Entire home
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
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Reviews
9.49.4 out of 10
Exceptional
Entire home
6 bedrooms5 bathroomsSleeps 16353 sq m
Popular amenities
- Barbecue grill
- Washer
- Fireplace
- Dryer
- Kitchen
- Pet-friendly
Explore the area

Annapolis, MD
- Annapolis City DockPlace, Annapolis City Dock3 min walk
- U.S. Naval AcademyPlace, U.S. Naval Academy3 min walk
- Maryland State HousePlace, Maryland State House5 min walk
- Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)32 min drive
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About the area
Annapolis
This vacation home is in the heart of Annapolis, within a 10-minute walk of Maynard-Burgess House and U.S. Naval Academy. .This vacation home is 0.1 mi (0.2 km) from Kunta Kinte Plaque & Alex Haley Memorial and 0.1 mi (0.2 km) from Annapolis Harbor.
What's nearby
- Annapolis City Dock - 3 min walk - 0.3 km
- U.S. Naval Academy - 3 min walk - 0.3 km
- William Paca House - 5 min walk - 0.4 km
- Maryland State House - 5 min walk - 0.4 km
- Thurgood Marshall Memorial - 6 min walk - 0.6 km
Getting around
- Odenton Station - 22 min drive
- Fort Meade, MD (FME-Tipton) - 31 min drive
Restaurants
- The Choptank - 3 min walk
- O'Brien's Oyster Bar & Seafood Tavern - 2 min walk
- Annapolis Market House - 3 min walk
- McGarvey's Saloon & Oyster Bar - 3 min walk
- Starbucks - 2 min walk
About this property
Entire place
You'll have the entire home to yourself and will only share it with other guests in your party.
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!
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!
Make yourself comfortable in this air-conditioned vacation home, which features a fireplace and a Smart TV. There's a private balcony. A kitchen is outfitted with a refrigerator, an oven, and a stovetop. Complimentary wireless internet access is available to keep you connected. The bathroom has a jetted bathtub and a hair dryer.
Take in the views from a garden and make use of amenities such as concierge services and an arcade/game room.
Breakfast is available for a fee.
Featured amenities include laundry facilities and a water dispenser.
Property amenities
Beach
- Beach loungers
- Beach towels
Internet
- Available in the house: Free WiFi
Parking and transport
- No on-site parking available
Kitchen
- Coffee/tea maker
- Cookware, dishware, and utensils
- Dishwasher
- Electric kettle
- Hob
- Ice maker
- Kitchen island
- Microwave
- Oven
- Paper towels
- Refrigerator
- Spices
- 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
- Living room
- 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 lift
- Smoke-free property
Services and conveniences
- Concierge services
- Iron/ironing board
- Meal delivery service
Location highlights
- In the city centre
- 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)
- Fire extinguisher
- Deadbolt lock
General
- At least 10% of profits reinvested in community and sustainability
- At least 80% lighting from LEDs
- Energy-saving switches in guestrooms
- Garden
- Local artist showcase
- Recycling
- Unit size: 3,800 square feet
- Water dispenser
Policies
Check-in
Check-in time starts at 4:00 PM
Minimum check-in age: 18
Check-out
Check-out before 11:30 AM
Special check-in instructions
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
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
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 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