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.

Enjoy cooking in this well-equipped kitchen with a stainless steel stove, double oven, and microwave.
Relax in a classic living room with a chandelier, armchairs, and a tufted sofa.
Stately brick building with a charming front porch and balcony, featuring evenly spaced windows and shutters.
Restful retreat with a large bed, tufted headboard, and comfortable seating area.
Enjoy meals in style with a beautifully set table for four, surrounded by a warm fireplace and elegant decor.

Reviews

9.4 out of 10
Exceptional

Entire home

6 bedrooms5 bathroomsSleeps 16

Popular amenities

  • Barbecue grill
  • Washer
  • Dryer
  • Kitchen
  • Pet friendly
  • Outdoor Space
The current price is ¥139,321
¥219,835 total
includes taxes & fees
Jul 21 - Jul 22

About this property

Entire place

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

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. CW fee applies!

Property manager

Sharon and Quinton Wilder

Languages

English

Add dates for prices

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
  • Ice maker
  • Kitchen island
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Stovetop
  • 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

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk
  • Desk chair

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • One pet total

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

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

Location highlights

  • In the city center
  • Near a health/beauty spa
  • Near a hospital
  • 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

Similar properties

Policies

Check-in

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

Check-out

Check-out before 12:00 PM

Special check-in instructions

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

Pets

Pets allowed
Service animals are welcome, and are exempt from fees
Welcoming dogs only
1 total pets
Note from host: Dogs not allowed in carpeted bedrooms

Children and extra beds

Children are welcome

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 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

About the neighborhood

Map
MD, Annapolis

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

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

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

How much does it cost to stay at NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.?

As of Jul 13, 2025, prices found for a 1-night stay for 2 adults at NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St. on Jul 21, 2025 start from ¥139,321, excluding taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

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.?

Check-out 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 vacation 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.

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

Reviews

9.4

Exceptional

Rating 10 - Excellent. 9 out of 11 reviews
Rating 8 - Good. 1 out of 11 reviews
Rating 6 - Okay. 0 out of 11 reviews
Rating 4 - Poor. 1 out of 11 reviews
Rating 2 - Terrible. 0 out of 11 reviews

9.2/10

Cleanliness

Reviews

10/10

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

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

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

10/10

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

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

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

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