Entire home
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
Holiday home with kitchen, 9-minute walk to U.S. Naval Academy
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Nestled in Historic Downtown Annapolis, The Oaks Inn combines timeless charm with luxury furnishings and bedding. Ideally situated steps from City Dock, this property offers six bedrooms each with a King or Queen bed and one two-bedroom suite with King and Queen beds. Enjoy the vibrant energy of downtown while relishing comfort on the private balcony or rooftop deck.
Reviews
9.4 out of 10
Exceptional
Entire home
6 bedrooms5 bathroomsSleeps 16353 sq m
Popular amenities
The current price is AU$1,920
includes taxes & fees
26 Jan - 27 Jan 2026
Add dates for prices
About this property
Property amenities
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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
Parties and events (including family gatherings, birthday parties and weddings) are allowed on site. Maximum attendees: 99
Note from host: Other fees may occur for commissioning week/events
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 and a deadlock
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
We should mention
This property does not have any lifts
About the area

Annapolis, MD
Frequently asked questions
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Spacious historic home downtown Annapolis Main St. Book for Commissioning Week! Reviews
Reviews
Exceptional
All reviews shown are from real guest experiences. Only travellers 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.
More informationOpens in a new window9.4
Cleanliness
10
Location
Reviews
31 Aug 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 2 nights in Aug 2025
10/10 Excellent
Michelle R.
30 Sept 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Michelle R.
Stayed 4 nights in Sep 2025
10/10 Excellent
Rachel M.
8 Sept 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Rachel M.
Stayed 2 nights in Sep 2025
8/10 Good
Kerry G.
2 June 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Annapolis Girls Weekend!
Kerry G.
Stayed 2 nights in May 2025
10/10 Excellent
Meg H.
23 June 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great girls trip getaway
Meg H.
Stayed 1 night in Jun 2025
10/10 Excellent
Amy R.
28 Dec 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent location, historic charm, and welcoming hosts
Amy R.
Stayed 7 nights in Dec 2024
10/10 Excellent
Dawn Y.
9 July 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
I-Day send off
Dawn Y.
Stayed 3 nights in Jun 2025
10/10 Excellent
Kristina M.
18 Nov 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful historic home
Kristina M.
Stayed 3 nights in Nov 2024
10/10 Excellent
Leighton S.
21 Apr 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Weekend stay in Annapolis
Leighton S.
Stayed 3 nights in Apr 2024
10/10 Excellent
Ryan M.
18 Aug 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Annapolis home
Ryan M.
Stayed 2 nights in Aug 2024
10/10 Excellent
Adria E.
15 Oct 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect location with a huge yard
Adria E.
Stayed 4 nights in Oct 2024
10/10 Excellent
Elizabeth B.
15 Dec 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Army-Navy Weekend
Elizabeth B.
Stayed 2 nights in Dec 2024
10/10 Excellent
Andrew H.
27 Aug 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect Stay All Around
Andrew H.
Stayed 2 nights in Aug 2024
4/10 Poor
Todd C.
22 June 2025
Liked: Location
Disliked: Cleanliness, check-in, communication, listing accuracy
Very disappointing stay
Todd C.
Stayed 3 nights in Jun 2025
8/10 Good
Kristine F.
11 Sept 2025
Kristine F.
Stayed 2 nights in Aug 2025








