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

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

Reviews

9.4 out of 10
Exceptional

Highlights

  • Room to spread out
    Enjoy spacious layout that give everyone more room to relax.
  • Beach equipment
    A rare find — beach equipment ready to go for your days by the sea.
  • At the centre of it all
    Stay in a top rated central location, steps from the best attractions, dining, and entertainment.
  • Discover nearby landmarks
    Walk to Maryland State House

Popular amenities

  • Balcony
  • Dog-friendly
  • Barbecue
  • Arcade/game room
  • Breakfast for a fee
  • Air-conditioning

Explore the area

View 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

Rooms & beds

6 bedrooms (sleeps 16)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed and 1 Queen Bed

Bedroom 3

1 Queen Bed

Bedroom 4

1 Queen Bed

Bedroom 5

1 Queen Bed

Bedroom 6

2 Double Beds

Office 1

2 Single Beds

4 bathrooms, 1 half bathroom

Bathroom 1

Soap · Towels provided · Bathtub or shower · Jetted bathtub · Shampoo · Hair dryer

Bathroom 2

Soap · Towels provided · Bathtub or shower · Toilet · Jetted bathtub · Shampoo · Hair dryer

Bathroom 3

Soap · Towels provided · Bathtub or shower · Toilet · Jetted bathtub · Shampoo · Hair dryer

Bathroom 4

Soap · Towels provided · Bathtub or shower · Jetted bathtub · Shampoo · Hair dryer

Bathroom 5

Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Separate dining area
Garden
Dining area

Add dates for prices

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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.
View more Holiday homes in AnnapolisOpens in a new window
Map
Annapolis, MD

What's nearby

  • Annapolis City Dock - 3 min walk - 0.3 km
  • William Paca House - 5 min walk - 0.4 km
  • Maryland State House - 5 min walk - 0.4 km
  • U.S. Naval Academy - 5 min walk - 0.4 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
  • ‪Iron Rooster - ‬3 min walk
  • ‪McGarvey's Saloon & Oyster Bar - ‬3 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) with a maximum weight of up to 453 kg per pet.

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.

Reviews

9.4

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 23 out of 29 reviews
Rating 8 - Good. 4 out of 29 reviews
Rating 6 - Okay. 0 out of 29 reviews
Rating 4 - Poor. 1 out of 29 reviews
Rating 2 - Terrible. 1 out of 29 reviews

9.2/10

Cleanliness

9.4/10

Check-in

9.4/10

Communication

10/10

Location

9.6/10

Listing accuracy

Reviews

Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location
Stayed 2 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
An excellent property in an amazing location. The outdoor space is unheard of in Annapolis. Don't not sleep in the property, just book it! Great communication with the hosts.
Stayed 3 nights in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, communication, location, listing accuracy
Great location, clean house, great service
Stayed 1 night in Apr 2026
Response from VrboOwner on 1 May 2026
Thank you so much for staying at The Oaks Inn Annapolis! You are welcomed back anytime!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
Our group really enjoyed the large outdoor area on the side of the house. We were part of a larger group in town for a wedding and we were able to host a get together for a fairly large group. Over all the house was very comfortable with a great location near heart of Annapolis.
Stayed 2 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place, excellent location!
Stayed 2 nights in Aug 2025
Response from VrboOwner on 1 Sept 2025
If we could leave above a Five Star rating, we would! Joseph and his guests were absolutely wonderful to host. They took great care of our special place and followed all the check-out instructions provided. We welcome you all back anytime! Thank you!
Verified review

10/10 Excellent

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

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
Response from VrboOwner on 21 May 2026
Thank you so much for choosing The Oaks Inn Annapolis! We welcome you back anytime.
Verified review

10/10 Excellent

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
Response from VrboOwner on 16 Dec 2025
Thanks so much!
Verified review

10/10 Excellent

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

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

10/10 Excellent

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
Response from VrboOwner on 8 July 2026
Thanks so much! You are welcomed anytime!
Verified review

8/10 Good

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

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

10/10 Excellent

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
Response from VrboOwner on 1 Sept 2025
Thanks so much for spending time at The Oaks Inn Annapolis. We hope to see you again during the holidays!
Verified review

8/10 Good

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
Response from VrboOwner on 2 June 2025
Glad you enjoyed!
Verified review

10/10 Excellent

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
Response from VrboOwner on 22 Apr 2024
Thank you so much for choosing The Oaks Inn Annapolis! I appreciate your comments; yes, being 1/2 block to Main Street is super fun and convenient to everything!
Verified review

10/10 Excellent

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
Response from VrboOwner on 4 Jan 2025
Thank you for choosing The Oaks! We look forward to seeing you again!
Verified review

10/10 Excellent

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
Response from VrboOwner on 15 Oct 2024
Thank you for choosing The Oaks Inn Annapolis!
Verified review

2/10 Terrible

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
Response from VrboOwner on 1 May 2026
I am absolutely appalled at this review. These fake photos do not depict our beautiful, historic home. Literally NO ONE has ever written such a fake review filled with such vile outrageous falsehoods. You should be ashamed of yourself. The reason VRBO has been unresponsive is because you are lying.
Verified review

10/10 Excellent

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
Response from VrboOwner on 17 Oct 2024
Thanks so much for choosing The Oaks! You all were great guests to host. Looking forward to seeing you again next year!
Verified review

10/10 Excellent

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
Response from VrboOwner on 15 Oct 2024
Thank you so much! Really appreciate you choosing The Oaks Inn Annapolis! #oaksbnb
Verified review

10/10 Excellent

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

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
Response from VrboOwner on 29 June 2025
Thank you so much for your heart-felt review. You are welcome back anytime.
Verified review

10/10 Excellent

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
Response from VrboOwner on 4 Jan 2025
Thanks so much for choosing The Oaks. Looking forward to seeing you again!
Verified review

10/10 Excellent

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
Response from VrboOwner on 10 July 2025
Thank you for your review! You were excellent guests to have and you and your entire family really took care of our historic home. Remember you can just rent a room or two at the USNA rate when you come visit your Mid!😉
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