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.

Exterior
Breakfast meal
Room
Living area
Private kitchen

Reviews

9.4 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

View map
Annapolis, MD
  • Annapolis City Dock
    ‪3 min walk‬
  • U.S. Naval Academy
    ‪3 min walk‬
  • Navy-Marine Corps Memorial Stadium
    ‪3 min drive‬
  • Washington, DC (DCA-Ronald Reagan Washington National)
    ‪51 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. Please note: summer A/C and CW fee applies!

Add dates for prices

Amenities

Kitchen
Washing machine
Dryer
Pet-friendly
Free WiFi
Air conditioning

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Similar properties

House Rules

Check in after 4:00 PM
Minimum age to rent: 18
Check out before 12:00 PM
default

Children

Children allowed: ages 0–17
default

Events

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

Pets

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

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 CW plus fee added
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
  • U.S. Naval Academy - 3 min walk - 0.3 km
  • Maryland State House - 5 min walk - 0.4 km
  • Annapolis Maritime Museum - 17 min walk - 1.5 km
  • Navy-Marine Corps Memorial Stadium - 3 min drive - 2.5 km

Getting around

  • Odenton Station - 22 min drive
  • Fort Meade, MD (FME-Tipton) - 31 min drive

Restaurants

  • ‪Starbucks - ‬2 min walk
  • ‪The Choptank - ‬3 min walk
  • ‪Chick & Ruth's Delly - ‬4 min walk
  • ‪Mc Garvey's Saloon - ‬3 min walk
  • ‪Federal House - ‬2 min walk

Frequently asked questions

Is NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St. pet-friendly?

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

What time is check-in at NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.?

Check-in begins at 4:00 PM.

What time is check-out at NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.?

Checkout is at 12:00 PM.

Where is NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St. 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.

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

Premier Host

They consistently provide great experiences for their guests