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

9.4 (17 Reviews) |   Pet Friendly   6 Bedrooms  4 Bathrooms  16 Guests  Stay&Play
Annapolis House | Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

6 Bedroom House in 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 Annapolis. Spacious historic home downtown Annapolis Main St Book for Commissioning Week! provides accommodation, featuring Barbecue/Outdoor Cooking, Child Friendly, Kitchen, among other amenities. This House features Barbecue/Outdoor Cooking, Child Friendly, Kitchen, 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 Annapolis has interesting places to visit. If you want to learn more about the House in Annapolis, such as places to visit and things to do nearby, you can check below to learn more.

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Unique 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
 
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Policies

Event Policy Events allowed: family gatherings, birthday parties, weddings;maximum event attendees: 99;other fees may occur for commissioning week/events
Check-in Check-in time starts at 4:00 pm minimum check-in age: 18
Check-out Check-out before 11:30 am
Child Policy Children are welcome.
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
Other Policy 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
 
Annapolis, 21401, USA

What Our Guests say 500 + Reviews

Jul 9, 2025 08:45:15 AM
Summary: 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.
Dawn Y. Dawn Y.
Jun 23, 2025 10:49:35 PM
Summary: 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
Meg H. Meg H.
Jun 23, 2025 12:01:55 AM
Summary: 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.
Todd C. Todd C.
Jun 3, 2025 12:14:03 AM
Summary: Our group had a great time! This house was super convenient location and easily walkable to Main Street. Thank you!
Kerry G. Kerry G.
Dec 29, 2024 12:18:32 AM
Summary: 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!
Amy R. Amy R.
Dec 16, 2024 03:04:27 AM
Summary: 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!!
Elizabeth B. Elizabeth B.
Nov 18, 2024 11:17:20 AM
Summary: Perfect place location and size for my friends and family for our Naval Academy reunion. Thank you!!
Kristina M. Kristina M.
Oct 15, 2024 06:50:59 PM
Summary: 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!
Adria E. Adria E.
Aug 28, 2024 12:22:39 AM
Summary: 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.
Andrew H. Andrew H.
Aug 19, 2024 06:06:04 AM
Summary: 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.
Ryan M. Ryan M.

FAQ's

Is this Annapolis 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 Annapolis house have a swimming pool?

No, this Annapolis 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 Annapolis house?

Best-rates for the Annapolis house starts from $1,156 per night with includes Security/Safety, Wellness Facilities, Guest Services, Internet, Air Conditioner, Pet Friendly, Balcony/Terrace, Entertainment, Hot Tub, Laundry, TV, View, Sports/Activities, Bedding/Linens, Fireplace/Heating, Barbecue/Outdoor Cooking, Child Friendly, Kitchen, Ocean View, Breakfast StayAndPlay offers fully equipped golf villas, golf hotels, golf resorts, luxury golf cabins, and exclusive golf retreats, making it easier than ever to find your perfect golf escape — ideal for families, peaceful getaways, or pet-friendly retreats with the whole crew.

Is Annapolis 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 Annapolis house wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Annapolis 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 Annapolis house?

Based on the information reported by the owner or manager, the Annapolis 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 Annapolis house?

Based on the information reported by the owner or manager, details for the cancellation policy for the Annapolis house are as follows: Cancellation policy 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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