Entire home

Grand, historic, fun, fabulous home - downtown Annapolis at Main St. & City Dock

Photo gallery for Grand, historic, fun, fabulous home - downtown Annapolis at Main St. & City Dock

Exterior
Breakfast meal
Room
Living area
Private kitchen

Reviews

10 out of 10
Exceptional
6 bedrooms4+ bathroomsSleeps 16353.0 sq m

Popular amenities

  • Barbecue grill
  • Washer
  • Dryer
  • Kitchen
  • Pet-friendly
  • Outdoor space

Explore the area

Map
Annapolis, MD
  • Annapolis City Dock
    ‪3 min walk‬
  • U.S. Naval Academy
    ‪9 min walk‬
  • Navy-Marine Corps Memorial Stadium
    ‪3 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

Grand, historic, fun, fabulous home - downtown Annapolis at Main St. & City Dock

The Oaks Inn is an exceptional home hjistoric nestled in the heart of Historic Downtown Annapolis that seamlessly combines timeless historic charm and original wood floors with luxury 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 in Annapolis boasts charm, ambiance, and serve as the perfect centerpiece for dining and entertaining. The back patio provides an enchanting oasis for relaxing fun.

The space
The Oaks in 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 sitting room which leads to the dining area and living room, thoughtfully designed to foster a harmonious flow between living spaces. The living room and dining room, boasting charm and ambiance, serves as the perfect centerpiece for dinner parties and for entertaining guests, friends and family. Ascending to the second 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 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
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Children

Children allowed: ages 0–17
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Events

Events allowed: family gatherings, birthday parties, weddings
Other fees may occur for commissioning week/events
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Pets

Pets allowed: dogs (limit 1 total)
Dogs not allowed in carpeted bedrooms
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Smoking

Smoking is not permitted
1. Put towels in laundry area 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 Commissioning Week.
1.Take trash to garbage can outside. 2. Turn off lights, fans, and thermostats. 3. Close windows and curtains upon check out.

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.
Map
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

  • 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 Annapolis' Original Steakhouse - ‬2 min walk
  • ‪Chick & Ruth's Delly - ‬4 min walk
  • ‪Mc Garvey's Saloon - ‬3 min walk

Frequently asked questions

Is Grand, historic, fun, fabulous home - downtown Annapolis at Main St. & City Dock pet-friendly?

Yes, this property allows dogs (limit 1 total).

What time is check-in at Grand, historic, fun, fabulous home - downtown Annapolis at Main St. & City Dock?

Check-in begins at 3:30 PM.

What time is check-out at Grand, historic, fun, fabulous home - downtown Annapolis at Main St. & City Dock?

Checkout is at 10:30 AM.

Where is Grand, historic, fun, fabulous home - downtown Annapolis at Main St. & City Dock located?

Located in Historic District, this holiday 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.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 7 out of 7 reviews
Rating 8 - Good. 0 out of 7 reviews
Rating 6 - Okay. 0 out of 7 reviews
Rating 4 - Poor. 0 out of 7 reviews
Rating 2 - Terrible. 0 out of 7 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Amy R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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!
Stayed 7 nights in Dec 2024

10/10 Excellent

Kristina M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful historic home

Perfect place location and size for my friends and family for our Naval Academy reunion. Thank you!!
Stayed 3 nights in Nov 2024

10/10 Excellent

Leighton S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Weekend stay in Annapolis

Very comfortable home with the proximity to downtown. Loved it!!
Stayed 3 nights in Apr 2024

10/10 Excellent

Ryan M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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.
Stayed 2 nights in Aug 2024

10/10 Excellent

Adria E.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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!
Stayed 4 nights in Oct 2024

10/10 Excellent

Andrew H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Stay All Around

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.
Stayed 2 nights in Aug 2024

10/10 Excellent

Elizabeth B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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!!
Stayed 2 nights in Dec 2024

About the host

Hosted by Sharon and Quinton Wilder

Host profile image

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.

Languages:

English