Deep in the Heart of Crabtown

3 BR
3.5 Baths
Sleeps 6


Welcome to this gorgeous Texas-themed downtown Annapolis home. Every inch of this home has custom finishes and has been painstakingly renovated by the gracious homeowner who recently opened his home to guests. And if the interior of the home isn't enough, the outdoors are a rare gem in the city: a yard, an oversized back deck, front porch and parking for 4 cars in the driveway.

Located just around the corner from the Waterfront, you can see the harbor boats and all the way to the Bay Bridge from the top floor Suite. There are 2 bedrooms and 2 full baths on the 2nd floor and a third floor suite with a Queen bedroom, full bath and living room. The home's large kitchen, breakfast bar and eat-in kitchen overlook the sunny back patio. There is a large family room and dining room with seating for ten. There is also a large entry foyer and lounge with custom artwork throughout.

This is the perfect spot for those coming in for that special Naval Academy or boat show event, or wanting to take in the sights and sounds of Greater Annapolis. Enjoy the many restaurants, historical attractions, and shops right around the corner!

SLEEPING ARRANGEMENTS 3 BR / 3.5 BA / Sleeps 6 adults (2 additional children):

2nd Floor Suite:

- Second Floor

- Queen Size Bed

- En Suite Bath with dual vanities and custom stand-up shower

Guestroom on the 2nd Floor:

- Second Floor

- Full-Size Bed

- Full Bath in the Hall

3rd Floor Bedroom Suite:

- Third Floor

- Queen Bed

- Full Bath

- Living Room with views of the Annapolis Harbor


- Oversized Back Patio with sitting area, brand new furniture and gas grill

- Spacious gourmet kitchen

- Eat-in kitchen counter seats 2

- Dining room table seats 8-10

- WiFi

- Big Screen TVs

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

- Parking for 4 cars

- 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.

- Touchless entry. Drive straight to your rental home, park in the driveway and enter the back door with the code we provide one week before checkin.

Property Distance to:

- U.S. Naval Academy – 3 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 already made for you with freshly -laundered luxury 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

90 Duke of Gloucester St Annapolis, MD 21401

Sleeping Arrangements

2nd floor Suite Queen
2nd floor Guestroom Full
3rd Floor Suite Queen

Bathroom Configuration

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

Property Rules

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


Air Conditioning
BBQ Grill
Bath Towels
Bay View
Bed Linens
Big Screen TV
Carbon Monoxide Detector
Clothes Dryer
Coffee Maker
Covered Patio
Enhanced Cleaning
Full Kitchen
Hair Dryer
Historic Downtown
Ice Maker
Internet Access
Iron and Board
Open Patio
Parking Available
Private entrance
Self Check-In
Smoke Detector
Smoke alarms
Washing Machine
Water View
body wash
hot water



Frequently Asked Questions


Tenant is at least 25 years old (an "adult") and will be an occupant of the unit Deep in the Heart of Crabtown. 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.


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


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. Please leave all used towels on the floors of the bathrooms and beds linens should all be left on each bed 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 6 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.
  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 6 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- Great home!
5/5 stars
This home was lovely! The kitchen area was large and inviting. The beds were incredibly comfy and the deck was the best to hang out on. The location was PERFECT and the extra parking was handy. Walking everywhere was possible and the ITrip company was immediately responsive whenever needed. Owners were easy to work with. I recommend this location!
- Beth

Hi Beth- Thank you for your positive feedback & for letting us know you enjoyed your stay! We welcome you back to stay again, anytime! Melissa~iTripAnnapolis

- Manager Response
Great house and location
5/5 stars
This is the best house wehave ever stayed at in our many trips to Annapolis. We was very well stocked, super clean and nicely Decorated. We will definitely return to this house in the future.
- Matthew
Great 2nd stay
5/5 stars
Our 2nd time staying at this property. There’s plenty of room for lounging around. Bonus: The house has tons of character!! The kitchen is excellent with very nice appliances and cookware. Our Mid loves to cook and whipped up some excellent dishes for us during our visit. Location can’t be beat. The home is within easy walking distance to restaurants, shopping and USNA. There’s plenty of off street parking which is hard to find this close to all of the downtown activities.
Awesome house !
5/5 stars
Well equipped, very clean, lots of charm and character in this home. Parking is excellent and location is close to USNA and all the downtown action.
Celebration of life weekend
5/5 stars
The house was absolutely perfect for our celebration of life weekend. The proximity to the AYC and downtown was amazing. The interior of the house is well appointed and has a ton of Annapolis charm. And of course the parking was a huge benefit. Would highly recommend and definitely stay again. Opportunities: The owner has many personal items in The house which did not bother us but should be noted. Also the backyard needed to be cleaned up (dog mess). ITrip’s was extremely easy to work with and very responsive.
- Jennifer
Stay in crabtown
4/5 stars
Great home that is well equipped and beautiful. Can’t beat the location. The neighbor behind the house does watch visitors like a hawk which felt like an invasion of privacy and reports live to the owner. I understand taking care of your place while being away but this was a new level. Just something to be careful of but still worth renting for the location and beautiful home!
- Avery
Excellent Stay
5/5 stars
We couldn't have been more happy with the house: location, rooms, porch, parking, yard were basically as great as they get downtown. 10/10 will rent this house again.
- David

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Contact Manager

Phone (410) 571-4076