Nestled in Historic Downtown Annapolis, The Oaks Inn combines timeless charm with luxury furnishings and bedding. Ideally situated steps from City Dock, this property offers six bedrooms each with a King or Queen bed and one two-bedroom suite with King and Queen beds. Enjoy the vibrant energy of downtown while relishing comfort on the private balcony or rooftop deck.
Reviews
9.49.4 out of 10
Exceptional
Entire home
6 bedrooms5 bathroomsSleeps 16353 sq m
Popular amenities
Kitchen
Washing machine
Dryer
Pet-friendly
Free Wi-Fi
Air-conditioning
The current price is NZ$2,351
NZ$2,351
includes taxes & fees
10 Mar - 11 Mar
Add dates for prices
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!
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
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
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
Pets are 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 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: 80
Note from host: Other fees may occur for commissioning week/events
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock
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 any lifts
About the area
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. Visit our Annapolis travel guide
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 9 Mar 2026, prices found for a 1-night stay for 2 adults at Spacious historic home downtown Annapolis Main St. Book for Commissioning Week! on 10 Mar 2026 start from NZ$2,351, 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.
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 10-minute walk of Maynard-Burgess House and U.S. Naval Academy. 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
Reviews
Exceptional
All reviews shown are from real guest experiences. Only travellers 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.
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.
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
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!
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!
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
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.
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!
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.
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!!
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!
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.
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.