Duke's Den

4 BR
4 Baths
Sleeps 14


*Flexible Commissioning Week Cancellation Policy*

Large Historic Downtown Annapolis gorgeous home with 2 parking spaces! With all the charm of an old world house, the professionally re-decorated home has all of the contemporary amenities for guests looking to experience a 5-Star luxury stay.

Enter the home from the welcoming front porch and enjoy a glass of (complimentary!) wine on the new sectional sofa on the porch. The home's stunning dining room table greets you upon entering the home. Walk through to the large family room and the spacious gourmet kitchen. The open space has plenty of seating and a flatscreen TV. The kitchen's Viking gas stove, huge granite top center island, stainless appliances, custom shelving and 2 eating areas are perfect for big family meals!

Head upstairs to the 2nd floor's 2 King Bedrooms, and 2 full baths. The master suite features a luxury spa bath with separate walk-in shower, jetted jacuzzi tub, walk-in closet with laundry and hardwood floors. The front room with a King bed has use of the large full bath in the hall. The 3rd floor has 2 more bedrooms and a full bath. The "Bunk Room" has 2 Full bed bunks (Full bed down, Twin up) with built-in reading lights and charging stations next to each bed. Guests using the Queen bed in the 3rd floor guest room will enjoy the natural light and views of the historic Annapolis city street. Head down to the lower level to another oversized family room with another flatscreen TV, Queen size pullout sofa in the adjacent den and half bath.

Walk to restaurants, shopping, concerts, water activities, and the The United States Naval Academy!

**COVID - 19 Extra Special Precautions: Our guests' and staff's health is our top priority. Our cleaners are taking every precaution when cleaning this home and making sure it meets CDC standards. We are going above and beyond to ensure all surfaces and touch points are being cleaned thoroughly and disinfected (including all light switches, faucets, doorknobs, cabinet handles, remotes, etc.). You will have self check-in and no physical interaction with anyone.**

Be sure to ask about discounted rates for extended stays.

SLEEPING ARRANGEMENTS 4 BR / 3 full Bath; 2 half baths / Sleeps 12:

Master Bedroom:

- Second Floor

- King Bed

- En-suite luxury bath with both Jacuzzi tub and stand-up shower

- Oversized walk-in closet with washer/dryer

- Flatscreen TV

Second Floor Front King Bedroom:

- Flatscreen TV

- Full Bath in the Hall with dual vanity and bath/shower combo

Third Floor Bunk Room :

- Two sets of twin beds over full beds

- Full Bath in the Hall

Third Floor Queen Guest Room:

- Flatscreen TV

- Full Bath in the Hall

Lower Level Den

- Separate from the lower level family room

- Queen Pullout sofa

- Powder Room


- Front Porch with sitting area with brand new furniture

- Dining Room table seats 8

- Spacious gourmet kitchen

- Kitchen counters seats another 6

- WiFi

- Big Screen Smart TV's

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

- Parking for 2 cars

- Washer & dryer located inside the home

- Non-Smoking

- No pets

- 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 back door with an electronic lock code. Prior to your visit, we will send you our mobile app with directions and full instructions.


Property Distance to:

- U.S. Naval Academy – 4 blocks

- Washington, DC – 30 miles

- Baltimore - 25 miles


* Guest Gift Basket!

* Amenity & Supplies pack, a starter set of 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

*If the Naval Academy cancels Commissioning Week events, guests will receive a full refund.**

190 Duke of Gloucester St Annapolis, MD 21401
Registration Number: 145031

To purchase a vacation home like this one, Shane Hall with Compass Realty or click here to see properties for sale.

Sleeping Arrangements

Master Bedroom King
2nd Floor King Guest Room King
Bunk Room Bunk Full (2)
3rd Floor Queen Guest room Queen
Basement Den Sofa Queen

Property Rules

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


Air Conditioning
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 Available
Private entrance
Self Check-In
Smoke Detector
Smoke alarms
Washing Machine
body wash
hot water



Frequently Asked Questions


Tenant is at least 25 years old (an "adult") and will be an occupant of the unit Duke's Den. 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. 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 14 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.
  9. All noise must be brought inside by 10pm. Failure to do so could result in a $500 fine.


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 14 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.


Annapolis Birthday Fun
5/5 stars
Keeping up with Family birthday traditions are tough when you live far away but, so thankful for Dukes Den. Wonderful family gathering spot. The kitchen was a chefs dream. I made homemade chicken arroz caldo and other mid favorite foods. When we took to the streets it was the best location to bars and restaurants. The parking is a life saver. The house was so warm with spaces to catch up without ever feeling crowded. Cathy as usual was responsive and quick! The beds and bathrooms were well appointed. This house is a must stay in Annapolis!
- Vivian

Thank you for allowing us to host your stay Vivian & for providing this positive feedback! We welcome you back anytime! Melissa~iTripAnnapolis

- Manager Response
Duke’s Den
5/5 stars
We loved our stay at Duke’s Den in Annapolis. The house is wonderful, well appointed, fabulous location. Would highly recommend!!
- Angela
Lovely and close to everything!
5/5 stars
We loved staying at Duke’s Den over the weekend for a family wedding. We were able to walk to the church, the reception site, the rehearsal dinner, and all the shopping and restaurants! The house was super clean and well appointed. There was plenty of room for everyone to spread out. I definitely recommend. .
- Beth
Nice and Clean and Oh So Convenient!
5/5 stars
Duke’s Den was a great house for our family. We came for my brother’s wedding in downtown Annapolis, and it was so easy to just walk to all of the wedding related events, to go out to eat, to the playground, etc. The house was spacious and clean, and the beds were super comfortable. We would definitely stay there again! I think the location and the kitchen were my favorite features of the house, but we have zero complaints and we loved it all!
- Sarah
Awesome Home
4/5 stars
The home is really well thought out and equipped - with exceptional space. The location is perfect and the two car off street parking is essential! It is unfortunate that the beds are so soft -not sure if this is intentional or not. Some of us were not able to sleep well… otherwise it would be 5 star review.
- Douglas
Thank you- Everything was Perfect!
5/5 stars
We stayed at Duke's Den for our daughter's wedding weekend. Everything went smoothly from check in to check out. The team thought of everything including a welcome note and starter amenities in the kitchen and bathrooms. The home is larger than it appears in the photos. We were impressed from the moment we walked in. The house is clean and beautifully decorated with amazing attention to details. It truly felt like home for the weekend. The kitchen and dining room allowed us to have extended family over for breakfast and lunch. Walking distance to restaurants, the Naval Academy and waterfront. We will stay here again on future trips to Annapolis.
- Lisa
Bachelorette Weekend!
5/5 stars
This was the perfect house for 8 ladies looking to have a great long weekend to celebrate a friend's upcoming nuptials! The location is ideal for walking to restaurants, shops and the harbor. We enjoyed a couple nights in cooking dinner in the spacious kitchen that was well-equipped for cooking and entertaining. The bedrooms were extremely comfortable and decorated perfectly. We're even talking about going again for another weekend to have a reunion!
- Kimberly
Duke's Den
5/5 stars
A fanastic property with parking & in a good location to walk to the shops and restaurants. The house was clean, stocked with essentials and decorated nicely. An enjoyable weekend! Thank you!
- Dinah

Book Your Stay

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Contact Manager

Phone (410) 571-4076