Located close to Annapolis City Dock and U.S. Naval Academy, Spacious historic home downtown Annapolis Main St. Book for Commissioning Week! provides a firepit, a garden, and an arcade/game room. Free in-room WiFi and laundry facilities are available to all guests.
Reviews
9.29.2 out of 10
Wonderful
Entire home
6 bedrooms5 bathroomsSleeps 163800 sq ft
Popular amenities
Kitchen
Washer
Dryer
Pet friendly
Free WiFi
Air conditioning
Add dates for prices
About this property
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!
Property amenities
Beach
Beach loungers
Beach towels
Internet
Available in the house: Free WiFi
Parking and transportation
No onsite parking available
Kitchen
Coffee/tea maker
Cookware, dishware, and utensils
Dishwasher
Electric kettle
Ice maker
Kitchen island
Microwave
Oven
Paper towels
Refrigerator
Spices
Stovetop
Toaster
Water dispenser
Dining
Breakfast available for a fee
Chef service
Dining table
Bedrooms
6 bedrooms
Bedsheets provided
Bathroom
4.5 bathrooms
Bathtub or shower
Hair dryer
Jetted bathtub
Shampoo
Soap
Toilet paper
Towels provided
Living spaces
Dining table
Fireplace
Separate dining area
Entertainment
Books
Games
Smart TV with cable/satellite channels
Stereo
Outdoor areas
Balcony
Barbecue grill
Firepit
Garden
Outdoor furniture
Laundry
Laundry facilities
Washing machine
Work spaces
Desk
Desk chair
Comfort
Air conditioning
Heating
Pets
Pet friendly
Welcoming dogs only
One pet total
Suitability/Accessibility
No elevator
Smoking not allowed
Services and conveniences
Concierge services
Iron/ironing board
Meal delivery service
Location highlights
In the city center
Near a health/beauty spa
Near a hospital
Near the bay
Near the marina
Things to do
Arcade/game room
Basketball nearby
Cycling nearby
Fishing nearby
Golfing nearby
Kayaking nearby
Motor boating nearby
Sailing nearby
Theme park nearby
Safety features
Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
Smoke detector (host has indicated there is a smoke detector on the property)
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools
Check-out instructions
The host requires you 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 trash
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.
Rules
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
Pets
Pets allowed
Service animals are welcome, and are exempt from fees
Welcoming dogs only
1 total pets
Note from host: Dogs not allowed in carpeted bedrooms
Children and extra beds
Children are welcome
Events
Events allowed: family gatherings, birthday parties, weddings
Other fees occur for commissioning week and events
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
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 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 deadbolt lock
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 elevators
About the area
Located in Historic District, a neighborhood in Annapolis, this vacation 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, motor boating, and sailing offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling nearby. Visit our Annapolis travel guide
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 Sept 2, 2026, prices found for a 1-night stay for 2 adults at Spacious historic home downtown Annapolis Main St. Book for Commissioning Week! on Sept 8, 2026 start from CA $1,247, excluding 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?
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!?
Check-out is at 11:00 AM.
Where is Spacious historic home downtown Annapolis Main St. Book for Commissioning Week! located?
Located in Historic District, this vacation 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.
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Spacious historic home downtown Annapolis Main St. Book for Commissioning Week! Reviews