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/games room. Free in-room WiFi and laundry facilities are available to all guests.
Reviews
9.49.4 out of 10
Exceptional
Popular amenities
Kitchen
Washing machine
Dryer
Pet-friendly
Free Wi-Fi
Air-conditioning
The current price is NZ$3,240
NZ$3,240
includes taxes & fees
2 Nov - 3 Nov
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 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!
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) with a maximum weight of up to 453 kg per pet.
How much does it cost to stay at Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!?
As of 26 Oct 2026, prices found for a 1-night stay for 2 adults at Spacious historic home downtown Annapolis Main St. Book for Commissioning Week! on 2 Nov 2026 start from NZ$3,240, 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 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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Reviews
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week! Reviews
9.4
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.More informationOpens in a new window
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!
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
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/ 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!
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!
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 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 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!!
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.
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!
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.
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!
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
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.