Jackson Bunker

3 BR
2 Baths
Sleeps 12


Located in the Annapolis "Republic of Eastport", this charming pet-friendly home is a short walk to restaurants, shops, the waterfront and Truxton Park. The 3 bedroom, 2 bath home has recently been renovated and has plenty of space and beds for 2 families traveling together or a large extended family. The first floor has a Queen bed, full bath and room for 2 more on the pullout sofa in the Family room. Head out to the beautiful fenced-in backyard with a deck to enjoy your (complimentary) morning coffee. There is a furnished covered living space out in the backyard to enjoy a (complimentary) glass of wine upon your arrival.

Head back in the house and up the stairs to the 2 bedrooms, den and full bath in the hall. The first guest room has a Queen bed, the second has a full and 2 twin beds and the den has a futon sofa that sleeps 1 adult comfortably or 2 small children.

There is free and unrestricted street parking in Eastport. A one mile walk, bike ride or drive will bring you to downtown Annapolis, where you’ll find Main Street shops, more restaurants, bars and the beautiful Ego Alley! This home is wonderful for families and friends coming in for that special Naval Academy or boat show event, or wanting to take in the sights and sounds of Greater Annapolis.

SLEEPING ARRANGEMENTS 3 BR/2 BA / Sleeps 10 adults or 8 adults and 4 children/teens:

Main Floor En-Suite Queen Bedroom:

-Queen Bed

-Full Bath

Main Floor Family Room

-Queen sofa bed

-Desk and desk chair

-Full bath in the hall

Queen Guest room

-Queen bed

-2nd Floor

-Full bath in the hall

Upstairs Guest room

-Full Bed and 2 Twin beds

-Full bath in the hall

Upstairs Den

-Full Futon

-Full bath in the hall


-Full kitchen

-Dining table seats 4

-Private fenced backyard

-Back deck and covered furnished living space

-BBQ grill (propane included)

-High Speed Internet and WiFi

-Big Screen Smart TV.

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

-Un-restricted street parking

-Full-sized washer & dryer located inside the home

-No smoking

-Dogs Allowed with Non-refundable $150 deposit per pet.

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

Property Distance to:

-Downtown Annapolis – 1.6 miles

-U.S. Naval Academy – 1.6 miles

-Washington, DC – 39 miles

-Baltimore - 31 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 made 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 pets unless the $150 non-refundable pet deposit has been paid prior to checkin. Be respectful of the house and contents - it is someone's home and the owners do come back from time to time to stay in their property. 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

1016 Jackson Street Annapolis, MD 21403
Registration Number: STR22-145201

Sleeping Arrangements

Main Floor Queen Queen
Upstairs Queen Guest room Queen
Upstairs Guest Room 2 Full, Twin (2)
Upstairs Den Room Sofa Full
Family Room Sofa 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
Pets Considered
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 and will be an occupant of the unit Jackson Bunker. 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 12 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 12 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.


Fair but pricey
3/5 stars
The property was the perfect location for our trip and needs. The issues we had were: 1. The couch and rug in the living room were not clean and were covered in pet hair. 2. There was no place to park. We knew the people across the street so were able to park in their driveway. There was a Livewell pickup truck parked in front of the house the entire week and it never moved. Apparently the driver of this truck does not live on Jackson St.. This would be an issue for other guests who don’t have other parking options. Otherwise our needs were met but the price was expensive for the quality of property.
- Jennifer
Nap Town Escape
5/5 stars
We came down to Annapolis for yacht week/bachelor party and the house was a great home base for the whole gang. The house was in a good location as it was either an easy car ride/uber or we would make the 1.4 mile walk to downtown. There was easy street parking upon arrival. We had lots of room for everyone to sleep due to the sofa beds. The sectional in the living room was home to lots of great games and conversation. The house has a private back yard with good deck furniture for use. We would definitely recommend Jackson Bunker for a group visiting the Annapolis/Eastport area!
- Timothy
Best spot for our little Renn Faire weekend!
5/5 stars
Our stay was wonderful and cozy, property was exactly as described. We enjoyed our stay and it is conveniently located near all the things in Annapolis. Would recommend to anyone visiting the area.
- Janelleen
Clean and inviting home
5/5 stars
Overall our 3 day stay was very pleasant. There were plenty of towels, toilet paper and other essentials for all guest to use. Everything was set-up and prepared for our stay including a complementary bottle of wine. The backyard is quite the place to just sit relax and talk with your friends. Over all I would give this place a 5 out of 5. We did have one minor inconvenience when checking in, and that was that the digital lock was not working. No matter how many times we tried the code it didn’t work. ITrip worked with me relentlessly to get the issue solved as quickly as possible. Overall great customer service as well!
- Craig
Perfect Getaway house in Annapolis
5/5 stars
This home is so cozy and perfect for any family or gathering! They have taken an old house and turned it into a cute and well furnished home away from home. Only 1.3 miles away from downtown. Easy to find, well maintained, and great amenities. Definitely would recommend for your stay in Annapolis
- Hannah

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Contact Manager

Phone (410) 571-4076