Historic Happy Home Steps from Main Street w Private Yard, Screened-In Porch & Parking

Photo gallery for Historic Happy Home Steps from Main Street w Private Yard, Screened-In Porch & Parking

A covered porch with wicker furniture, a wooden ceiling, and large windows.
A white door with the number 117, a wooden fence, a metal gate, and a wooden wall with a window and shutters.
A living room with a sofa, coffee table, and a TV. There is a ceiling fan, a painting, and a plant.
A spacious kitchen with a central island, built-in cabinets, and a brick accent wall.
A dining area with a wooden table, chairs, a hanging light fixture, and a blue wall.

Reviews

10 out of 10
Exceptional

Highlights

  • The great outdoors
    Guests love the outdoor space here.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Walk to Maryland State House

Popular amenities

  • Deck or patio
  • Barbecue
  • Free Wi-Fi
  • Air-conditioning
  • Kitchen
  • Refrigerator

Explore the area

View map
Annapolis, MD
  • Place, Maryland State House
    ‪5 min walk‬
  • Place, Annapolis City Dock
    ‪6 min walk‬
  • Place, U.S. Naval Academy
    ‪8 min walk‬
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪39 min drive‬

Rooms & beds

3 bedrooms (sleeps 8)

2nd Floor Full

1 Double Bed

2nd Floor King

1 King Bed

3rd Floor Suite

1 Queen Bed

Living Room

1 Queen Sofa Bed

2 bathrooms, 1 half bathroom

Main Floor Powder Room

Toilet

Second Floor Hall

Bathtub · Toilet · Shower only

Third Floor Queen

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Number of living rooms
Garden

Add dates for prices

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  • Washing machine
  • Dryer
  • Pet-friendly
10.0 out of 10, Exceptional, (4 reviews)
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About the area

Annapolis

Located in Annapolis, this holiday home is in the city centre. Annapolis Harbor and Ego Alley are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Jonas Green State Park and Sandy Point State Park. Looking to enjoy an event or a game while in town? See what's happening at Tose Family Tennis Center or Alumni Hall.
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Map
Annapolis, MD

What's nearby

  • Thurgood Marshall Memorial - 5 min walk - 0.4 km
  • Maryland State House - 5 min walk - 0.4 km
  • Annapolis City Dock - 6 min walk - 0.6 km
  • William Paca House - 8 min walk - 0.7 km
  • U.S. Naval Academy - 8 min walk - 0.7 km

Getting around

  • Odenton Station - 22 min drive
  • Fort Meade, MD (FME-Tipton) - 33 min drive

Restaurants

  • ‪The Choptank - ‬7 min walk
  • ‪Starbucks - ‬5 min walk
  • ‪The Red Bean - ‬5 min walk
  • ‪Iron Rooster - ‬6 min walk
  • ‪McGarvey's Saloon & Oyster Bar - ‬7 min walk

Frequently asked questions

Is Historic Happy Home Steps from Main Street w Private Yard, Screened-In Porch & Parking pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Historic Happy Home Steps from Main Street w Private Yard, Screened-In Porch & Parking?

As of 31 October 2026, prices found for a 1-night stay for 2 adults at Historic Happy Home Steps from Main Street w Private Yard, Screened-In Porch & Parking on 1 December 2026 start from NZ$2,560, 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.

How much is parking at Historic Happy Home Steps from Main Street w Private Yard, Screened-In Porch & Parking?

On-site parking is available at the property.

What time is check-in at Historic Happy Home Steps from Main Street w Private Yard, Screened-In Porch & Parking?

Check-in begins at 4:00 PM.

What time is check-out at Historic Happy Home Steps from Main Street w Private Yard, Screened-In Porch & Parking?

Checkout is at 11:00 AM.

Where is Historic Happy Home Steps from Main Street w Private Yard, Screened-In Porch & Parking located?

Located in Historic District, this holiday home is within a 10-minute walk of Maynard-Burgess House and Annapolis City Dock. Spa Creek and Maryland Federation of Art are also within 5 minutes.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 36 out of 38 reviews
Rating 8 - Good. 2 out of 38 reviews
Rating 6 - Okay. 0 out of 38 reviews
Rating 4 - Poor. 0 out of 38 reviews
Rating 2 - Terrible. 0 out of 38 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

