Spacious Historic Home Downtown Annapolis Main St. Book for Commissioning Week!
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Spacious Historic Home Downtown Annapolis Main St. Book for Commissioning Week!

Annapolis, Maryland 21401, United States
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Amenities
Golf Course
Basketball Court
Wi-Fi in Public Areas
Concierge Service
Kayaking
Sailing
Beach Towel
Game Room
All amenities
Property Description
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!About pets:Pets allowed: dogs (limit 1 total).Dogs not allowed in carpeted bedrooms.About checkOut:Check out before 11:30 AM.About children:Children allowed: ages 0-17.About customRules:2 night min holidays 1. 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..About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 18.About events:Events allowed: family gatherings, birthday parties, weddings.Maximum event attendees: 99,Other fees may occur for commissioning week/events.
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10.0/10
Outstanding
Cleanliness10.0
Amenities10.0
Location10.0
Service10.0
All 18 reviews
Surroundings
Airport: Baltimore/Washington International Airport
(41.6km)
Train: Odenton
(30.9km)
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Overview

Rooms

Guest Reviews

Services & Amenities

Policies

Host

15

6 Bedrooms Private Vacation Home

6 bedrooms: 4 queen beds 2 king beds and 2 double beds
Free Wi-Fi
Non-smoking
Air conditioning
Refrigerator
TV
Wi-Fi in room
Room Details
Check Availability

Guest Reviews

10.0/10
Outstanding
18 reviews
Verified Reviews
  • Cleanliness10.0
  • Amenities10.0
  • Location10.0
  • Service10.0
Average for similar properties in Annapolis
Most Mentioned
D‍a‍w‍n‍ ‍Y‍.
July 9, 2025
I-Day send off 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.
T‍o‍d‍d‍ ‍C‍.
June 23, 2025
Very disappointing stay 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.
M‍e‍g‍ ‍H‍.
June 23, 2025
Great girls trip getaway 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
K‍e‍r‍r‍y‍ ‍G‍.
June 3, 2025
Annapolis Girls Weekend! Our group had a great time! This house was super convenient location and easily walkable to Main Street. Thank you!
A‍m‍y‍ ‍R‍.
December 29, 2024
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!
E‍l‍i‍z‍a‍b‍e‍t‍h‍ ‍B‍.
December 16, 2024
Army-Navy Weekend 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!!
K‍r‍i‍s‍t‍i‍n‍a‍ ‍M‍.
November 18, 2024
Beautiful historic home Perfect place location and size for my friends and family for our Naval Academy reunion. Thank you!!
A‍d‍r‍i‍a‍ ‍E‍.
October 15, 2024
Perfect location with a huge yard 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!
R‍y‍a‍n‍ ‍M‍.
August 19, 2024
Annapolis home 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.

Services & Amenities

More Amenities
Internet
Front desk services
Health & wellness
Activities
Public areas

Property Policies

Check-in and Check-out Times
Check-in: after 16:00
Check-out: Before 11:30
Child policies
Children of all ages are welcome at this property.
Additional fees may be charged for children using existing beds. Add the number of children to get a more accurate price.

Cots and Extra Beds
Please contact the hotel for details about cot and extra bed policies.

Age Requirements
The main guest checking in must be at least 18 years old

Property host

Sharon and Quinton Wilder
Speaks English

About this property

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!About pets:Pets allowed: dogs (limit 1 total).Dogs not allowed in carpeted bedrooms.About checkOut:Check out before 11:30 AM.About children:Children allowed: ages 0-17.About customRules:2 night min holidays 1. 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..About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 18.About events:Events allowed: family gatherings, birthday parties, weddings.Maximum event attendees: 99,Other fees may occur for commissioning week/events.
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Frequently Asked Questions

What is the cancellation policy for Spacious Historic Home Downtown Annapolis Main St. Book for Commissioning Week!?

The cancellation policy for Spacious Historic Home Downtown Annapolis Main St. Book for Commissioning Week! varies depending on the type of room and booking conditions.

How much does it cost at Spacious Historic Home Downtown Annapolis Main St. Book for Commissioning Week!?

Prices at Spacious Historic Home Downtown Annapolis Main St. Book for Commissioning Week! change according to dates, hotel policy, and other factors. Please search for the dates you wish to stay to view prices.

What are Spacious Historic Home Downtown Annapolis Main St. Book for Commissioning Week! nearby landmarks?

Nearby attractions to Spacious Historic Home Downtown Annapolis Main St. Book for Commissioning Week! include Museum of Historic Annapolis, only 100m from your search (straight-line distance) away.

What are check-in & check-out time at Spacious Historic Home Downtown Annapolis Main St. Book for Commissioning Week!?

Check-in at Spacious Historic Home Downtown Annapolis Main St. Book for Commissioning Week! starts from 16:00, and the standard check-out time is by 11:30.

About This Property

Nearest AirportBaltimore/Washington International Airport
Distance to Airport41.59KM
Nearest Train StationOdenton
Distance to Train Station30.9KM
Hotel Star Rating4