Entire home

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

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

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

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

Reviews

10 out of 10

Exceptional

Entire home

6 bedrooms5 bathroomsSleeps 16353.0 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
  • Spa Creek
    4 min walk
  • Ellen O. Moyer Nature Park at Back Creek
    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 holiday home, you're just a quick walk from U.S. Naval Academy. Enjoy features like breakfast (surcharge), concierge services and an arcade/games room. The holiday home includes amenities such as free WiFi and in-room jetted baths.
  • 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
Grand, historic, fun, fabulous home - downtown Annapolis at Main St. & City Dock offers its guests barbecue grills, an arcade/games room, and a garden. Grand, historic, fun, fabulous home - downtown Annapolis at Main St. & City Dock 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 loungers
  • Beach towels

Internet

  • Available in the house: Free WiFi

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Hob
  • Ice maker
  • Kitchen island
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Toaster
  • Water dispenser

Dining

  • Breakfast available for a fee
  • Chef service
  • Dining table

Bedrooms

  • 6 bedrooms
  • Bedsheets provided

Bathroom

  • 4.5 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Jetted bathtub
  • Shampoo
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Living room
  • Separate dining area

Entertainment

  • Books
  • Games
  • Smart TV with cable/satellite channels
  • Stereo

Outdoor areas

  • Balcony
  • Barbecue grill
  • Firepit
  • Garden
  • Outdoor furniture

Laundry

  • Washing machine

Work spaces

  • Desk
  • Desk chair

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • One pet total

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Concierge services
  • Iron/ironing board
  • Meal delivery service

Location highlights

  • In the city centre
  • Near a health/beauty spa
  • Near the bay
  • Near the marina

Things to do

  • Arcade/game room
  • Basketball nearby
  • Cycling nearby
  • Fishing nearby
  • Golfing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Sailing nearby
  • Theme park nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated 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% lighting from LEDs
  • Energy-saving switches in guestrooms
  • Garden
  • Local artist showcase
  • Recycling
  • Unit size: 3,800 square feet
  • Water dispenser

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 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
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. 6 out of 6 reviews" "
Rating 8 - Good. 0 out of 6 reviews" "
Rating 6 - Okay. 0 out of 6 reviews" "
Rating 4 - Poor. 0 out of 6 reviews" "
Rating 2 - Terrible. 0 out of 6 reviews" "

10/10

Cleanliness

Reviews

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