Located in Historic District, this vacation home is next to Maynard-Burgess House and Kunta Kinte Plaque & Alex Haley Memorial. The vacation home includes a kitchen, a fireplace, and a balcony.
Annapolis Maritime Museum - 17 min walk - 0.9 miles
Navy-Marine Corps Memorial Stadium - 3 min drive - 1.6 miles
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
Starbucks - 2 min walk
Annapolis Market House - 3 min walk
McGarvey's Saloon & Oyster Bar - 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 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 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.
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
Rules
2 night min holidays
1. Put towels in laundry
2. Remove sheets and leave them at the end of the bed
3. Wash dishes and/or load and start dishwasher
1. Do not light fireplace or candles inside.
2. All furniture/objects moved need to be put how you found it
5 day minimum during CW plus fee added
1.Take trash to garbage can outside- take to curb if Sunday
2. Turn off lights, fans, and thermostats.
3. Close windows and curtains upon 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 may occur for commissioning week/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: 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
Check-in: 4:00 PM
Check-out: 11:30 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.
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
Onsite safety features include a carbon monoxide detector, a fire extinguisher, a smoke detector, and a deadbolt lock.
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 Ego Alley. You'll also find Maryland State House and William Paca House less than a mile away.
Will I be able to park at this vacation home?
No, there isn't parking available at the vacation home.
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.
Is Spacious historic home downtown Annapolis Main St. Book for Commissioning Week! good for couples?
There are many amenities for couples at this vacation home, including a fireplace and access to a chef in each accommodation with some featuring fireplaces.
Are there hot tubs at Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!?
No, but all accommodations at this vacation home have jetted bathtubs.
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.
Does this vacation home have connecting rooms?
No, there aren't connecting rooms 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).
Are there rooms with balconies at Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!?
Yes, every accommodation at Spacious historic home downtown Annapolis Main St. Book for Commissioning Week! comes with a balcony.
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week! Reviews
Reviews
9.4
Exceptional
All reviews shown are from real guest experiences. Only travelers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
Rating 10 - Excellent. 13 out of 17 reviews
10 - Excellent
13
Rating 8 - Good. 3 out of 17 reviews
8 - Good
3
Rating 6 - Okay. 0 out of 17 reviews
6 - Okay
0
Rating 4 - Poor. 1 out of 17 reviews
4 - Poor
1
Rating 2 - Terrible. 0 out of 17 reviews
2 - Terrible
0
9.2/10
Cleanliness
Reviews
8/10 Good
Jeff L.
Oct 29, 2025
Liked: Cleanliness
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.
Jeff L.
Stayed 4 nights in Oct 2025
10/10 Excellent
Brad B.
Oct 2, 2025
Liked: Cleanliness
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!
Brad B.
Stayed 3 nights in Sep 2025
10/10 Excellent
Michelle R.
Sep 30, 2025
Liked: Cleanliness
Very spacious historic property footsteps from downtown. Great yard for hosting big groups and a well attended kitchen.
Michelle R.
Stayed 4 nights in Sep 2025
8/10 Good
Kristine F.
Sep 11, 2025
Kristine F.
Stayed 2 nights in Aug 2025
10/10 Excellent
Rachel M.
Sep 8, 2025
Liked: Cleanliness
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!
Rachel M.
Stayed 2 nights in Sep 2025
10/10 Excellent
Joseph C.
Aug 31, 2025
Liked: Cleanliness
Great place, excellent location!
Joseph C.
Stayed 2 nights in Aug 2025
10/10 Excellent
Dawn Y., Binghamton, NY
Jul 9, 2025
Liked: Cleanliness
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.
Dawn Y.
Stayed 3 nights in Jun 2025
10/10 Excellent
Meg H.
Jun 23, 2025
Liked: Cleanliness
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
Meg H.
Stayed 1 night in Jun 2025
4/10 Poor
Todd C.
Jun 22, 2025
Disliked: Cleanliness
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.
Todd C.
Stayed 3 nights in Jun 2025
8/10 Good
Kerry G.
Jun 2, 2025
Liked: Cleanliness
Annapolis Girls Weekend!
Our group had a great time! This house was super convenient location and easily walkable to Main Street. Thank you!
Kerry G.
Stayed 2 nights in May 2025
10/10 Excellent
Amy R.
Dec 28, 2024
Liked: Cleanliness
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!
Amy R.
Stayed 7 nights in Dec 2024
10/10 Excellent
Elizabeth B., Milwaukee
Dec 15, 2024
Liked: Cleanliness
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!!
Elizabeth B.
Stayed 2 nights in Dec 2024
10/10 Excellent
Kristina M.
Nov 18, 2024
Liked: Cleanliness
Beautiful historic home
Perfect place location and size for my friends and family for our Naval Academy reunion. Thank you!!
Kristina M.
Stayed 3 nights in Nov 2024
10/10 Excellent
Adria E., Guilderland NY
Oct 15, 2024
Liked: Cleanliness
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!
Adria E.
Stayed 4 nights in Oct 2024
10/10 Excellent
Andrew H.
Aug 27, 2024
Liked: Cleanliness
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.
Andrew H.
Stayed 2 nights in Aug 2024
10/10 Excellent
Ryan M.
Aug 18, 2024
Liked: Cleanliness
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.
Ryan M.
Stayed 2 nights in Aug 2024
10/10 Excellent
Leighton S.
Apr 21, 2024
Liked: Cleanliness
Weekend stay in Annapolis
Very comfortable home with the proximity to downtown. Loved it!!