Eastport Retreat

6 BR
5.5 Baths
Sleeps 14


*Flexible Commissioning Week Cancellation Policy*

This unique home was originally built in 1927, and has been fully restored by the current owners. There is the classic "Bungalow" side with historic charm includes and a 2nd side, the "Gem". Both sides can be booked together to create a "Retreat" with a total of 6 bedrooms and 5.5 bathrooms. The front "Bungalow" has three bedrooms, beds for 7, 2 and a half baths, three flat panel TV's (with Netflix, of course), a bluetooth stereo system, computer with printer, Wi-Fi, washer and dryer, refrigerator, sink and microwave (a kitchenette). The Gem side has a full gourmet kitchen, 3 bedrooms, 3 full baths and sleeps 8. There is parking for 2 cars in the back of the home and a spectacular furnished private backyard with lounge chairs around the fireplace, a gas grill and a large gathering dining table.

A 10 minute walk to the 6th Street drawbridge and to downtown historic Annapolis. Walk to boat show, Naval Academy, shopping, dining - all Annapolis has to offer.

**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.


Back Part of House

King Suite:

-Second Floor

-King Bed

-Full en-suite bath

Queen guest room:

-Second Floor

-Queen bed

-Full bath in the Hall

3rd guest room

-Second Floor

-Full bed

-Full bath in the Hall

Lower Level Den

-Full sleeper-sofa (only comfortable for one)

-Floor Mattress

-Full bath

Front part of the house

King Suite:

-Second Floor

-King Bed

-Full en-suite bath

Queen guest room:

-Main Floor

-Queen bed

-Full bath in the Hall

Guest room/office

-Main Floor

-Twin Bed Daybed and Trundle Twin bed

-Desk with computer and printer

-Full bath in the Hall

Kitchenette Lounge

-Twin Futon


-Gorgeous, gourmet kitchen with high-end appliances, a pizza oven, bar-grade ice maker, 6-burner stove and 2 dishwashers and kitchenette

-Lower level multi-room gaming den

-Dining room table seats 6

-Kitchen bar seats 4

-Large outdoor lounging and dining space

-Outdoor fireplace with supplied firewood

-Gas Grill

-Balcony off back stretching across both the King and Queen bedrooms

-Private Driveway with room for 2 cars; additional non-restricted street parking.

-High Speed Internet (1 gig fios internet) and WiFi

-Flat Screen TVs

-Luxury bed and bath linens, complimentary toiletries

-Starter Kit, and boutique-level service

-Full-sized washer & dryer

-2 Coffee makers with starter kit of coffees and creamers


-Dogs allowed with $150 non-refundable pet fee per pet paid prior to check-in.

-Keyless entry. Drive straight to your rental home and enter the back 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:

-Downtown Annapolis – .6 miles (3 mins)

-U.S. Naval Academy – .9 mile (5 mins)

-Washington, DC – 32 miles

-Baltimore - 30 miles


* Welcome gift with wine and snacks.

* 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 in the baths.

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

433 Burnside St Annapolis, MD 21403
Registration Number: STR23-145327

Sleeping Arrangements

Back King Suite King
Back Queen Bedroom Queen
Back Full Bedroom Full
Recreation Room Sofa Full
Front King Suite King
Front Queen Queen
Front Office Bedroom Twin, Twin XL
Kitchenette Lounge Sofa Twin

Bathroom Configuration

Second Floor King Back: Shower, Toilet
Second Floor Hall: Toilet, Combo Tub Shower
Lower Level Den: Shower, Toilet
Second Floor King Front: Shower, Toilet
Main 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
Covered Patio
Dedicated work space
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
outdoor Fireplace



Frequently Asked Questions


Tenant is at least 25 years old and will be an occupant of the unit Eastport Retreat. 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 14 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 14 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.


Great stay!
5/5 stars
We had such a wonderful time at this house. Everyone who came remarked on how beautiful and well laid out the house was! There were plenty of linens and kitchen supplies for our group of 10. And a great location in easy walking distance from downtown while still being in a quiet neighborhood. Made for a wonderful 40th bday weekend.
- Kristine
Excellent House and Location
4/5 stars
We came down for a wedding event. 13 adults were able to fit comfortably and hang out at the house. Really neat layout of the houses and beds/baths. Great open kitchen and living room. Outdoors was pleasant and spacious to hang out in.
- Tyler
Amazing Weekend
5/5 stars
I am OBSESSED with Eastport and knew for my wedding weekend I would like to get ready in one of the neighborhood's charming homes. This house did not disappoint! We booked the entire Eastport retreat for me, my husband, and our families to stay at for our wedding weekend. The house was absolutely incredible, all the way down to the amazing decorations of old telephones, typewriters, and sewing machines throughout! You can tell the homeowners take a lot of pride in their home. The house was very clean, packed with everything we needed, and was everything we could have hoped for. The property managers were very easy to communicate with and even let us check in a little early! We will never forget the memories we made in this home and hope to rent it again in the future!
- Jillian
Eastport Gem
5/5 stars
This house truly is a Gem! I highly recommend this home to create memories and enjoy your midshipman with family. The location was perfect. The kitchen was well stocked and ready to cook some great meals. Eastport always feels a little far from the yard for me but, this location was very doable if you and your family are fit walkers.
- Vivian

Book Your Stay

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Contact Manager

Phone (410) 571-4076