The Helm on Fleet

2 BR
1.5 Baths
Sleeps 5


This well-appointed recently-renovated home in the heart of Annapolis is located just steps from both the Capitol and City Dock. Guests will enjoy the new upgrades, including the open floor plan, gourmet kitchen and new baths. The private backyard is great for those who are looking to entertain during boat show or a Navy game.

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 / 1.5 BA / Sleeps 4 adults (plus 1 more on sofa or air mattress - available upon request):

Front King Bedroom:

- Second Floor

- King Bed

- Flatscreen TV

- Private balcony

- Full bath in the Hall

Queen Bedroom with balcony:

- Second Floor

- Queen Bed

- Flatscreen TV

- Full bath in the Hall


- Full gourmet kitchen with stainless steel appliances and granite countertops

- Private back brick patio with outdoor seating

- Dining room table seats 6

- BBQ Grill

- WiFi

- Multiple flatscreen TV's

- Full size air mattress

- Travel crib and crib bedding

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

- Washer & dryer located inside the home

- Dogs allowed with a $150 non-refundable fee paid prior to checkin.

- 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. 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

24 Fleet Street Annapolis, MD 21401
Registration Number: STR-143490 Expires 4/01/24

Sleeping Arrangements

Front King Bedroom King
Balcony Queen Bedroom Queen

Bathroom Configuration

Second Floor Hall: 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
Dining room
Enhanced Cleaning
Full Kitchen
Hair Dryer
Historic Downtown
Ice Maker
Internet Access
Iron and Board
Living room
Open Patio
Pets Considered
Private Backyard
Private entrance
Self Check-In
Smoke Detector
Smoke alarms
Travel crib
Washing Machine
body wash
hot water
portable crib



Frequently Asked Questions


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


Beautiful cozy house in perfect location
5/5 stars
Stayed here for the legislative session and it met every need and then some. First off the location is truly ideal: 5 minute (or less) walk to waterfront, main st., state house, GA office buildings, west st., and more. The house itself is quite lovely. Appliances are all updated and kitchen is modern and while the house maintains that downtown Annapolis row home charm.
- Joshua

Thank you for your positive feedback, Joshua & We welcome you back anytime! Melissa~iTripAnnapolis

- Manager Response
When you don't want to leave, that's a good thing...
5/5 stars
Star Review: Five of Five. This is a special, special place. And it's distinctively Annapolis... Steeped in history, and steps away from everything which makes this waterside town which once served as the Capitol of the United States and which is older than the country, the Helm on Fleet is now one of my Top Fave short term rental homes. It's quite literally a historic house, on a historic street, in a historic district which is steps away from literally everything. The location is INSANELY good. Parking is tricky, so use a garage after you load out and don't go back to it until you load in on departure. If you need to leave the house for a restaurant or venue which is further than a water-taxi ride away, it's Uber/Lyft friendly, there are plenty of rides available, and if you don't want to cook, meal delivery service is available... but you won't really need it because you are just steps away from the most amazing restaurants you'll only find in 'Naptown. Location is everything... this is one of the best locations you can get. The house is the intersection of thoughtful preservation of history meets modern but not over the top amenities. The kitchen is great for cooking/baking/hosting friends. The back patio and yard space are inviting places to entertain. The queen bedroom balcony is the perfect place to unwind. I quite literally love this house and the location and the history. The owners have a special place here and they've done a stellar job bringing the house an infusion of modern while preserving its special DNA. I want this to be like my new weekend home when I need to get out of DC/Rockville but don't want to hike say to Hershey or Nemacolin or wherever. Tech: TV/WIFI/XFINITY is solid. If you need more Wifi-firepower, consider brining your own hotspot but I didn't need it and I did a considerable amount of involved work via this wifi over the last couple of days. Beds: Two BR. King up front on Fleet street, Queen in back overlooking back yard area/patio/fresco. Queen BR has a great balcony... perfect place to unwind and relax, chat, chill, think... breathe. Bathrooms: Upstairs shower/bath are amazingly redone and updated. Loved the H2O amenities. Felt like Disney (they used to use H20 in all the resorts). Downstairs 1/2 bath has a bit of low headroom, but I am 6'2" and I was fine. AC: Secret to this - set temp, HOLD temp, RUN program. It works great but it's a finickey UI but you'll figure it out. Or, they'll put in a Nest thermostat or something. If you need fans, check the master closet! I have absolutely ZERO bad things to say about this place. The owners have something special here. Again I love it... ... and I LOVE the management company and their proactive communication! They were ahead of me on everything and made me feel like I was the most important travel party in the world. And I mean that with no hyperbole: They over communicate and over deliver in an epic way. I was not there long enough. I can't wait to go back. PS: Thanks for the wine. PPS: Miss Shirley's. Have 'em deliver breakfast. You'll thank me later, lovers of Southern food with a lil' bit of soul. PPSS: Crabs. Alaskan King. Maryland Blue. Buddy's Crabs & Ribs: Family-owned restaurant with a raw bar and all-you-can-eat buffet on Sunday for Brunch. You are welcome. I promise. Thank you... on behalf o' me, my daughter and my GF... -tk
- Toby Knapp

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Phone (410) 571-4076