Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
The Oaks Inn is a well-kept home, built in 1930 with original hardwood floors. It is nestled in the heart of Historic Downtown Annapolis and seamlessly combines timeless historic charm and original architecture with upscale furnishings and bedding. Ideally situated steps from City Dock, US Naval Academy, and the bustling ambiance of Main St., this property is also a short walk to the State Capitol. Enjoy the vibrant energy while relishing the comfort and privacy of a quaint street. The Oaks House Inn Annapolis boasts both charm and ambiance and serves as the perfect location for dining and entertaining. The spacious brick back patio provides an enchanting oasis for relaxing fun. And the lawn area is perfect for outdoor games. There is an outdoor grill, heat lamps and a firepit for your outside enjoyment.
The space The Oaks Inn Annapolis is a beautiful property. Guests are presented an extraordinary opportunity to stay in one of the six bedrooms each with a King or Queen bed, one two-bedroom suite with King and Queen beds, and one suite with two double beds and a furnished rooftop deck. This location offers the epitome of convenient city adventure. Enjoy the best of both worlds with easy access to the vibrant energy of downtown Annapolis while still relishing the comfort and privacy of a quaint residential street. Step through the charming portico into back yard and side door that leads to the charming sitting room, dining area and living room to the right and game/tv room, kitchen and bar lounge area to the left. The home is thoughtfully designed to foster a harmonious flow between living spaces. The family game room and back lounge space with a bar and easy access to the spacious brick patio, garden and firepit area, serve as wonderful gathering places for entertaining guests, friends and family. On the 2nd floor, you'll find three nicely-sized bedroom suites with two full bathrooms, and one with a private balcony exuding a warm and inviting relaxed place to chill. Continue to the third floor, where three additional private bedroom suites with 2 full bathrooms await, one of which offers a rooftop deck amongst the tree tops. The fourth floor leads you to a spacious loft perfect for quiet reading, working or kids play-space. Not to be overlooked, the back patio provides an enchanting oasis for hosting gatherings, grilling, or simply relaxing amidst the beautiful surroundings. Don't miss the opportunity to visit, stay and play in the historic Oaks Inn Annapolis, as it combines the essence of Annapolis' rich history with modern elegance in one of Maryland's most coveted locations. Please note: summer A/C and CW fee applies!
Our prices include all fees. No hidden fees.
Add dates for prices
Have a question?
AI iconBetaBeta
Get instant answers with AI powered search of property information and reviews.
Similar properties
Brilliantly Updated Multi-Level Walkable to Navy Stadium & Close to Historic Downtown Annapolis
Admiral Heights
Brilliantly Updated Multi-Level Walkable to Navy Stadium & Close to Historic Downtown Annapolis
Events allowed: family gatherings, birthday parties, weddings
Other fees occur for commissioning week and events
default
Pets
Pets allowed: dogs (limit 1 total)
Dogs not allowed in carpeted bedrooms
default
Smoking
Smoking is not permitted
Check-out instructions
The host requires you to complete the following before checking out:
Load and start the dishwasher
Strip any used beds and gather used towels
Remove personal items, remove leftover food and drinks and take out the rubbish
Turn off the lights and lock the doors
Turn off AC units
Put any indoor or outdoor furniture that has been moved back to how it was found. (In its original place.)
Put used towels in laundry room.
Failure to complete these may result in a negative review from the host.
1. Event fees occur for gatherings that involve outside guests. Refer to event guide
2. 2-night min during holidays
1. Do not light fireplace or candles inside.
2. All furniture/objects moved need to be put how you found it
3. 5 day minimum during CW and fee added
1.Take trash to garbage can outside- take to curb on Sundays
2. Remove sheets; leave at the end of the bed
3. Close windows/curtains at check-out
Important information
You need to know
Property # 3772255vb
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.
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: 80
Note from host: Other fees occur for commissioning week and 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
About the area
Annapolis
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.
Is Spacious historic home downtown Annapolis Main St. Book for Commissioning Week! pet-friendly?
Yes, this property allows dogs (limit 1 total).
How much does it cost to stay at Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!?
As of 22 Aug 2026, prices found for a 1-night stay for 2 adults at Spacious historic home downtown Annapolis Main St. Book for Commissioning Week! on 7 Dec 2026 start from £1,123, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
How much is parking at Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!?
This property doesn't offer parking.
What time is check-in at Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!?
Check-in begins at 4:00 PM.
What time is check-out at Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!?
Checkout is at 11:00 AM.
Where is Spacious historic home downtown Annapolis Main St. Book for Commissioning Week! located?
Located in Historic District, this holiday home is within a 5-minute walk of Maynard-Burgess House and Annapolis City Dock. Annapolis Harbor and 14 Fleet Street are also within 5 minutes.
About the host
Hosted by Sharon and Quinton Wilder
Why they chose this property
Fun town; great restaurants and nightlife; nearby sailing and boating.
What makes this property unique
This immaculate Inn presents an extraordinary opportunity to stay in a historic property that seamlessly combines timeless historic charm and original wood floors with modern luxury furnishings and bedding. Ideally situated just a short stroll away from renowned landmarks such as the Naval Academy and City Dock, as well as the bustling ambiance of Main Street, State Circle and Maryland Avenue, this location offers the epitome of convenient city adventure. Enjoy the best of both worlds with easy access to the vibrant energy of downtown Annapolis while still relishing the comfort and privacy of a quaint residential street.
Step inside the charming portico into the game room which leads to a chef’s kitchen and back bar, thoughtfully designed to foster a harmonious flow between living spaces. The living room and dining room boasts charm and ambiance, and serve as the perfect centerpiece for entertaining guests, friends and family. Events are permitted with additional fees.
Languages:
English
Premier Host
They consistently provide great experiences for their guests