9.8/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We loved our stay in Annapolis!
Stayed 2 nights in Jul 2026
Response from VrboOwner on 15 August 2026
Thanks, Brandi! Please come back and stay with us again!
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Nice. A bit dated in parts. Light switches were archane and strange
Stayed 6 nights in Oct 2026
Response from VrboOwner on 19 October 2026
Thanks, Glenn, for the feedback, which we have shared with the owner. Glad to hear it was great stay for you and we hope to have you back again soon.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location and lovely home.
Stayed 2 nights in Apr 2026
Response from VrboOwner on 1 May 2026
Thanks, Jill! Please come back and stay with us again. Sean, iTrip Annapolis
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful home. Would stay again in a minute.
Stayed 2 nights in Oct 2025
Response from VrboOwner on 21 October 2025
Thanks, Julie! We’re thrilled to hear that Happy Hours impressed you and that you would stay again in a minute. We hope to host you again next time you’re in town! Melissa~iTrip Annapolis
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This property’s location cannot be beaten. Easy walks to historic Annapolis and across the bridge to Eastport. The house is charming with a wonderful screened in porch and cute backyard. The house is very well appointed and had everything we needed. Communication with the host was perfect. I highly recommend this property.
Stayed 2 nights in Apr 2026
Response from VrboOwner on 13 April 2026
Thanks, Erin! We are so happy you enjoyed everything. We look forward to hosting you again next time you’re here. Sean, iTrip Annapolis
Verified review

10/10 Excellent

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

Great Annapolis Location

Great place and location.
Stayed 3 nights in Sep 2024
Response from VrboOwner on 17 September 2024
Hi Dana! Thank you for being a great guest & we welcome you back anytime! Thank you for sharing your positive feedback, we sincerely appreciate knowing you enjoyed your time in the home, Melissa~iTripAnnapolis
Verified review

10/10 Excellent

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

Great trip

Fantastic property and location
Stayed 4 nights in Oct 2024
Response from VrboOwner on 15 October 2024
Thank you for staying with us & for your positive feedback! We welcome you back anytime! Melissa~iTripAnnapolis
Verified review

10/10 Excellent

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

Great location!

Wonderful neighborhood & walkable to everything! Thank you for the great stay!
Stayed 3 nights in Jun 2023
Response from VrboOwner on 26 June 2023
Thank you Rick for the kind review of Happy Hours. We are happy to hear you enjoyed your stay. Please come back and stay with us again. Safe Travels! -Tiffany
Verified review

10/10 Excellent

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

Awesome stay!

Great place! Wonderful location. We loved the quaintness of the house, The screened in patio was amazing! Would love to stay there again while visiting our daughter at USNA!
Stayed 4 nights in Aug 2023
Response from VrboOwner on 27 August 2023
Thank you Lisa! We are so happy to hear you enjoyed Happy Hours. Please come back and stay with us again. Safe Travels! -Tiffany
Verified review

10/10 Excellent

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

Great location and cute property

The house was perfect for us and would be amazing in Spring or Summer with the back porch and yard. Very well laid out and convenient to everything in Annapolis.
Stayed 2 nights in Dec 2024
Response from VrboOwner on 14 January 2025
Hi Shannon! Thank you for being a great guest & we welcome you back anytime! Thank you for sharing your positive feedback, we sincerely appreciate knowing you enjoyed your time in the home, Melissa~iTripAnnapolis
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location
Great Location and house worked perfectly for 4 adults. Parking needs to be addressed with possibly a closer parking deck being an option.
Stayed 2 nights in Aug 2025
Verified review

10/10 Excellent

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

Charming house with great location

A perfect stay for our family within walking distance of all the shops and restaurants. We loved the TV room in the back of the house with plenty of couch seating for all. Great communication from the house management co. during our stay too.
Stayed 3 nights in Nov 2024
Response from VrboOwner on 3 December 2024
Thank you for staying with us, Colleen & for your positive feedback! We welcome you back anytime! Melissa~iTripAnnapolis
Verified review

10/10 Excellent

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

60th birthday celebration weekend

We had an amazing stay in this beautiful home in the heart of the city dock. It was easy access to everything and the host was easy to reach and helpful with changes to check in times. Will definitely consider staying here again.
Stayed 2 nights in Nov 2024
Response from VrboOwner on 14 November 2024
Hi Nancy! Thank you for being a great guest & we welcome you back anytime! Thank you for sharing your positive feedback, we sincerely appreciate knowing you enjoyed your time in the home, Melissa~iTripAnnapolis
Verified review

10/10 Excellent

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

Perfect Stay

From the moment we reserved this location to the time we checked out we could not be happier with the entire experience. I highly recommend this location and want to thank those involved for making this a five star experience.
Stayed 3 nights in Jun 2024
Response from VrboOwner on 6 July 2024
Thank you for staying with us Skyler & for your positive feedback! We welcome you back anytime! Melissa~iTripAnnapolis
Verified review

10/10 Excellent

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

Great house

The house had everything we needed and was in a great place.
Stayed 2 nights in Mar 2023
Response from VrboOwner on 18 April 2023
Thank you for the kind review of Happy Hours Gregory! We hope to have the opportunity to host you again. Safe Travels! -Tiffany
Verified review

10/10 Excellent

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

Had a great time!

