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

Top rated by guests
Exterior
Private kitchen
Outdoor dining
Outdoor dining
Lawn Wedding
review stars
9.2Outstanding
(24 Ratings)
"The owners were very good with pre and post-check in communications, and were on site to meet us and show us the property. It was an excellent stay with an excellent location. Kitchen was well stocked..."
Ward U.
Don't miss out! Price and availability may change
9.2 / 10
Outstanding(24 Ratings)

House in Spa Creek, MD

16 guests · 6 bedrooms · 4 baths

Reasons to book

Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
Top-tier experienceA high end property in this area

About this house rental

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!

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

Non-smoking
Pets allowed
Family friendly

Map of Spa Creek, MD


Ratings and reviews

9.2 / 10
Outstanding(24 Ratings)
10 / 10Outstanding·Dec 2025
The owners were very good with pre and post-check in communications, and were on site to meet us and show us the property. It was an excellent stay with an excellent location. Kitchen was well stocked and lots of room for everyone.
10 / 10Outstanding·Nov 2025
we had a wonderful time! House was beautiful, will definitely be back!
10 / 10Outstanding·Nov 2025
The host was very welcoming and helpful. The house was a perfect location and walk to everything! Many bedrooms, bathrooms, coffee makers, balconies, yard with many places to sit, and easy to find. Perfect for our girls weekend and we all had our own bedrooms
8 / 10Excellent·Oct 2025
Extremely spacious for my family located close to many Annapolis historic sites, restaurants and shopping. Close to the USNA what we needed. Lots of living and entertainment spaces. The yard is huge, great for gatherings.

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FAQs

Is parking included with this house?

Parking is not specified as an available amenity at Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.

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

Yes! This house is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.

What amenities are available at Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!?

We found 3 amenities for this rental. This includes non-smoking, pets allowed, and family friendly.