Captain’s Crossing

3 BR
2 Baths
Sleeps 6


Welcome to this mid-century modern, Cape Cod in West Annapolis. This "Ralph-Lauren Cottage" exudes that "Annapolitan feel", from its original oak floors to the welcoming living/dining room great room. There is a first floor guest suite with a King bed, full bath, flat screen TV and private exit to the furnished deck and private, treed backyard.

Head upstairs to the 2 bedrooms and full bath. The spacious first bedroom has a King bed, desk and a full bath to share with the 2nd bedroom. The 2nd guest room upstairs is across the hall and has a fluffy Queen bed. A few blocks away, on Tucker St, enjoy scenic water views, launch your kayak, or power boat. Bike, walk, or sight see through the quaint shops of West Annapolis, the Navy-Marine Corps Memorial Stadium, downtown Annapolis, Ego Alley, Naval Academy.


1st Floor Suite:

- King Bed

- En Suite Full Bath with bathtub/shower combo

- Flat screen TV

- Private exit to back deck and yard

2nd Floor King Guest room:

- King Bed

- Desk and chair

- Flatscreen TV

- Full Bath with stand-up shower

Queen Guestroom:

- Queen Bed

- 2nd floor

- Full Bath right inside the King bedroom across the hall


- Big back deck

- Parking for multiple cars on the parking pad and street

- Private back yard

- Propane BBQ grill

- Full gourmet kitchen

- Dining room table seats 6

- WiFi

- 3 Flatscreen TVs

- Washer/dryer in the home

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

- Contactless entry. Drive straight to your rental home and enter using a door code we will email you. Prior to your visit, we will send you an electronic code for the lock.

Property Distance to:

- Navy-Marine Corps Memorial Stadium - .7 miles

- U.S. Naval Academy – 1.5 miles

- Washington, DC – 30 miles

- Baltimore - 30 miles

* Amenity & Supplies starter pack, coffee and sweeteners, 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 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

109 Old Crossing Ln Annapolis, MD 21401
Registration Number: STR22-145080

Sleeping Arrangements

1st Floor Suite King
2nd Floor King King
2nd Floor 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
Ice Maker
Internet Access
Iron and Board
Living room
Open Patio
Parking Available
Private Backyard
Private entrance
Screened Patio
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 Captain’s Crossing. 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. 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 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 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.


Capt’s Crossing
5/5 stars
Great house to stay in during visit to Annapolis. West Annapolis a neat area and close to stadium. Easy access to downtown and mall area as well. Overall nice amenities and comfort. Thank you!
- Robert
Highly recommend!
5/5 stars
This house was great and it was incredibly clean!!! The place was spacious enough for us (parents with two grown adult children) to have a room to claim as ours, but cozy enough that it provided the intimacy we desired. The start up toiletries and kitchen/laundry samples were a nice touch. Very close to the USNA and DTA, easy to find, easy to get to the grocery/highway/local attractions. Would highly recommend it and will stay there again when we travel.
- Kathy

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Contact Manager

Phone (410) 571-4076