We enjoyed the place very much! My son loved the backyard and toys and my 6 month old slept really well in the one of three bedrooms. Proximity to town was perfect as well for a family of four. Very happy with our stay and I'm sure we'll be back.
Stayed 2 nights in Sep 2023
Response from VrboOwner on 22 September 2023
Thank you Katherine! We are so happy to hear you enjoyed Happy Hours. We hope to have the opportunity to host you again. Safe Travels! -Tiffany
From a partner site

10/10 Excellent

Best Place to Stay in Annapolis!

Happy Hours is the perfect place to stay in Annapolis! The house is beautiful (especially loved relaxing on the back porch!) and the location is right downtown on a quiet street near the water. Everything was perfect, I lucked out in getting this place! Hope to return!
Response from VrboOwner on 24 October 2023
Thanks, Brian’. We hope to host you again. Sean
Verified review

10/10 Excellent

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

Location and comfort

Great location in historic Annapolis. It was raining for our stay so walk to parking felt more like 15 minutes but when the sun came out it was better. Great bed, bedding and towels! Lovely family room. Enjoyed our stay.
Stayed 2 nights in Mar 2023
Response from VrboOwner on 28 March 2023
Thank you for the kind review of Happy Hours Karry. We are happy to here you enjoyed your stay. We would love the opportunity to host you again. Safe Travels! -Tiffany
Verified review

10/10 Excellent

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

Historic and perfectly situated

Wonderful property situated right in the historic district of Annapolis. Walking distance to the waterfront and main Street shopping and restaurants. The rooms were very good size with plenty of updated amenities to make our stay comfortable and perfect. I wish the parking was a little closer but overall I couldn't have asked for a better stay in Annapolis.
Stayed 2 nights in Nov 2023
Response from VrboOwner on 21 November 2023
Thanks, Kelly. Yes, parking is tricky - there is a much closer garage, but it’s $22/day, as opposed to included with the further-away option. Anyway, so glad you had a 5-star experience despite that. Please come back and stay with us again! Sean
Verified review

10/10 Excellent

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

Wedding house rental

The location and size of the house couldn’t have been better for our family to rent for our son’s wedding. Lots of character, great porch, nice kitchen!!
Stayed 4 nights in Nov 2024
Response from VrboOwner on 3 December 2024
Hi Catherine! Thank you for allowing us to host your stay & we are thrilled to know you enjoyed your time in the home! We welcome you back anytime, Melissa~iTripAnnapolis
Verified review

10/10 Excellent

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

Cute, Historical and Convenient

Cute place on a quiet and convenient street. Wonderful stroll to breakfast places and shopping and waterfront. Very clean and great support and communication from the operating team. Glad we stayed.
Stayed 2 nights in Jun 2024
Response from VrboOwner on 21 June 2024
We love hearing how much you enjoyed your stay with us Kathy! Thank you for your positive feedback & we welcome you to come stay again!
Verified review

10/10 Excellent

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

Perfect for USNA Visit

We stayed here for Parents weekend at USNA. The location was ideal so close to everything. The screened in porch was great as well and different spaces for privacy for our plebe. Plenty of space for the family. 5 Stars for sure.
Stayed 4 nights in Aug 2024
Response from VrboOwner on 27 August 2024
Thank you for staying with us, William & for your positive feedback! We welcome you back anytime! Melissa~iTripAnnapolis
Verified review

10/10 Excellent

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

Fantastic location and house

I came in town from Charlotte, NC for best friends birthday. The house was excellent. Walking distance to everything. Experience from Initially booking to the end of our stay was tremendous
Stayed 2 nights in May 2024
Response from VrboOwner on 13 May 2024
Hi Donald! Thank you for allowing us to host your stay & for sharing your positive experience, we welcome you back anytime! Melissa~iTripAnnapolis
Verified review

10/10 Excellent

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

Fall Weekend USNA

Wonderful place in superb location. Walking distance to downtown and beautiful neighborhood waterfront park. House had lovely open floor plan with homey living room, screened in area and beautifully kept backyard- greet gathering spot.
Stayed 2 nights in Oct 2023
Response from VrboOwner on 30 October 2023
Thanks, Alicia! So glad you enjoyed everything. Please come back and stay with is again any time. Sean
Verified review

10/10 Excellent

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

Exactly what you are looking for

Close to downtown, clean and comfy. Thank you
Stayed 2 nights in May 2023
Response from VrboOwner on 22 May 2023
Thank you for the kind review Russell. We are happy to hear you enjoyed your stay. We hope to have the opportunity to host you again. Safe Travels! -Tiffany
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