The Fleet's Inn

2 BR
2.5 Baths
Sleeps 4


Stay just steps from the Annapolis waterfront! Cherished by the multi-generational Navy owners who have updated the modern home, while maintaining the charm of residing on the Historic District's Fleet Street. Enter the sunny family room decorated in full Semper Fi pageantry. Head back to the gourmet kitchen, with sleek granite counter tops, stainless steel appliances and all of the kitchen tools you'll need for your stay. Head out to the private fenced stone patio where you'll find a BBQ grill and seating for 4 under the umbrella at the table. In the hall of the main floor you'll find the powder room and full laundry room.

Head up the Navy-decorated stairway to the 2 bedrooms and 2 full baths on the second floor. The en-suite primary Bedroom has a Queen bed, flatscreen TV and a shower/tub combo. Across the hall is the guest bedroom with 2 twin beds and an en-suite full bath with stand-up shower.

When you are ready to see the sights of Annapolis, step outside on to the cobblestone street just one block to the City Dock, shops, restaurants and the Naval Academy.

SLEEPING ARRANGEMENTS 2 BR / 2.5 BA / Sleeps 4 (plus 1 more on an air mattress - available upon request):

Primary Bedroom:

- Second Floor

- Queen Bed

- Flatscreen TV

- En-Suite full bath

Twin Guest room:

- Second Floor

- Two Twin Beds

- Flatscreen TV

- Full en-suite bath


- Full gourmet kitchen with stainless steel appliances and granite countertops

- Private back brick patio with outdoor dining table for 4

- Eat-in kitchen table seats 2

- Seating for 4 at the folding table that pops up in the living

- BBQ Grill with a tank

- WiFi

- Multiple flatscreen TV's

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

- 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.

- Keyless entry. Drive straight to your rental home and enter the electronic lock code on the front door.

Property Distance to:

- U.S. Naval Academy – 1 block

- 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. 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

30 Fleet St Annapolis, MD 21401
Registration Number: STR21-144975

Sleeping Arrangements

Primary Bedroom Queen
Guest Room Twin (2)

Bathroom Configuration

Second Floor Queen: Toilet, Combo Tub Shower
Second Floor Twin: 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
Bed Linens
Big Screen TV
Carbon Monoxide Detector
Clothes Dryer
Coffee Maker
Cooking basics
Enhanced Cleaning
Full Kitchen
Hair Dryer
Historic Downtown
Ice Maker
Internet Access
Iron and Board
Living room
Open Patio
Private Backyard
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 The Fleet's Inn. 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 4 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 4 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.


Fabulous on Fleet Street
5/5 stars
This is a wonderful, fully equipped house close to everything in DTA. There was plenty of room, and it was extremely clean. Will definitely stay here again!
- Melissa
Excellent for boat show
5/5 stars
This was an excellent location for attending the Annapolis Boat Show! Within walking distance to all events, restaurants and shopping area. Perfect accommodations for 2 couples and a great little back patio to enjoy so outdoor rest!
- Jenny

Book Your Stay

Select your trip dates.
Contact Manager

Phone (410) 571-4076