Entire home
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
Photo gallery for NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.





Reviews
10 out of 10
Exceptional
6 bedrooms 4+ bathrooms Sleeps 16 353.0 sq m
Popular amenities
Explore the area

Annapolis, MD
- Annapolis City Dock3 min walk
- U.S. Naval Academy9 min walk
- Navy-Marine Corps Memorial Stadium3 min drive
- Annapolis, MD (ANP-Lee)20 min drive
Rooms & beds
6 bedrooms (sleeps 16)
Bedroom 1
1 King Bed
Bedroom 2
1 King Bed and 1 Queen Bed
Bedroom 3
1 Queen Bed
Bedroom 4
1 Queen Bed
Bedroom 5
1 Queen Bed
Bedroom 6
2 Double Beds
Office 1
3 Single Beds
4 bathrooms, 1 half bathroom
Bathroom 1
Soap · Towels provided · Bathtub or shower · Jetted bathtub · Shampoo · Hair dryer
Bathroom 2
Soap · Towels provided · Bathtub or shower · Toilet · Jetted bathtub · Shampoo · Hair dryer
Bathroom 3
Soap · Towels provided · Bathtub or shower · Toilet · Jetted bathtub · Shampoo · Hair dryer
Bathroom 4
Soap · Towels provided · Bathtub or shower · Jetted bathtub · Shampoo · Hair dryer
Bathroom 5
Toilet
Spaces
Deck or patio
Porch or lanai
Kitchen
Balcony
Separate dining area
Garden
Dining area
About this property
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.
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.
Property manager
Sharon and Quinton Wilder
Languages
English
Add dates for prices
Amenities
Kitchen
Washer
Dryer
Pet-friendly
Free WiFi
Air conditioning
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House Rules
Check in after 3:30 PM
Minimum age to rent: 18
Check out before 10:30 AM
Children
Children allowed: ages 0–17
Events
Events allowed: family gatherings, birthday parties, weddings
Other fees may occur for commissioning week/events
Pets
Pets allowed: dogs (limit 1 total)
Dogs not allowed in carpeted bedrooms
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 that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock
About the area
Annapolis
Located in Historic District, a neighbourhood in Annapolis, this holiday 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, power boating and sailing offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling nearby.

Annapolis, MD
What's nearby
- Annapolis City Dock - 3 min walk - 0.3 km
- Maryland State House - 6 min walk - 0.5 km
- William Paca House - 6 min walk - 0.6 km
- U.S. Naval Academy - 9 min walk - 0.8 km
- Navy-Marine Corps Memorial Stadium - 3 min drive - 2.3 km
Getting around
Restaurants
- The Choptank - 3 min walk
- Starbucks - 2 min walk
- O'Brien's Annapolis' Original Steakhouse - 2 min walk
- Chick & Ruth's Delly - 4 min walk
- Mc Garvey's Saloon - 3 min walk
Frequently asked questions
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window10/10
Cleanliness
10/10
Check-in
10/10
Communication
10/10
Location
10/10
Listing accuracy
Reviews
28 Dec 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 7 nights in Dec 2024
10/10 Excellent
Elizabeth B.
15 Dec 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Army-Navy Weekend
Elizabeth B.
Stayed 2 nights in Dec 2024
10/10 Excellent
Kristina M.
18 Nov 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful historic home
Kristina M.
Stayed 3 nights in Nov 2024
10/10 Excellent
Adria E.
15 Oct 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect location with a huge yard
Adria E.
Stayed 4 nights in Oct 2024
10/10 Excellent
Andrew H.
27 Aug 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect Stay All Around
Andrew H.
Stayed 2 nights in Aug 2024
10/10 Excellent
Ryan M.
18 Aug 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Annapolis home
Ryan M.
Stayed 2 nights in Aug 2024
10/10 Excellent
Leighton S.
21 Apr 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Weekend stay in Annapolis
Leighton S.
Stayed 3 nights in Apr 2024
About the host
Hosted by Sharon and Quinton Wilder

Why they chose this property
Fun town; great restaurants and nightlife; nearby sailing and boating.
What makes this property unique
This immaculate Inn presents an extraordinary opportunity to stay in a historic property that seamlessly combines timeless historic charm and original wood floors with modern luxury furnishings and bedding. Ideally situated just a short stroll away from renowned landmarks such as the Naval Academy and City Dock, as well as the bustling ambiance of Main Street, State Circle and Maryland Avenue, 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 game room which leads to a chef’s kitchen and back bar, thoughtfully designed to foster a harmonious flow between living spaces. The living room and dining room boasts charm and ambiance, and serve as the perfect centerpiece for entertaining guests, friends and family.
Step inside the charming portico into the game room which leads to a chef’s kitchen and back bar, thoughtfully designed to foster a harmonious flow between living spaces. The living room and dining room boasts charm and ambiance, and serve as the perfect centerpiece for entertaining guests, friends and family.
Languages:
English
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