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

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Step into this charming 1879 Annapolis home, blending historic cedar shake charm with modern comforts. Unwind on the spacious screened porch overlooking the private backyard or in the bright living room. The renovated kitchen, dining room seating 8 and powder room are perfect for entertaining.

Reviews

10 out of 10
Exceptional

Entire home

4 bedrooms3 bathroomsSleeps 82550 sq ft

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning
  • Outdoor space

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.

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

Laundry facilities, a garden and barbecues are available at this smoke-free holiday home. The holiday home has 3 bedrooms and offers free WiFi and a sofa bed. Guests will find a kitchen with a fridge, an oven, a stovetop and a microwave.
Air-conditioned accommodation at this holiday home offers coffee/tea makers and a hairdryer. Rooms open to patios. This accommodation is furnished with sofa beds and dining tables. Kitchens offer fridges, stovetops, microwaves and kitchenware and utensils. Bathrooms include a shower.

Guests can surf the web using complimentary wireless Internet access. Smart televisions are featured in guestrooms.

The recreational activities listed below are available either on-site or nearby; fees may apply.

Property amenities

Internet

  • Available in the house: Free WiFi

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Ice maker
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Toaster

Dining

  • Dining table

Bedrooms

  • 4 bedrooms
  • Bedsheets provided
  • Sofa bed

Bathroom

  • 2.5 bathrooms
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

  • Smart TV with cable/satellite channels

Outdoor areas

  • Barbecue grill
  • Garden
  • Outdoor furniture
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Printer

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the city centre

Things to do

  • Bicycles

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)

General

  • Bicycles
  • Garden
  • Unit size: 2,550 square feet

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Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in and check-out are available
Minimum check-in age - 25

Check-out

Check-out before 11:00 AM
Contactless check-out

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

Pets not allowed

Children and extra beds

Children are welcome

Events

No events allowed

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
On-site parties or group events are strictly prohibited
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
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
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

Property is also known as

11221

About the area

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. Take the opportunity to explore the area for outdoor excitement like hiking/biking trails. Visit our Annapolis travel guide
View more Holiday homes in Annapolis
Map
Annapolis, MD

What's nearby

  • Maryland State House
    Maryland State House
    5 min walk - 0.4 km
  • William Paca House
    William Paca House
    8 min walk - 0.7 km
  • U.S. Naval Academy featuring military items, heritage architecture and interior views
    U.S. Naval Academy
    8 min walk - 0.7 km
  • Hammond-Harwood House
    Hammond-Harwood House
    9 min walk - 0.8 km
  • Annapolis City Dock
    6 min walk - 0.6 km

Getting around

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

Restaurants

  • Starbucks
    5 min walk
  • Rams Head Tavern
    7 min walk
  • O'Brien's Oyster Bar & Seafood Tavern
    5 min walk
  • Buddy's Crabs & Ribs
    5 min walk
  • Chick & Ruth's Delly
    3 min walk

Frequently asked questions

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

No, pets are not allowed at this property.

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

Checkout is at 11:00 AM.

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

Located in Historic District, this holiday home is within a 15-minute walk of Maynard-Burgess House and U.S. Naval Academy. Spa Creek and Maryland Federation of Art are also within 5 minutes.

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

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
Rating 10 - Excellent. 29 out of 30 reviews
Rating 8 - Good. 1 out of 30 reviews
Rating 6 - Okay. 0 out of 30 reviews
Rating 4 - Poor. 0 out of 30 reviews
Rating 2 - Terrible. 0 out of 30 reviews

10

Cleanliness

10

Location

Reviews

10/10 Excellent

Dana D.

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

Great Annapolis Location

Great place and location.
Stayed 3 nights in Sep 2024

10/10 Excellent

Elizabeth M.

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

Great trip

Fantastic property and location
Stayed 4 nights in Oct 2024

10/10 Excellent

shannon r.

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

10/10 Excellent

Lisa R.

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

10/10 Excellent

Colleen M.

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

10/10 Excellent

Nancy W.

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

10/10 Excellent

Skyler G.

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

10/10 Excellent

katherine w.

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

10/10 Excellent

Catherine W.

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

10/10 Excellent

Kathy C.

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

10/10 Excellent

William E.

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

10/10 Excellent

Kelly J.

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

10/10 Excellent

Alicia H.

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

10/10 Excellent

Jeff & Heather W., Mount Pleasant, SC

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

Will be back!!!

We’ve rented numerous houses in Annapolis over the years, and this one just moved into one of the top spots! Very spacious, very clean, great location, etc.
Stayed 3 nights in Sep 2023

10/10 Excellent

Dean B.

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

Great property in Annapolis

We stayed here for our wedding weekend in town. We are very familiar with Annapolis and picked this house because the location is perfect and walkable to everything. The house itself was larger than expected with a great yard and porch. They even included special extras in the house when we arrived which was greatly appreciated. Everything was very smooth and professional. Would stay there again.
Stayed 3 nights in May 2024
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Phaedra L.

Great reunion weekend

We stayed at Happy Hours with 2 other couples for my husband’s 30th USNA reunion and the accommodations were perfect. We enjoyed the easy walk to downtown and the USNA Yard. Having a dedicated place to park in the parking garage during the boat show weekend was a nice benefit and was only a 10 minute walk from the house. Every part of the house was so comfortable to sit and visit and relax between reunion events. We would definitely recommend the house and will remember it in the future.

10/10 Excellent

Denise M.

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

Conduit Street- Great location!

We loved our stay in Conduit Street. The house was charming with all the features of a home built in the 1800’s . The screened in porch and beautiful back yard added to the ambience. It was very hot during our stay making it a little hard to walk around town for extended periods. The location of the property made it easy to take a brake and relax. We will be back.
Stayed 3 nights in Jun 2024

10/10 Excellent

Barbara V.

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

A quick trip

We loved this house! The house was ready for us and Cathy always respond to any question I had quickly. The location of the house was perfect. We walked around town daily . It is a quick walk to the center of town. the neighborhood was quiet. The best part of the house was the screened in porch. We sat out there every morning and evening. We had a great time with close friends. The house is spacious. We are looking forward to booking again.
Stayed 2 nights in Aug 2023

10/10 Excellent

Verified traveller

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

117 Conduit

This location was very welcoming, with fresh flowers and wine, nice touch. We had seven adults and there was plenty of room for all. The three bedrooms are spacious and well appointed. The common area was also spacious with a very nice screened deck and back yard. We used the kitchen facilities, all in good order and convenient. Very close to everything. Parking is tough, public street parking is by permit or paid with a two hour maximum, but ride share services are readily available.
Stayed 3 nights in Oct 2023
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Susan H.

Location-location-location!

The Happy Hours House at 117 Conduit was the perfect home for our group. With three couples, the accommodations were ideal with plenty of room for the time we spent at the home. The location could not have been more ideal as it is nestled on a quiet street just two blocks from Main Street and the path to anything you would want to do in Annapolis. Provided for us were all of the amenities that one would need such as dishwasher pods, two types of coffee, pots, and a tea kettle. The sheets and towels were up the highest quality and the staff from ITrip Responded over the weekend to questions we had. (Thank you Melissa). The description of the home is accurate so do keep in mind this home is a historic district so embrace the charm of the age of the home, but enjoy the updates to make your stay a pleasant one.

10/10 Excellent

Julie M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful home. Would stay again in a minute.
Stayed 2 nights in Oct 2025

8/10 Good

James M.

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

10/10 Excellent

Verified traveller

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

10/10 Excellent

Gregory K.

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
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Kelly S.

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!