Happy Hours

3 BR
2.5 Baths
Sleeps 8


Enjoy a piece of Annapolis history! Nestled at the end of a row, this circa 1879 home has the perfect blend of historic cedar shake charm on the outside combined with a surprisingly modern interior. The renovated kitchen with its exposed brick chimney, beautiful cabinets, granite countertops and breakfast bar overlooks the sunken great room with walls of windows and cathedral ceilings. Celebrate your Happy Hours on the spacious screened porch overlooking the private backyard. Back inside is a dining room with seating for 8 and bright living room in the front of the home with a new Queen sleeper sofa. There is also a powder room and full laundry room located on the main floor.

Head upstairs to the 3 oversized bedrooms and 2 bathrooms. The 2 guest bedrooms on the 2nd floor share the unique full bath in the hall, with separate shower/bath and double vanity/toilet rooms. The third-floor suite has a Queen bed, its own private full bath and even a delightful peek-a-boo view of the Maryland State House. Located one block to the quiet waters of Spa Creek and 2 blocks to Main Street, this home is just steps away from downtown shopping, restaurants, parks and historical sites, the Naval Academy and the Maryland State House.

***Parking is not on premises!! A dedicated parking spot at NEARBY GARAGE (10 minute walk) is provided. Please contact us for details.


3rd Floor Suite:

- Queen Bed

- Full ensuite bath with stand-up shower

King Bedroom:

- 2nd Floor

- King Bed

- Full bath in the hall with standup shower and soaking tub, double vanity

Full Bedroom:

- 2nd Floor

- Full Bed

- Full bath in the hall with standup shower and soaking tub, double vanity

Living Room

- Main Floor

- Queen sleeper sofa

- Half bath on the main floor; shared full bath in the hall on the 2nd floor


- Large Kitchen overlooking the sunny sunken den

- Breakfast bar in kitchen seats 2

- Dining room table seats 8

- Large screened-in porch

- Private backyard

- WiFi

- Big Screen Smart TV's

- 2 bicycles for guest use

- Luxury linens, complimentary toiletries Starter Kit, and boutique-level service

- Keurig and coffee pot with starter coffee and creamers

- Washer & dryer located inside the home

- Elderly and guests with mobility issues may want to inquire about the steep staircase and/or may want to consider other accommodations.

- Keyless entry. Drive straight to your rental home and enter the code for the electronic lock on the front door.

Property Distance to:

- U.S. Naval Academy – 5 blocks

- Washington, DC – 30 miles

- Baltimore - 25 miles

* Amenity & Supplies starter pack, coffee and sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid to get you going.

* All beds are ready made for you with freshly laundered sheets & towels.

House Rules

Reservations made for teenagers or young single groups will not be honored without any accompanying adult staying in the unit at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No smoking/no pets. Please respect the neighbors and neighborhood. No parties, events or smoking of any kind.

Check-in time: 4:00 pm

Check-out time: 11:00 am

117 Conduit St Annapolis, MD 21401
Registration Number: STR22-145159

Sleeping Arrangements

2nd Floor King King
2nd Floor Full Full
3rd Floor Suite Queen
Living Room Sofa Queen

Bathroom Configuration

Third Floor Queen: Shower, Toilet
Second Floor Hall: Shower, Toilet, Tub
Main Floor Powder Room: Toilet

Property Rules

Check In: After 4pm
Check Out: Before 11am
Smoking: Not Allowed


Air Conditioning
BBQ Grill
Bath Towels
Bed Linens
Big Screen TV
Carbon Monoxide Detector
Clothes Dryer
Coffee Maker
Cooking basics
Covered Patio
Dining room
Enhanced Cleaning
Full Kitchen
Hair Dryer
Historic Downtown
Ice Maker
Internet Access
Iron and Board
Living room
Open Patio
Parking Voucher for garage
Private Backyard
Private entrance
Screened Patio
Self Check-In
Smoke Detector
Smoke alarms
Travel crib
Washing Machine
body wash
hot water
portable crib



Frequently Asked Questions


Tenant is at least 25 years old (an "adult") and will be an occupant of the unit Happy Hours. Should any unauthorized persons occupy or use the Premises, Tenant shall vacate the premises immediately without any refund.


Balance is due 30 days prior to arrival date and includes a refundable damage deposit. The balance is due on _BalanceDueDate_. Payment may be made by major credit card. Damage deposit will be refunded within 7 -10 days of checkout pending inspection by cleaning firm.


Cancellations must occur at least 45 days prior to arrival date. If cancellation occurs 45 days or more prior to arrival date all monies will be refunded with the exception of a $100.00 administrative fee. GUESTS THAT DO NOT CANCEL WITHIN THE 45-DAY TIME FRAME WILL BE CHARGED THE FULL AMOUNT.


No BBQ grills of any kind are permitted in the unit. No open flames permitted in the unit.


Unless Pet Deposit Paid before Checkin.  If evidence of a pet(s) is found in the unit or on the premises you will be asked to vacate immediately with no refund of rent or damage deposit.


Any reservation obtained under false pretense will be subject to forfeiture of reservation deposit, damage deposit, and/or balance of rental payment.


There is no daily maid service. Linens and towels are included and not to be taken from the unit. There is a $_CleaningFee_ one time cleaning fee.


No compensation will be given for temporary outage of electricity, gas, water or cable. 


Your damage deposit will be forfeited and you will incur an additional charge for cleaning and deodorizing if any evidence of smoking is found.


