The Port

2 BR
1 Bath
Sleeps 5


**Flexible Commissioning Week Cancellation Policy**

The Port is situated in the heart of Eastport’s charm, mere steps from countless pubs & restaurants along “Restaurant Row” and within walking distance to the Waterfront bridge. The Port retreat is located on the second level of the property and offers a newly renovated suite that accommodates one to four people comfortably with its own private staircase to the entrance and free, on-street parking.

This unit offers an open floor plan with plenty of natural sunlight, a private master bedroom with queen-sized bed and balcony overlooking the back yard, all new stainless-steel appliances and breakfast bar in kitchen, a dining area for six, office nook, living area complete with convertible sofa & television and quaint private loft area with futon. One full bathroom, WIFI, Central AC/Heat, and Washer & Dryer.

In addition to the vicinity of restaurants, The Port Retreat is also a short walk to museums, a local beach, or a water taxi ride over to Historic Downtown Annapolis and the United States Naval Academy. Please note that while we are pet friendly we do not have access to the yard behind the port. It belongs to the tenant below. There is a sign to remind guests.

**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.


Queen Bedroom:

- Luxury Queen Size Bed

- Full Bath in the Hall


- Queen Size Sleeper Sofa


-Fun for the kids with a Queen futon


- Full gourmet kitchen

- Dining room table seats 4

- Loft with Futon

- WiFi

- Big Screen TV

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

- Washer & dryer located inside the home

- Non-Smoking

- Pet-Friendly: Please note that while we are pet friendly we do not have access to the yard behind the port. It belongs to the tenant below. There is a sign to remind guests. This includes pet usage.

- While this property does not have attached parking, the street has parking available most times of the year.

- 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 walk up to the 2nd level and enter the 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 – 1.5 miles

- Washington, DC – 30 miles

- Baltimore - 25 miles


* Welcome basket with wine, chips, coffee and creamers for every guest at check-in.

* 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. Please remember No Pets allowed at this home unless you have paid the $150 Non-refundable pet deposit per pet . 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 Commissioning Week is cancelled by the Naval Academy, families who book this property will receive a Full Refund.

413 Fourth Street, 2nd Floor Annapolis, MD 21403
Registration Number: 144281

To purchase a vacation apartment like this one, Marshall Tracy E with Berkshire Hathaway HomeServices PenFed or click here to see properties for sale.

Sleeping Arrangements

Bedroom Queen
Living Room Sofa Queen
Office/Loft Sofa Queen

Property Rules

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


Air Conditioning
Bed Linens
Big Screen TV
Carbon Monoxide Detector
Clothes Dryer
Coffee Maker
Cooking basics
Dining room
Enhanced Cleaning
Full Kitchen
Hair Dryer
Ice Maker
Internet Access
Iron and Board
Living room
Open Patio
Parking Available
Pets Considered
Private entrance
Smoke Detector
Smoke alarms
Washing Machine
body wash
hot water



Frequently Asked Questions


Tenant is at least 25 years old and will be an occupant of the unit The Port. 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. 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 5 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 5 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.


Plebe parents weekend
5/5 stars
Great place to stay. Very quiet neighborhood. Short walk to the Academy and DTA.
- Daniel
Great Spot!
5/5 stars
The Port is a lovely spot for weekenders to enjoy the best of Annapolis!! Walking distance to everything, steps from Annapolis’ finest cuisine, and nestled right in the heart of all of Annapolis’ charm. Cathy, Sean, and Jennifer with Itrip went well above and beyond to make everything perfect for me. Absolutely wonderful concierge that went out of their way. I definitely recommend I Trip and The Port to anyone who wants to enjoy this charming city.
- Karina
Perfect location
5/5 stars
This upstairs apartment is in the perfect location for everything in Annapolis. To get to downtown Annapolis, it's just a short walk over the bridge. There are also a lot of great places in eastport to eat and shop. The apartment itself was perfectly appointed and my kids loved sleeping in the loft upstairs. My husband and I loved the back porch off of the bedroom as well. Plenty of room for our family of 4 plus our pups.
- Sarah

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Contact Manager

Phone (410) 571-4076