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

9.4 (19 Reviews) |   Pet Friendly   6 Bedrooms  4 Bathrooms  16 Guests
Annapolis House | Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

6 Bedroom House in Annapolis

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!

Spacious historic home downtown Annapolis Main St Book for Commissioning Week! is located in Annapolis. Spacious historic home downtown Annapolis Main St Book for Commissioning Week! provides accommodation, featuring Bedding/Linens, Wellness Facilities, Fireplace/Heating, among other amenities. This House features Bedding/Linens, Wellness Facilities, Fireplace/Heating, to make your stay a comfortable one.

Spacious historic home downtown Annapolis Main St Book for Commissioning Week! has 6 Bedrooms , 4 Bathrooms, and max occupancy of 16 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the Annapolis has interesting places to visit. If you want to learn more about the House in Annapolis, such as places to visit and things to do nearby, you can check below to learn more.

Show more
OneKey Logos

This Property is OneKey Eligible

Earn OneKeyCash for every dollar spent on eligible vacation rentals, villas, cottages, cabins, and more when you book on Vrbo.

JOIN TODAY

Amenities

Air Conditioner
Pet Friendly
TV
View
Ocean View
Balcony/Terrace
Security/Safety
Sports/Activities
Bedding/Linens
Wellness Facilities
Fireplace/Heating
Guest Services
Entertainment
Breakfast
Barbecue/Outdoor Cooking
Child Friendly
Hot Tub
Internet
Kitchen
Laundry

Policies

Check-in
Check-in time starts at 4:00 pm minimum check-in age: 18
Check-out
Check-out before 11:30 am
Child Policy
Children are welcome.
Pet Policy
1 total pets note from host: dogs not allowed in carpeted bedrooms pets allowed service animals are welcome, and are exempt from fees welcoming dogs only

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 host has indicated there is a carbon monoxide detector on the property host has indicated there is a smoke detector on the property note from host: other fees may occur for commissioning week/events parties and events (including family gatherings, birthday parties and weddings) are allowed on site; maximum attendees: 99 safety features at this property include a fire extinguisher and a deadbolt lock special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed 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

Reviews

Joseph C.
Sep 1, 2025 12:30:44 AM
Review Score:   10
Summary: Great place, excellent location!
See All Reviews
Check House Availability
Nightly rates from:
USD US $1,298
You will be redirected to  
Hot Deal - It has been viewed 66 times today
Not the right fit? Check out our other properties in Annapolis
PERFECT LOCATION in the heart of history From US $447
         

10.0 (213 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Neptune By The Water From US $991
         

|
10.0 (6 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Vintage Charm: Annapolis Retreat From US $365
         

|
10.0 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • View
Pet-Friendly Beach Getaway, Relax by the Bay! From US $267
         

|
10.0 (4 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Rare find! Chic cottage, salt water heated pool May 15-Oct15. From US $871
         

Oasis by the Bay - Waterfront Heated Pool Hot Tub From US $955
         

|
10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Nautical Feel to This Beautiful Eastport Home From US $573
         

9.8 (57 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Chesapeake Bay single family home From US $597
         

9.6 (19 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Charming Annapolis WaterVIEW Home From US $562
         

9.8 (58 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
The Yellow Cottage on Harness Creek From US $307
         

10.0 (170 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV