Entire home
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
Number of living rooms
Garden
About this property
Historic Happy Home Steps from Main Street – Private Yard, Screened-In Porch & Parking
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- Kitchen
- Washer
- Dryer
- Free WiFi
9.8 out of 10, Exceptional, (50 reviews)
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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
About the neighborhood
Annapolis
Located in Annapolis, this vacation home is in the city center. 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
- Hammond-Harwood House - 9 min walk - 0.8 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 labeled.
Learn moreOpens in a new window10/10
Cleanliness
10/10
Check-in
10/10
Communication
10/10
Location
9.8/10
Listing accuracy
Reviews
Verified
Oct 14, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 2 nights in Oct 2025
Verified
10/10 Excellent
Dana D.
Sep 11, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great Annapolis Location
Dana D.
Stayed 3 nights in Sep 2024
Verified
10/10 Excellent
Elizabeth M.
Oct 6, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great trip
Elizabeth M.
Stayed 4 nights in Oct 2024
Verified
8/10 Good
James M.
Sep 5, 2025
Liked: Cleanliness, check-in, communication, location
James M.
Stayed 2 nights in Aug 2025
Verified
10/10 Excellent
Verified traveler
Jun 24, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location!
Verified traveler
Stayed 3 nights in Jun 2023
Verified
10/10 Excellent
shannon r.
Dec 25, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location and cute property
shannon r.
Stayed 2 nights in Dec 2024
Verified
10/10 Excellent
Lisa R.
Aug 16, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Awesome stay!
Lisa R.
Stayed 4 nights in Aug 2023
Verified
10/10 Excellent
Colleen M.
Dec 2, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Charming house with great location
Colleen M.
Stayed 3 nights in Nov 2024
Verified
10/10 Excellent
Nancy W.
Nov 12, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
60th birthday celebration weekend
Nancy W.
Stayed 2 nights in Nov 2024
Verified
10/10 Excellent
Skyler G.
Jun 30, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect Stay
Skyler G.
Stayed 3 nights in Jun 2024
Verified
10/10 Excellent
Gregory K.
Apr 3, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great house
Gregory K.
Stayed 2 nights in Mar 2023
Verified
10/10 Excellent
katherine w.
Sep 20, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Had a great time!
katherine w.
Stayed 2 nights in Sep 2023
From a partner site
10/10 Excellent
Kelly S.
Jul 16, 2023
Best Place to Stay in Annapolis!
Kelly S.
Verified
10/10 Excellent
Catherine W.
Nov 22, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Wedding house rental
Catherine W.
Stayed 4 nights in Nov 2024
Verified
10/10 Excellent
Karry G.
Mar 27, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Location and comfort
Karry G.
Stayed 2 nights in Mar 2023
Verified
10/10 Excellent
Kathy C.
Jun 12, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Cute, Historical and Convenient
Kathy C.
Stayed 2 nights in Jun 2024
Verified
10/10 Excellent
William E.
Aug 23, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect for USNA Visit
William E.
Stayed 4 nights in Aug 2024
Verified
10/10 Excellent
Kelly J.
Nov 9, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Historic and perfectly situated
Kelly J.
Stayed 2 nights in Nov 2023
Verified
10/10 Excellent
Donald E.
May 5, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Fantastic location and house
Donald E.
Stayed 2 nights in May 2024
Verified
10/10 Excellent
Alicia H.
Oct 29, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Fall Weekend USNA
Alicia H.
Stayed 2 nights in Oct 2023
Verified
10/10 Excellent
Russell P.
May 16, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Exactly what you are looking for
Russell P.
Stayed 2 nights in May 2023
Verified
10/10 Excellent
Jeff & Heather W.
Sep 12, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Will be back!!!
Jeff & Heather W.
Stayed 3 nights in Sep 2023
Verified
10/10 Excellent
Dean B.
Jun 16, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great property in Annapolis
Dean B.
Stayed 3 nights in May 2024
Verified
10/10 Excellent
Ronda F.
Mar 30, 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
Verified
10/10 Excellent
Gordon R.
May 30, 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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