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

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

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

Reviews

9.4 out of 10
Exceptional

Entire home

6 bedrooms5 bathroomsSleeps 163800 sq ft

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
  • Free WiFi
  • Air conditioning

Explore the area

View in a map
Annapolis, MD
  • Place, Annapolis City Dock
    ‪3 min walk‬
  • Place, Maryland State House
    ‪5 min walk‬
  • Place, U.S. Naval Academy
    ‪5 min walk‬
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪38 min drive‬

Room options

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About the neighborhood

Annapolis

Located in Historic District, this vacation home is within a 5-minute walk of Annapolis City Dock and within 15 minutes of other popular attractions like U.S. Naval Academy. The vacation home includes a kitchen, a fireplace, and a balcony.
View more Vacation Homes in AnnapolisOpens in a new window

What's nearby

  • Annapolis City Dock - 3 min walk - 0.2 miles
  • William Paca House - 5 min walk - 0.3 miles
  • Maryland State House - 5 min walk - 0.3 miles
  • U.S. Naval Academy - 5 min walk - 0.3 miles
  • St. John's College - 6 min walk - 0.4 miles

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
  • ‪Iron Rooster - ‬3 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 1860 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 vacation home is air-conditioned and features a kitchen, 4.5 bathrooms, and a balcony. There's space to spread out with 6 bedrooms and a dining area. Guests can enjoy a Smart TV and stay connected with free WiFi. The bathroom offers a jetted tub and hair dryers. Other standard amenities include a washing machine, a fireplace, and a coffee maker.

Similar properties

Meeting facility
Historic Inns of Annapolis
Historic District
  • Pet friendly
  • Free WiFi
  • Restaurant
  • Air conditioning
9.0 out of 10, 1999, 1,999 reviews
$140 nightly
The price is $159
Oct 12 - Oct 13
Total with taxes and fees
Historic Inns of Annapolis

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

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

  • This property welcomes pets
  • Dogs only
  • 1 total pets
  • Service animals exempt from fees
  • Note from host: Dogs not allowed in carpeted bedrooms

Children and extra beds

Children allowed: ages 0-17

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
  • Check-in: 4:00 PM
  • Check-out: 11:00 AM
  • Minimum check-in age: 18

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • No parking is available onsite.
  • 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
  • Onsite safety features include a carbon monoxide detector, a fire extinguisher, a smoke detector, and a deadbolt lock.

Additional information about polices, regulations, and more:

  • There are no elevators.

Frequently asked questions

What's there to see around this vacation home?

This vacation home is situated in Historic District, just steps from Annapolis City Dock and Maynard-Burgess House, and within a short walk of Maryland State House. You'll also find William Paca House and Annapolis Harbor less than a mile away.

How much does it cost to stay at Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!?

As of Sep 14, 2026, prices found for a 1-night stay for 2 adults at Spacious historic home downtown Annapolis Main St. Book for Commissioning Week! on Sep 15, 2026 start from $2,107, 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.

Is this vacation home next to a casino?

No, this vacation home is not connected to a casino.

Will I find an indoor pool at this vacation home?

No, there is no indoor pool at this vacation home.

Does this vacation home provide breakfast?

This vacation home offers breakfast for a surcharge.

Will this vacation home allow pets to stay free of charge?

Although dogs can't stay for free, they are welcome at this vacation home.

Where is the closest airport to this vacation home?

The closest major airport to this vacation home is Fort Meade, MD (FME-Tipton), which is 21.1 mi away (31 minutes by car). Another top airport is Baltimore Washington Intl. Airport (BWI), which is located 29.3 mi away (40-minute drive).

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

Reviews

9.4

Exceptional

Rating 10 - Excellent. 22 out of 28 reviews
Rating 8 - Good. 4 out of 28 reviews
Rating 6 - Okay. 0 out of 28 reviews
Rating 4 - Poor. 1 out of 28 reviews
Rating 2 - Terrible. 1 out of 28 reviews

9.2/10

Cleanliness

Reviews

Verified review

10/10 Excellent

Shamaila U.

Liked: Cleanliness, communication, location, listing accuracy
Great location, clean house, great service
Stayed 1 night in Apr 2026
Verified review

10/10 Excellent

Sabrina A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We rented the entire house for a graduation party for 55 people and 14 guests. The house was sheer perfection. Has a great vibe. Tons of ndoor and outdo seating. And Sandra was there for all our questions. Highly recommend!
Stayed 2 nights in May 2026
Verified review

10/10 Excellent

Joseph C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place, excellent location!
Stayed 2 nights in Aug 2025
Verified review

10/10 Excellent

Lindsey M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
we had a wonderful time! House was beautiful, will definitely be back!
Stayed 1 night in Nov 2025
Verified review

10/10 Excellent

Ward U.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The owners were very good with pre and post-check in communications, and were on site to meet us and show us the property. It was an excellent stay with an excellent location. Kitchen was well stocked and lots of room for everyone.
Stayed 3 nights in Dec 2025
Verified review

10/10 Excellent

Nancy M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This house is in a fabulous location! You can walk everywhere. Parking and unloading is a little tricky but once that is done you don’t need your car anymore. The house has lots of bedrooms for couples or singles. There is plenty of entertaining space inside and out. It’s an older house so room after room! It’s nicely decorated, very homey and lots of amenities. The kitchen was well equipped. Sharon, the host, met us and took us on the house tour. She was very friendly and informative. I highly recommend!
Stayed 2 nights in Jun 2026
Verified review

10/10 Excellent

Brad B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Located a block from the City Dock heart of Annapolis, it was a perfect location for our USNA class reunion! Property is clean and well appointed...great stay!
Stayed 3 nights in Sep 2025
Verified review

