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Photo gallery for Cheerful 3-Bedroom House in Downtown Annapolis





Entire home
3 bedrooms 2 bathrooms Sleeps 8
Popular amenities
Explore the area
Annapolis, MD
- Navy-Marine Corps Memorial Stadium19 min walk
- U.S. Naval Academy2 min drive
- Annapolis City Dock3 min drive
- Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)33 min drive
Room options
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Annapolis Waterfront Hotel, Autograph Collection
Historic District
- Pet friendly
- Free WiFi
- Restaurant
- Air conditioning
4.4 out of 5, Excellent, 843 reviews
$220 nightly
The price is $251
Aug 17 - Aug 18
Total includes taxes and fees
About the neighborhood
About this property
Similar properties

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
- Kitchen
- Washer
- Dryer
- Pet friendly
5.0 out of 5, Exceptional, 227 reviews
Property amenities
Policies
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
Safety features at this property include a fire extinguisher and a first aid kit
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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
- This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, and a first aid kit in each accommodation.
Frequently asked questions
Cheerful 3-Bedroom House in Downtown Annapolis Reviews
Reviews
10
Exceptional
10/10
Cleanliness
Reviews
May 18, 2025
Liked: Cleanliness
Stayed 4 nights in May 2025
10/10 Excellent
Jackie C.
Apr 22, 2025
Liked: Cleanliness
Great location, quiet neighborhood
Jackie C.
Stayed 4 nights in Apr 2025
10/10 Excellent
Anthony T.
Mar 14, 2025
Liked: Cleanliness
Getaway in Annapolis
Anthony T.
Stayed 7 nights in Mar 2025
10/10 Excellent
Curt w.
Jan 18, 2025
Liked: Cleanliness
Very nice!
Curt w.
Stayed 4 nights in Dec 2024
10/10 Excellent
Jan G.
Oct 21, 2024
Liked: Cleanliness
Cozy charm
Jan G.
Stayed 3 nights in Oct 2024
10/10 Excellent
Brian E.
Oct 14, 2024
Liked: Cleanliness
Great home in Annapolis to stay
Brian E.
Stayed 4 nights in Oct 2024
10/10 Excellent
Rob S., Hoover, AL
Sep 11, 2024
Liked: Cleanliness
Great place near historic Annapolis
Rob S.
Stayed 4 nights in Sep 2024
10/10 Excellent
David F.
Jul 1, 2024
Liked: Cleanliness
Clean nice small house. Walking distance to the ocean.
David F.
Stayed 4 nights in Jun 2024
10/10 Excellent
Shehla T.
Dec 3, 2023
Liked: Cleanliness
Thanksgiving away from home
Shehla T.
Stayed 4 nights in Nov 2023
10/10 Excellent
Michael B.
Nov 20, 2023
Liked: Cleanliness
Highly Recommended
Michael B.
Stayed 4 nights in Nov 2023
10/10 Excellent
Christopher M., Panama City Beach, FL 32408
Sep 6, 2023
Liked: Cleanliness
Wonderful home! Great host!
Christopher M.
Stayed 4 nights in Aug 2023
10/10 Excellent
Suzanne I.
Sep 5, 2023
Liked: Cleanliness
Clean and quite
Suzanne I.
Stayed 4 nights in Sep 2023
10/10 Excellent
Sissy A.
Aug 5, 2023
Liked: Cleanliness
Cheerful Stay at Cheerful
Sissy A.
Stayed 7 nights in Jul 2023
10/10 Excellent
Somer T.
Jun 23, 2023
Liked: Cleanliness
Lovely home, close to USNA football stadium
Somer T.
Stayed 5 nights in Jun 2023
10/10 Excellent
Brandi K., Grand Junction, CO
Jun 15, 2023
Liked: Cleanliness
Very helpful!
Brandi K.
Stayed 5 nights in Jun 2023
10/10 Excellent
Rhiannon B., Mahaffey
May 21, 2023
Liked: Cleanliness
Clean nice home
Rhiannon B.
Stayed 3 nights in May 2023
10/10 Excellent
Mary D.
Apr 13, 2023
Liked: Cleanliness
Great family spot in Annapolis
Mary D.
Stayed 4 nights in Mar 2023
10/10 Excellent
Marlis J.
Feb 27, 2023
Liked: Cleanliness
Beautiful Vacation Rental in Annapolis
Marlis J.
Stayed 4 nights in Feb 2023
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