The Annapolitan

3 BR
1.5 Baths
Sleeps 6


This Annapolis-themed 3 Bedroom home now has a new hot tub! It has a twin sister next-door, The MidshipDen, and is a mirror image of the home. Both have multiple outdoor spaces: welcoming front porches, with a back decks overlooking nice fenced-in back yards, and parking. There is also a 3rd deck in the backyard. 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 Red Bedroom:

- Second Floor

- Queen Size Bed

Yellow Guestroom:

- Second Floor

- Full Size Bed

Black and Red Guest Bedroom:

-Second Floor

-Full Size Bed


- Furnished Front Porch

- New back decking on 2 new decks in the fenced-in backyard

- Hot tub in the backyard

- Parking for 2 cars behind the home

- 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 at the time of booking.

- Contactless entry. Drive straight to your rental home and enter using the code we will send 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. Dogs allowed if pet fee of $150 is paid prior to check-in. 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

16 Jefferson Place Annapolis, MD 21401
Registration Number: STR24-145372

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

Sleeping Arrangements

Master Red Bedroom Queen
Yellow Guestroom Full
Black and Red Guest Bedroom: Full

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
Hot Tub
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 Annapolitan. 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.


USNA visit
5/5 stars
This was my first stay at the Annapolatin. We had a wonderful stay. The home was very clean, cozy, and stocked with all the essentials needed for a weekend visit with my mid. The location is great and had convenient parking.
- Jill
Another great stay!
5/5 stars
We had another great stay with iTrips service and support on our trip to Annapolis. Home was spacious, clean, and well cared for. Great location — walked to USNA, downtown Annapolis, and the Stadium … all with ease. We’ll be back!
- Karie
Perfect place and location
5/5 stars
The house was perfect and in an amazing location. It had everything we needed. We can’t wait to come back on our next visit to Annapolis.
- Michele
Wonderful Getaway to Annapolis
5/5 stars
We loved our stay at the Annapolitan. The house was a wonderful fit for our family of 5. Kitchen was stocked with everything we needed, and we enjoyed making meals and making ourselves at home. My husband spent the first day working at the desk, and the wifi was great! We enjoyed watching movies and playing some of the fun games in the house. At night, we loved having a yard for the kids to run around and the fire pit! The beds were comfy. The house is great for a family trip or even a group trip. The house is perfectly located to enjoy Annapolis. We spent our days walking through the city to the waterfront, Naval Academy and Newman Street Playground. I personally loved running the city. We enjoyed coffee at Curate which is very close to the rental. We will definitely be planning a trip back to Annapolitan.
- Ashley & Greg
USNA Commissioning Week
5/5 stars
We truly enjoyed our time at the Annapolitan home. It is a quaint home, perfect for the town of Annapolis. It has all the amenities a family would need to enjoy this comfortable home. The Annapolitan is with walking distance of shops and restaurants, and the US Naval Academy. It is clean and stocked with all the essentials. We were grateful to Sean and Jenn for the housewarming charcuterie board, champagne and graduation gift for our midshipman. Their thoughtfulness carries throughout this fine home and helped make our stay so memorable.
- Maureen
Spring Break
5/5 stars
My husband, daughter, mini- Goldendoodle and I LOVED our stay at 16 Jefferson Pl! The house is perfectly clean, comfortable and homey, yet it has sincere, sweet historical charm!! It’s a 5 minute drive to downtown Annapolis! We always love the food and energy of the dock and downtown area!! Ollie, our pup, loved the fenced-in backyard and meeting the neighbor dogs!! We genuinely appreciate Sean checking on us to ensure our stay was wonderful!! It absolutely was!!! Thank you for a restful and beautiful Spring Break trip!!
- Stephanie

Book Your Stay

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Contact Manager

Phone (410) 571-4076