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Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

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A two-story brick building with a balcony, American flags, and a stone wall. - Spacious historic home downtown Annapolis Main St. Book for Commissioning Week! (Annapolis)
A room with a red wall, a wooden dresser, a white staircase, and a door with a window. - Spacious historic home downtown Annapolis Main St. Book for Commissioning Week! (Annapolis)
A neatly made bed with a tufted bench, two bedside tables with lamps, and windows with blinds. - Spacious historic home downtown Annapolis Main St. Book for Commissioning Week! (Annapolis)
A kitchen with white cabinets, stainless steel appliances, a blue tiled floor, and a bar area with stools. - Spacious historic home downtown Annapolis Main St. Book for Commissioning Week! (Annapolis)
A dining table set for four with plates, cutlery, glasses, and a fruit bowl. - Spacious historic home downtown Annapolis Main St. Book for Commissioning Week! (Annapolis)
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

9.2 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)
  • Fire extinguisher
  • Deadbolt lock

General

  • Garden
  • Local artist showcase
  • Recycling
  • Some LED lighting used
  • Unit size: 3,800 square feet
  • Water dispenser

Similar properties

Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age: 18

Check-out

Check-out before 11:00 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

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
View more Vacation homes in Annapolis
Map
Annapolis, MD

What's nearby

  • A white building with a dome, surrounded by lush greenery and a well-maintained garden with pathways and benches.
    William Paca House
    5 min walk - 0.4 km
  • A statue on a pedestal labeled "DEKALB" in front of a brick building with a clock tower.
    Maryland State House
    5 min walk - 0.4 km
  • A grand hall with ornate columns, a large staircase, and flags.
    U.S. Naval Academy
    5 min walk - 0.4 km
  • Annapolis City Dock
    3 min walk - 0.3 km
  • St. John's College
    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
  • Starbucks
    2 min walk
  • The Red Bean
    5 min walk
  • McGarvey's Saloon & Oyster Bar
    3 min walk
  • Chick & Ruth's Delly
    4 min walk

Frequently asked questions

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