Title: Spacious historic home downtown Annapolis Main St. Book for Commissioning Week! - Latest Reviews, Deals & Photos 2025 - Expedia.ca [See all properties](http://www.expedia.ca/Hotel-Search?regionId=&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire home # Spacious historic home downtown Annapolis Main St. Book for Commissioning Week! Vacation home with kitchen, 9-minute walk to U.S. Naval Academy ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101200000/101190100/101190049/w1646h1094x1y0-5465a8de.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Exterior](https://images.trvl-media.com/lodging/102000000/101200000/101190100/101190049/w1296h1091x4y3-c34e5260.jpg?impolicy=resizecrop&rw=297&ra=fit) ![6 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/102000000/101200000/101190100/101190049/7087bd89.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Dining](https://images.trvl-media.com/lodging/102000000/101200000/101190100/101190049/576585f9.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Property grounds](https://images.trvl-media.com/lodging/102000000/101200000/101190100/101190049/e06a0d18.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Location - Amenities - Policies 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. 9.4 Exceptional ### Entire home 6 bedrooms5 bathroomsSleeps 163800 sq ft ## Popular amenities - Washer - Kitchen - Fireplace - Dryer - Barbecue grill - Outdoor space ## Add dates for prices Check-in Check-out Travellers ## 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 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 - 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 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 - 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 ## Similar properties ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99230000/99230000/99229951/5203d265.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA Historic District - Kitchen - Washer - Dryer - Free WiFi 10 Exceptional 33 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-12-05&endDate=2025-12-06&selected=99229951&PinnedHotelID=99229951&HadPinnedHotel=true®ionId=-1&adults=2) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89690000/89688000/89687951/a3cb6bf6.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Stunning, Large Historic Annapolis Home, Steps to Downtown, Private Driveway! 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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 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: 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 ## About the area ![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6&zoom=13&markers=icon:https%3A%2F%2Fa.travel-assets.com%2Ftravel-assets-manager%2Feg-maps%2Fproperty.png%7C38.97647%2C-76.48831&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=g-_B3VfZ8ju-Qb07INHgFzoLNAQ=) Annapolis, MD #### What's nearby - Annapolis City Dock - 3 min walk - 0.3 km - U.S. Naval Academy - 3 min walk - 0.3 km - William Paca House - 5 min walk - 0.4 km - Maryland State House - 5 min walk - 0.4 km - Thurgood Marshall Memorial - 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 - ‪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 ## 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). ### How much does it cost to stay at Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!? > As of Nov 21, 2025, prices found for a 1-night stay for 2 adults at Spacious historic home downtown Annapolis Main St. Book for Commissioning Week! on Nov 25, 2025 start from CA $887.36, excluding 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](https://www.expedia.ca/Annapolis-Hotels-Grand.h101190049.Hotel-Information?rfrr=HOT.HIS.question.link.click) for more accurate prices. ### 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!? > Check-out is at 11:30 AM. ### Where is Spacious historic home downtown Annapolis Main St. Book for Commissioning Week! located? > Located in Historic District, this vacation 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. ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. 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