[See all properties](http://www.expedia.ca/Hotel-Search?regionId=&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire home # NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St. Vacation home with kitchen, a short 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) ![Dining](https://images.trvl-media.com/lodging/102000000/101200000/101190100/101190049/3ae18228.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Smart TV, books, stereo](https://images.trvl-media.com/lodging/102000000/101200000/101190100/101190049/w2058h1525x0y1-500a7afd.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) - Overview - Amenities - Policies - Location 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 - Dryer - Barbecue grill - Outdoor space - Pet-friendly ## 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. ### NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St. The Oaks Inn is an exceptional well-kept home, nestled in the heart of Historic Downtown Annapolis, that seamlessly combines timeless historic charm and original wood floors 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 back patio provides an enchanting oasis for relaxing fun. The space The Oaks Inn Annapolis is an immaculate 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 family bedroom with two double beds and a queen bedroom separated by a bathroom. 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 inside the charming portico into the charming sitting room which leads to the dining area and living room, 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 ### 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 - 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 - 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 ![Terrace/patio](https://images.trvl-media.com/lodging/94000000/93510000/93509500/93509468/462b05f1.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### USNA Getaway: Heated Pool, Hot Tub, Indoor Grill! 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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 Located in Historic District, a neighborhood in Annapolis, this vacation 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, motor 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](https://www.expedia.ca/Annapolis.dx6034082) [View more Vacation homes in Annapolis](https://www.expedia.ca/Annapolis-Private-Vacation-Homes.d6034082-aaPrivateVacationHomes.Travel-Guide-Accommodation) ![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 - Maryland State House - 5 min walk - 0.4 km - Annapolis Maritime Museum - 17 min walk - 1.5 km - Navy-Marine Corps Memorial Stadium - 3 min drive - 2.5 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 - ‪O'Brien's Oyster Bar & Seafood Tavern - ‬2 min walk - ‪McGarvey's Saloon & Oyster Bar - ‬3 min walk - ‪Annapolis Market House - ‬3 min walk ## Frequently asked questions ### Is NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St. pet-friendly? > Yes, this property allows dogs (limit 1 total). ### How much does it cost to stay at NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.? > As of Oct 7, 2025, prices found for a 1-night stay for 2 adults at NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St. on Oct 22, 2025 start from CA $978.87, 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 NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.? > Check-in begins at 4:00 PM. ### What time is check-out at NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.? > Check-out is at 11:30 AM. ### Where is NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St. 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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