Photo gallery for NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.





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 bedrooms 5 bathrooms Sleeps 16 3800 sq ft
Popular amenities
The current price is £1,332
includes taxes & fees
22 Sept - 23 Sept
Add dates for prices
About this property
Property amenities
Policies
Important information
You need to know
This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.
About the area
Located in Historic District, a neighbourhood in Annapolis, this holiday home is near theme parks. Annapolis Harbor and Ego Alley are worth checking out if an activity is on the agenda, while those in the mood for shopping can visit Annapolis City Dock and Bay Bridge Market Place Shopping Center. French Soldiers Monument and Annapolis Maritime Museum are also worth visiting. Kayaking, power boating and sailing offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling nearby.

Annapolis, MD
What's nearby
- Annapolis City Dock - 3 min walk - 0.2 miles
- U.S. Naval Academy - 3 min walk - 0.2 miles
- Maryland State House - 5 min walk - 0.3 miles
- Annapolis Maritime Museum - 17 min walk - 0.9 miles
- Navy-Marine Corps Memorial Stadium - 3 min drive - 1.6 miles
Getting around
Restaurants
- Starbucks - 2 min walk
- The Choptank - 3 min walk
- Chick & Ruth's Delly - 4 min walk
- Mc Garvey's Saloon - 3 min walk
- Federal House - 2 min walk
Frequently asked questions
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NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St. Reviews
Reviews
9.4
Exceptional
9.4/10
Cleanliness
Reviews
28 Dec 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 7 nights in Dec 2024
8/10 Good
Kerry G.
2 Jun 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Annapolis Girls Weekend!
Kerry G.
Stayed 2 nights in May 2025
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
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
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