10/10 Excellent

Michelle R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very spacious historic property footsteps from downtown. Great yard for hosting big groups and a well attended kitchen.
Stayed 4 nights in Sep 2025
Verified review

8/10 Good

Jeff L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Extremely spacious for my family located close to many Annapolis historic sites, restaurants and shopping. Close to the USNA what we needed. Lots of living and entertainment spaces. The yard is huge, great for gatherings.
Stayed 4 nights in Oct 2025
Verified review

10/10 Excellent

Vicki P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The host was very welcoming and helpful. The house was a perfect location and walk to everything! Many bedrooms, bathrooms, coffee makers, balconies, yard with many places to sit, and easy to find. Perfect for our girls weekend and we all had our own bedrooms
Stayed 1 night in Nov 2025
Verified review

2/10 Terrible

Bruce K.

Liked: Location
Disliked: Cleanliness, check-in, communication, listing accuracy
Host MIA; didn’t reply to text or call; place was like a crack house; filthy; trash had not been removed; no wall unit AC in all bedrooms; online pics 100% deceptive; VRBO contacted and have been unresponsive
Stayed 3 nights in Apr 2026
Verified review

10/10 Excellent

Amy R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent location, historic charm, and welcoming hosts

Three generations of family gathered here for a holiday together. The beautiful historic home is located in the heart of downtown Annapolis - activities for everyone within blocks. We opted for the chef-prepared breakfast,- a highlight!
Stayed 7 nights in Dec 2024
Verified review

8/10 Good

Kerry G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Annapolis Girls Weekend!

Our group had a great time! This house was super convenient location and easily walkable to Main Street. Thank you!
Stayed 2 nights in May 2025
Verified review

10/10 Excellent

Leighton S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Weekend stay in Annapolis

Very comfortable home with the proximity to downtown. Loved it!!
Stayed 3 nights in Apr 2024
Verified review

10/10 Excellent

Kristina M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful historic home

Perfect place location and size for my friends and family for our Naval Academy reunion. Thank you!!
Stayed 3 nights in Nov 2024
Verified review

10/10 Excellent

Ryan M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Annapolis home

The house/ Inn is a fantastic location to downtown Annapolis. Parking is very convenient which can at times be hard in Annapolis. The out door space is fantastic. The beds are extremely comfortable and the historic vibe of the house is just very cool.
Stayed 2 nights in Aug 2024
Verified review

10/10 Excellent

Rachel M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The Oaks is in an absolutely perfect location and checks all the boxes a large family needs for a stay. We booked it for our wedding at the AYC for close family and it was far superior to booking 6 hotel rooms where everyone would have been locked in their own rooms. They hung out and spent a great time together on the main level. It was nice to be at a historic home with all the fun quirks. The hosts were responsive and accommodating. Highly recommend!
Stayed 2 nights in Sep 2025
Verified review

10/10 Excellent

Meg H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great girls trip getaway

The house was perfect for our needs. There were lots of bedrooms and communal spaces. The kitchen is fully stocked which was a bonus. You couldn’t ask for a better location, everything is within walking distance. There is even a short cut from the parking garage to the house. Highly recommend this listing
Stayed 1 night in Jun 2025
Verified review

10/10 Excellent

Adria E.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect location with a huge yard

This sprawling house worked perfectly for our group of friends attending the boat show. The location is perfect, just steps from the dock and a very short walk to everything else. We had plenty of space to spread out and enjoyed the huge backyard for grilling and eating outside. Definitely plan to return!
Stayed 4 nights in Oct 2024
Verified review

10/10 Excellent

Andrew H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Stay All Around

This home was perfect in every way. It is located just steps away from downtown Annapolis. The entire house was gorgeous and had an awesome yard to hang out. We had a group of 13 and had plenty of room, easily could have comfortable fit at least a few more.
Stayed 2 nights in Aug 2024
Verified review

10/10 Excellent

Elizabeth B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Army-Navy Weekend

The gigantic house was perfect for our quick Army-Navy Football game weekend. We hope to come back when it’s warm to take advantage of the great gathering spaces outdoors. Go Navy! Beat Army!!
Stayed 2 nights in Dec 2024
Verified review

10/10 Excellent

Dawn Y.

Liked: Cleanliness, check-in, communication, location, listing accuracy

I-Day send off

Our family included ages 18-81! The stairs for bedrooms were a little challenging for the 80 year old, but we knew that going in. We rented an electric scooter for traveling back and forth to USNA. All the different areas for our group of 9 (8 after sending out new midshipman off) were great for accommodating all our different needs.
Stayed 3 nights in Jun 2025
Verified review

4/10 Poor

Todd C.

Liked: Location
Disliked: Cleanliness, check-in, communication, listing accuracy

Very disappointing stay

Extremely disappointed. Began with wrong information about check in time. Followed by one bedroom not having a working air conditioner in 90 degree weather. Another bedroom air conditioner has hose on the ground, my husband went to get duct tape to repair. Repair man did show up to get bedroom working. Food left in refrigerator that was ours to use. Viking oven had a large oven that would not heat up , yet the two smaller oven did heat up. One bedroom had a fly problem. Bought spray, taped around the air conditioner, and the flies were back. Disgusting. Couldn’t use that bedroom for the last night. Let property manger know through text, no response. Every small area rug was filthy, shower curtains need liner replacement. We made the best of it. We loved Annapolis but we would never rent this home again. Also, large yard was spacious but unkept.
Stayed 3 nights in Jun 2025
Verified review

8/10 Good

Kristine F.

Stayed 2 nights in Aug 2025

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