent: 25
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
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
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
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 wishing to experience the area's natural beauty can explore Jonas Green State Park and Sandy Point State Park. Looking to enjoy an event or a game while in town? See what's happening at Tose Family Tennis Center or Alumni Hall.

Annapolis, MD
What's nearby
- Maryland State House - 5 min walk - 0.4 km
- Annapolis City Dock - 6 min walk - 0.6 km
- William Paca House - 8 min walk - 0.7 km
- U.S. Naval Academy - 8 min walk - 0.7 km
- Ego Alley - 8 min walk - 0.7 km
Getting around
Restaurants
- Starbucks - 5 min walk
- Rams Head Tavern - 7 min walk
- O'Brien's Oyster Bar & Seafood Tavern - 5 min walk
- Buddy's Crabs & Ribs - 5 min walk
- Chick & Ruth's Delly - 3 min walk
Frequently asked questions
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window10/10
Cleanliness
10/10
Check-in
10/10
Communication
10/10
Location
9.8/10
Listing accuracy
Reviews
14 Oct, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 2 nights in Oct 2025
10/10 Excellent
Dana D.
11 Sept, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great Annapolis Location
Dana D.
Stayed 3 nights in Sep 2024
10/10 Excellent
Elizabeth M.
6 Oct, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great trip
Elizabeth M.
Stayed 4 nights in Oct 2024
8/10 Good
James M.
5 Sept, 2025
Liked: Cleanliness, check-in, communication, location
James M.
Stayed 2 nights in Aug 2025
10/10 Excellent
Verified traveller
24 Jun, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location!
Verified traveller
Stayed 3 nights in Jun 2023
10/10 Excellent
shannon r.
25 Dec, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location and cute property
shannon r.
Stayed 2 nights in Dec 2024
10/10 Excellent
Lisa R.
16 Aug, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Awesome stay!
Lisa R.
Stayed 4 nights in Aug 2023
10/10 Excellent
Colleen M.
2 Dec, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Charming house with great location
Colleen M.
Stayed 3 nights in Nov 2024
10/10 Excellent
Nancy W.
12 Nov, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
60th birthday celebration weekend
Nancy W.
Stayed 2 nights in Nov 2024
10/10 Excellent
Skyler G.
30 Jun, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect Stay
Skyler G.
Stayed 3 nights in Jun 2024
10/10 Excellent
Gregory K.
3 Apr, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great house
Gregory K.
Stayed 2 nights in Mar 2023
10/10 Excellent
katherine w.
20 Sept, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Had a great time!
katherine w.
Stayed 2 nights in Sep 2023
This review is from a guest who booked and stayed through a partner site and can't be verified.
10/10 Excellent
Kelly S.
16 Jul, 2023
Best Place to Stay in Annapolis!
Kelly S.
10/10 Excellent
Catherine W.
22 Nov, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Wedding house rental
Catherine W.
Stayed 4 nights in Nov 2024
10/10 Excellent
Karry G.
27 Mar, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Location and comfort
Karry G.
Stayed 2 nights in Mar 2023
10/10 Excellent
Kathy C.
12 Jun, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Cute, Historical and Convenient
Kathy C.
Stayed 2 nights in Jun 2024
10/10 Excellent
William E.
23 Aug, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect for USNA Visit
William E.
Stayed 4 nights in Aug 2024
10/10 Excellent
Kelly J.
9 Nov, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Historic and perfectly situated
Kelly J.
Stayed 2 nights in Nov 2023
10/10 Excellent
Donald E.
5 May, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Fantastic location and house
Donald E.
Stayed 2 nights in May 2024
10/10 Excellent
Alicia H.
29 Oct, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Fall Weekend USNA
Alicia H.
Stayed 2 nights in Oct 2023
10/10 Excellent
Russell P.
16 May, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Exactly what you are looking for
Russell P.
Stayed 2 nights in May 2023
10/10 Excellent
Jeff & Heather W.
12 Sept, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Will be back!!!
Jeff & Heather W.
Stayed 3 nights in Sep 2023
10/10 Excellent
Dean B.
16 Jun, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great property in Annapolis
Dean B.
Stayed 3 nights in May 2024
10/10 Excellent
Ronda F.
30 Mar, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
This place is so homey! The little extras they add make you feel wanted!
Ronda F.
Stayed 7 nights in Mar 2023
10/10 Excellent
Gordon R.
30 May, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect Annapolis Property
Gordon R.
Stayed 10 nights in May 2023
About the host
Hosted by iTrip Vacations Annapolis - Sean Degnan
Languages:
English
Premier Host
They consistently provide great experiences for their guests
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