Owner or owner's agents may enter the premises: in case of an emergency; to make any necessary or agreed upon repairs, alterations, or improvements; supply necessary or agreed upon services or show the premises to prospective purchasers, renters or contractors.  24 hours notice of Owners intent to enter will be given (except in the case of an emergency).


  1. Tenant agrees to leave the premises and its contents in the same condition, neat and tidy, as Tenant found the premises to be upon move-in, normal wear and tear expected. Beds should be stripped of linens and placed in a pile in each bedroom for housekeeping.
  2. All dishes are to be washed and all garbage removed from the premises and placed in outside receptacles. If these items are not completed, the guest will be charged an additional cleaning fee. 
  3. The maximum number of occupants shall not exceed 8 people, not including a child in a crib.
  4. Furnishings are not to be removed from the premises for use outside or in other properties.
  5. No pets allowed on premises - unless Pet Deposit paid for prior to check-in.
  6. No Smoking.
  7. Reservations are not made by or for a minor, defined as any person under the age of 25.
  8. Tenant and any guest of Tenant shall obey all laws of the state of Maryland, as well as local laws, at all times while they are on the premises. Failure to abide by the laws of Maryland or the above rules may cause tenant to be asked to vacate the premises and forfeit all rents and security/damage deposits.


Tenant and all other occupants will be required to vacate the premises and forfeit the rental fee and security deposit for: Occupancy exceeding the sleeping capacity of 8 people, using the premises for illegal activity, causing damage to the premises rented or to any of the neighboring properties and any other acts which interferes with neighbors' right to quiet enjoyment of their premises.


iTrip or the Owner, does not assume any liability for loss, damage or injury to persons or their personal property. Neither does owner accept any liability for any inconveniences, damage, loss or injury arising from any temporary defects or stoppage in supply of water, gas, cable service, electricity or plumbing, as well as due to weather conditions, natural disasters, acts of God, or other reasons beyond its control.


Please report any maintenance needs for the premises to the us and we will respond as quickly as possible. Refunds will not be made for maintenance issues including, but not limited to heating and air conditioning, appliances, televisions, and stereos.


Perfect location, perfect home
5/5 stars
We stayed here with our 2 children and significant others, 6 adults total. Great home with lots of seating areas, full kitchen, 2.5 bathrooms so no waiting! The outside porch is a real gem. You will be more than pleased if you decide to stay here. We loved it.
- Debbie

Thank you for staying with us Debbie & for your positive feedback! We welcome you back anytime! Melissa~iTripAnnapolis

- Manager Response
Great reunion weekend
5/5 stars
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.
- Phaedra
Great stay downtown Annapolis!
5/5 stars
We’ve rented many times in Annapolis & this place immediately became one of our favorites. Very spacious, well appointed & nice amenities. We will definitely book here again!
- Jeff
Awesome stay
5/5 stars
Stay was wonderful. House is perfect! Great location to be able to walk to town and to USNA. Loved the screened in porch!! Would love to come back and use this as our go to place!
- Lisa
5/5 stars
We truly enjoyed our stay at Happy Hours. The location couldn't be more convenient. The kitchen was stocked with everything we needed. There were 5 of us and plenty of room to roam. We mainly used the kitchen, TV room and we loved the back screened-in porch. The towels were wonderfully plush...no skimping there. Almost most importantly, we did not think Sears catalogue when needing the toilet paper. The claw footed tub was superb. The charms of this old historic home over-road the fact that the house has settled and the flooring slants to one side. Happy Hours is centrally located, in a very quiet residential area, within walking distance to everything we had in mind to accomplish. This was a huge plus since our car was parked .5 mile away in a parking garage. Another plus was the app which was very well organized with all the information we needed for the home and surrounding area. THANK YOU ITRIP!! We would definitely consider this property and your management company in the future. Thank you especially to Cathy Hochman for all your help!
- Toni
Best Place to Stay in Annapolis!
5/5 stars
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!
- Marie
Fantastic DTA Rental
5/5 stars
We recently rented the "Happy Hours" house during commissioning week for our daughter's graduation from the Naval Academy. It was, without a doubt, the best property we have ever rented in Annapolis, or anywhere else. The home itself is lovely and is a combination of modern amenities mixed with historical charm. It is very well furnished, the beds are comfortable, and it is stocked with more dishes, utensils, pots & pans, etc. than any place we have ever stayed. The inhouse washer and dryer was extremely convenient. Separate air conditioning zones allowed for individualized comfort in each of the 3 bedrooms. The screened in back porch was a lovely place to relax after a long day on the Yard and the backyard is beautiful. The location is perfect. Only 2 blocks from Main Street and all of its dining options, the docks, and shopping. We were able to walk to and from the Academy multiple times a day. It is close enough to be extremely convenient, but far enough away to be quiet and restful in the evenings. Parking is a bit of a challenge, since there is no onsite availability, but we were given a street parking pass that worked quite well and there is also a pass for a local parking garage that is only a 10 minute walk. We only had to use the parking garage 3 times during our 10 day stay. Communication with the landlord was effective but not intrusive. Our only regret is that we didn't discover this property 4 years ago. If you are looking for a wonderfully appointed house in downtown Annapolis to rent for up to 6 people, this is an ideal choice.
- Gordon

Book Your Stay

Select your trip dates.
Contact Manager

Phone (410) 571-4076