Entire home

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

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your current months are February, 2025 and March, 2025.
February 2025
March 2025

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

Parking
Smart TV, books, stereo
6 bedrooms, desk, iron/ironing board, free WiFi
Exterior
Fridge, microwave, oven, stovetop

Reviews

10 out of 10
Exceptional

Entire home

6 bedrooms5 bathroomsSleeps 16353 sq m

Popular amenities

  • Barbecue grill
  • Washer
  • Pet-friendly
  • Outdoor space
  • Breakfast available
  • Air conditioning

Explore the area

Map
Annapolis, MD
  • Annapolis City Dock
    ‪3 min walk‬
  • Ego Alley
    ‪5 min walk‬
  • Maryland State House
    ‪6 min walk‬
  • Annapolis, MD (ANP-Lee)
    ‪20 min drive‬

Room options

Similar properties

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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.
During your stay at this vacation home, you're just a quick walk from U.S. Naval Academy. Enjoy features like breakfast (surcharge), concierge services, and an arcade/game room. The vacation home includes amenities such as free WiFi and a jetted tub.
  • Air-conditioned home with kitchen, washing machine, and 4.5 bathrooms
  • Free WiFi
  • Breakfast is offered for a fee
  • Services include a concierge
  • Steps from Maynard-Burgess House and Kunta Kinte Plaque & Alex Haley Memorial
This vacation home offers its guests barbecue grills, an arcade/game room, and a garden. This vacation home also features concierge services, a water dispenser, and local meal delivery service. The front desk is open around the clock.

Property manager

Sharon and Quinton Wilder

Languages

English

Property amenities

Beach

  • Beach sunloungers
  • Beach towels

Internet

  • Free WiFi

Kitchen

  • Fridge
  • Stovetop
  • Microwave
  • Oven
  • Dishwasher
  • Spices
  • Electric kettle
  • Kitchen island
  • Toaster

Dining

  • Breakfast available for a fee
  • Dining table

Bedrooms

  • 6 bedrooms
  • Bed sheets provided

Bathrooms

  • 4.5 bathrooms
  • Bath or shower
  • Jetted
  • Toilet paper
  • Towels provided
  • Shampoo
  • Hairdryer
  • Soap

Living spaces

  • Living room
  • Dining room

Entertainment

  • Smart TV with cable/satellite service
  • Games room
  • Games
  • Stereo
  • Books

Outdoor areas

  • Balcony
  • Barbecue
  • Garden
  • Outdoor furniture
  • Firepit

Laundry

  • Washing machine and dryer

Work spaces

  • Desk
  • Desk chair

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • 1 total pets
  • Welcoming dogs only

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Concierge services
  • Chef
  • Iron/ironing board
  • Local meal delivery service

Location highlights

  • In the city centre
  • Near a health or beauty spa
  • Near the bay

Things to do

  • Power boating nearby
  • Sailing nearby
  • Marina nearby
  • Theme parks nearby
  • Cycling nearby
  • Fishing nearby
  • Golf nearby
  • Kayaking nearby
  • Basketball nearby

Safety features

  • Carbon monoxide detector installed (host has indicated that there is a carbon monoxide detector on the property)
  • Smoke detector installed (host has indicated that there is a smoke detector on the property)
  • Fire extinguisher
  • Deadbolt lock

General

  • At least 10% of profits reinvested in community and sustainability
  • At least 80% of lighting from LEDs
  • Recycling
  • Energy-saving switches
  • Local artist showcase
  • Unit size: 3800 sq ft (353 sq m)

Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age: 18

Check-out

Check-out before 11:30 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

  • Pets are welcome
  • Only dogs are allowed
  • Maximum 1 pets
  • Service animals are exempt from fees
  • Note from host: Dogs not allowed in carpeted bedrooms

Children and extra beds

  • Children are welcome.

Important information

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
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 there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadbolt lock
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
You will receive an email from the host with check-in and check-out instructions. You will also receive an email from Vrbo with a link to a Vrbo account which will enable you to manage your booking.

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

Reviews

10

Exceptional

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

Reviews

10/10 Excellent

Amy R.

Liked: Cleanliness
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

Elizabeth B., Milwaukee

Liked: Cleanliness
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

10/10 Excellent

Kristina M.

Liked: Cleanliness
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

Adria E., Guilderland NY

Liked: Cleanliness
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
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

Ryan M.

Liked: Cleanliness
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

Leighton S.

Liked: Cleanliness
Weekend stay in Annapolis
Very comfortable home with the proximity to downtown. Loved it!!
Stayed 3 nights in Apr 2024