Entire home

Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

Holiday home with kitchen, a short walk to U.S. Naval Academy

Photo gallery for Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

Fridge, microwave, oven, stovetop
Exterior
6 bedrooms, desk, iron/ironing board, free WiFi
Smart TV, books, stereo
Dining
Nestled in Historic Downtown Annapolis, The Oaks Inn combines timeless charm with luxury furnishings and bedding. Ideally situated steps from City Dock, this property offers six bedrooms each with a King or Queen bed and one two-bedroom suite with King and Queen beds. Enjoy the vibrant energy of downtown while relishing comfort on the private balcony or rooftop deck.

Reviews

9.4 out of 10
Exceptional

Entire home

6 bedrooms5 bathroomsSleeps 16353 sq m

Popular amenities

  • Washer
  • Dryer
  • Kitchen
  • Barbecue grill
  • Outdoor space
  • Pet-friendly
The current price is NZ$2,021
includes taxes & fees
23 Oct - 24 Oct

Add dates for prices

About this property

Entire place

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

Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

The Oaks Inn is a well-kept home, built in 1930 with original hardwood floors. It is nestled in the heart of Historic Downtown Annapolis and seamlessly combines timeless historic charm and original architecture 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 spacious brick back patio provides an enchanting oasis for relaxing fun. And the lawn area is perfect for outdoor games. There is an outdoor grill, heat lamps and a firepit for your outside enjoyment.

The space
The Oaks Inn Annapolis is a beautiful 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 suite with two double beds and a furnished rooftop deck. 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 through the charming portico into back yard and side door that leads to the charming sitting room, dining area and living room to the right and game/tv room, kitchen and bar lounge area to the left. The home is 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!

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

  • Laundry facilities
  • 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 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 11:30 AM

Special check-in instructions

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

Rules

2 night min holidays 1. Put towels in laundry 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- take to curb if Sunday 2. Turn off lights, fans, and thermostats. 3. Close windows and curtains upon check out.

Pets

Pets are 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

Events

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

Smoking

Smoking is not permitted

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
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 area

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

  • ‪The Choptank - ‬3 min walk
  • ‪O'Brien's Oyster Bar & Seafood Tavern - ‬2 min walk
  • ‪Starbucks - ‬2 min walk
  • ‪Annapolis Market House - ‬3 min walk
  • ‪McGarvey's Saloon & Oyster Bar - ‬3 min walk

Frequently asked questions

Is Spacious historic home downtown Annapolis Main St. Book for Commissioning Week! pet-friendly?

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

How much does it cost to stay at Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!?

As of 22 Oct 2025, prices found for a 1-night stay for 2 adults at Spacious historic home downtown Annapolis Main St. Book for Commissioning Week! on 23 Oct 2025 start from NZ$2,021.35, including 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 Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!?

Check-in begins at 4:00 PM.

What time is check-out at Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!?

Checkout is at 11:30 AM.

Where is Spacious historic home downtown Annapolis Main St. Book for Commissioning Week! 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.

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