The MidshipDen

3 BR
1.5 Baths
Sleeps 6


**Flexible Commissioning Week Cancellation Policy**

This Naval Academy-themed 3 Bedroom home was just fully renovated and is ready to host Annapolis visitors! It has a twin sister next-door, The Annapolitan, that is a mirror image of the home. Both have multiple outdoor spaces: welcoming front porches, back decks overlooking nice big back yards, and parking. The main floor provides plenty of hangout space with a family room, large screen TV, dining table for 6 with a separate desk space, a full kitchen, with many new appliances, and a half bath. The second level features 3 bedrooms and a full bathroom.

*The sister properties can be rented together, depending upon availability. Please be sure to reach out to us about those opportunities for your parties of 7-12 guests!


Master Patriotic Guest room:

- Second Floor

- Queen Size Bed

Navy & Gold Guest room:

- Second Floor

- Full Size Bed

Nautical Guest room:

- Second Floor

- Queen Size Bed


- Furnished Front Porch

- New back decking

- Parking for 2 cars behind the home

- Fenced in the back yard

- Full gourmet kitchen

- Dining room table seats 6

- WiFi

- Big Screen TV

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

- Washer & dryer located inside the home

- Non-Smoking

- Dogs Allowed - $150 non-refundable deposit due per pet at the time of booking.

- Contactless entry. Drive straight to your rental home and enter the code to the back door that we will email to you prior to checkin.


Property Distance to:

- U.S. Naval Academy – 1 mile; 15 minute walk

- Washington, DC – 30 miles

- Baltimore - 25 miles


*Amenity & Supplies starter pack, coffees and sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid.

* 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 unless pet deposit has been paid prior to arrival. Please respect the neighbors and neighborhood.

Check-in time: 4:00 pm

Check-out time: 11:00 am

**If Commissioning Week is cancelled by the Naval Academy, families who book this property will receive a Full Refund.

14 Jefferson Pl Annapolis, MD 21401
Registration Number: STR24-145373

To purchase a vacation home like this one, Natalie Chamberlain with Remax Leading Edge or click here to see properties for sale.

Sleeping Arrangements

Front Queen Queen
Middle Guest room Full
Garden view Queen Queen

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 Available
Pets Considered
Private Backyard
Private entrance
Self Check-In
Smoke Detector
Smoke alarms
Washing Machine
body wash
hot water
outdoor Fireplace



Frequently Asked Questions


Tenant is at least 25 years old and will be an occupant of the unit The MidshipDen. 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. 


Cancellations must occur at least 30 days prior to arrival date, or WILL BE CHARGED THE FULL AMOUNT. If cancellation occurs 30 days or more prior to arrival date all monies will be refunded with the exception of a $100.00 administrative fee.


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


If you wish to bring your dog, you will need to pay the $150 non-refundable pet deposit per pet prior to arrival.  If you bring an unathorized pet on to the property, you will be asked to vacate immediately with no refund of rent or damage deposit. Homeowner and Agent assume no responsibility for any illness or injury that may occur to pets or humans while on the premises. Homeowner and Agent assume no responsibility for the behavior of the pet(s); that responsibility is the Tenant owner.


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 Smoking.
  6. Reservations are not made by or for a minor, defined as any person under the age of 25.
  7. 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.
  8. 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 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.


Wonderful home and location
5/5 stars
Great home and location in Annapolis! We were greeted with a super clean house with all amenities needed for your home away from home. Also, a nice treat was a bottle of wine with a few bags of crab chips! 4 of us stayed 3 nights for a USNA reunion and our stay at this location exceeded our expectations! Will definitely stay again!
- Mary
Boat Show Accommodation
4/5 stars
This was a fair accommodation for three couples. Only one full bath made it a little challenging. The walk down to the docks for the boat show was a little far for those with back stress or those not in best of health. Cost was fair for boat show weekend.
- Barbara
Close and Convenient w nice patio
5/5 stars
It was nice to sit outside in the patio and look at the fire pit 🔥 while grilling 🥩 steaks and drinking a California 🍷
- Aaron
Great Place! Clean! Walkable to Main St!
5/5 stars
This place worked out perfect for us and the pup for Memorial Day Weekend! Great location! Just the right distance to experience everything on West Street all the way down to Main St and the docks. The outdoor space is great and everything was very clean. The house was equipped with everything you need, which a lot of the items appeared to be brand new. We will for sure consider this place again for our next trip to Annapolis!
- David
Weekend Trip
5/5 stars
We decided to take a last minute trip to Annapolis. The Midship Den is a perfect place for an Annapolis weekend. The house was clean and we really liked the location. Our Mid leaves for flight school in a week and he was able to spend his last weekend with us. We would recommend the Midship Den to anyone.
- Ted
Wonderful all around
5/5 stars
This was the perfect house for our trip for parents weekend. It was close to the yard and also walking distance to a bunch of fun places to eat. The home was clean and well stocked with everything we needed to make our stay enjoyable. Will definitely be back!!
- Lauren
iTrip Review
5/5 stars
We rented the MidshipDen for Commissioning week and could not have had a better experience. The house was clean, nicely decorated and had all the amenities we needed including a fenced backyard and off-street parking. It is within walking distance of the Naval Academy, football stadium and DTA.
- Teresa
Great house, awesome location
5/5 stars
We couldn't have asked for a better place to stay for our visit to Annapolis! The MidshipDen is beautifully decorated and perfectly located in downtown Annapolis within walking distance to some of our favorite restaurants. We had all of the amenities we needed and we were very thankful for a pet-friendly house with a fenced in backyard so we could bring our 4-legged family member with us :) We will definitely be staying here again next time we're in Annapolis and I suggest you do, too!
- Brooke
Good location
5/5 stars
We enjoyed our stay at the Midshipman den. It was clean, close to downtown and we were able to walk to the Navy football game.
- Janet

Book Your Stay

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Contact Manager

Phone (410) 571-4076