Spacious historic home downtown Annapolis Main St. Book for Commissioning Week! | House in Annapolis

9.4 (20 Reviews) |   Pet Friendly   6 Bedrooms  4 Bathrooms  16 Guests
Historic District House | Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

6 Bedroom House in Historic District, Annapolis

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!

Spacious historic home downtown Annapolis Main St Book for Commissioning Week! is located in Historic District. Spacious historic home downtown Annapolis Main St Book for Commissioning Week! provides accommodation, featuring Bedding/Linens, Child Friendly, Pet Friendly, among other amenities. This House features Bedding/Linens, Child Friendly, Pet Friendly, to make your stay a comfortable one.

Spacious historic home downtown Annapolis Main St Book for Commissioning Week! has 6 Bedrooms , 4 Bathrooms, and max occupancy of 16 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the Historic District has interesting places to visit. If you want to learn more about the House in Historic District, such as places to visit and things to do nearby, you can check below to learn more.

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Amenities

Air Conditioner
Pet Friendly
TV
View
Ocean View
Balcony/Terrace
Security/Safety
Sports/Activities
Bedding/Linens
Wellness Facilities
Fireplace/Heating
Guest Services
Entertainment
Breakfast
Barbecue/Outdoor Cooking
Child Friendly
Hot Tub
Internet
Kitchen
Laundry

Facility Overview

Air Conditioner
  • Heating
  • Air conditioning
Bathrooms
  • 4+ bathrooms
  • Hair dryer
  • Bathtub or shower
  • Shampoo
  • Toilet paper
  • Jetted bathtub
  • Soap
  • Towels provided
Bedroom
  • 6 bedrooms
  • Bed sheets provided
  • Dining table
  • Breakfast available for a fee
  • Fireplace
  • Dining room
  • Living room
Kitchen
  • Spices
  • Stovetop
  • Refrigerator
  • Coffee/tea maker
  • Ice maker
  • Oven
  • Microwave
  • Water dispenser
  • Dishwasher
Laundry
  • Washing machine and dryer
  • Near laundromat
  • Laundry facilities
Ocean view
  • Beach towels
  • Beach sun loungers
Parking
  • No onsite parking available
Pet Friendly
  • 1 total pets
  • Welcoming dogs only
  • Pet friendly
Accessibility
  • No elevators
  • Smoke-free property
Activities
  • Cycling nearby
  • Theme parks nearby
  • Fitness facilities nearby
  • Golf nearby
  • Kayaking nearby
  • Basketball nearby
  • Sailing nearby
  • Fishing nearby
  • Marina nearby
  • Power boating nearby
Entertainment
  • Stereo
  • Games
  • Smart TV with cable/satellite service
  • Books
  • Arcade/game room
General
  • Energy-saving switches
  • At least 10% of profits reinvested in community & sustainability
  • Recycling
  • Local artist showcase
  • Unit size: 3800 sq ft (353 sq m)
  • At least 80% lighting from LEDs
  • English
  • Near the bay
  • Near a health or beauty spa
  • In the city center
  • Near a hospital
  • Desk
  • Desk chair
Guest Services
  • Iron/ironing board
  • Chef
  • Local meal delivery service
  • Concierge services
Internet
  • Free WiFi
Outdoors
  • Garden
  • Balcony
  • Barbecue grill
  • Firepit
  • Outdoor furniture
Security/Safety
  • Deadbolt lock
  • Smoke detector installed (host has indicated there is a smoke detector on the property)
  • Carbon monoxide detector installed (host has indicated there is a carbon monoxide detector on the property)
  • Fire extinguisher

Policies

Check-in
Check-in time starts at 4:00 pm minimum check-in age: 18
Check-out
Check-out before 11:00 am
Child Policy
Children are welcome.
Event Policy
Events allowed: family gatherings, birthday parties, weddings;maximum event attendees: 99;other fees may occur for commissioning week/events
Pet Policy
1 total pets note from host: dogs not allowed in carpeted bedrooms pets allowed service animals are welcome, and are exempt from fees welcoming dogs only
Smoking Policy
Smoking is not permitted

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 host has indicated there is a carbon monoxide detector on the property host has indicated there is a smoke detector on the property note from host: other fees may occur for commissioning week/events parties and events (including family gatherings, birthday parties and weddings) are allowed on site; maximum attendees: 99 safety features at this property include a fire extinguisher and a deadbolt lock special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed 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

Reviews

Brad B.
Oct 3, 2025 12:49:37 AM
Review Score:   10
Summary: 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!
See All Reviews

FAQ's

Is this Historic District house pet-friendly for guests?

Yes, pets are allowed at this property. Check the guest reviews to learn what guests had to share.

Does the Historic District house have a swimming pool?

No, this Historic District house does not have a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in Historic District house?

Best-rates for the Historic District house starts from $1,271 per night with includes Security/Safety, Guest Services, Entertainment, Laundry, View, Ocean View, Sports/Activities, Bedding/Linens, Child Friendly, Pet Friendly, Hot Tub, Kitchen, Barbecue/Outdoor Cooking, TV, Balcony/Terrace, Wellness Facilities, Fireplace/Heating, Breakfast, Internet, Air Conditioner with all other facilities. matches every traveler with their perfect accommodation, whether you are traveling with a group, friends, family, or pets.

Is Historic District house a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this house Good or guests have recommended them suitable for families. As reported by the owner or manager, the house has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the Historic District house wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Historic District house has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the Historic District house?

Based on the information reported by the owner or manager, the Historic District house indicates 1 day stay policy at this house. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for Historic District house?

Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

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