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Entire home

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

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

Photo gallery for NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.

Fridge, microwave, oven, stovetop
Dining
Smart TV, books, stereo
6 bedrooms, desk, iron/ironing board, free WiFi
Exterior
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 AU$1,917
includes taxes & fees
13 Oct - 14 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.

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!

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

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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

Rules

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.

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
  • ‪Starbucks - ‬2 min walk
  • ‪O'Brien's Oyster Bar & Seafood Tavern - ‬2 min walk
  • ‪McGarvey's Saloon & Oyster Bar - ‬3 min walk
  • ‪Annapolis Market House - ‬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 28 Sept 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 13 Oct 2025 start from AU$1,916.74, 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 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.

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Reviews

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

9.4

Exceptional

9.4

Cleanliness

10

Location
Rating 10 - Excellent. 11 out of 14 reviews
Rating 8 - Good. 2 out of 14 reviews
Rating 6 - Okay. 0 out of 14 reviews
Rating 4 - Poor. 1 out of 14 reviews
Rating 2 - Terrible. 0 out of 14 reviews

Reviews

8/10 Good

Kerry G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Annapolis Girls Weekend!

Our group had a great time! This house was super convenient location and easily walkable to Main Street. Thank you!
Stayed 2 nights in May 2025

10/10 Excellent

Meg H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great girls trip getaway

The house was perfect for our needs. There were lots of bedrooms and communal spaces. The kitchen is fully stocked which was a bonus. You couldn’t ask for a better location, everything is within walking distance. There is even a short cut from the parking garage to the house. Highly recommend this listing
Stayed 1 night in Jun 2025

10/10 Excellent

Amy R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

Ryan M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

Kristina M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

Elizabeth B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

Adria E.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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, check-in, communication, location, listing accuracy

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

Leighton S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Weekend stay in Annapolis

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

4/10 Poor

Todd C.

Liked: Location
Disliked: Cleanliness, check-in, communication, listing accuracy

Very disappointing stay

Extremely disappointed. Began with wrong information about check in time. Followed by one bedroom not having a working air conditioner in 90 degree weather. Another bedroom air conditioner has hose on the ground, my husband went to get duct tape to repair. Repair man did show up to get bedroom working. Food left in refrigerator that was ours to use. Viking oven had a large oven that would not heat up , yet the two smaller oven did heat up. One bedroom had a fly problem. Bought spray, taped around the air conditioner, and the flies were back. Disgusting. Couldn’t use that bedroom for the last night. Let property manger know through text, no response. Every small area rug was filthy, shower curtains need liner replacement. We made the best of it. We loved Annapolis but we would never rent this home again. Also, large yard was spacious but unkept.
Stayed 3 nights in Jun 2025