Eastport Gem

3 BR
3 Baths
Sleeps 8


*Flexible Commissioning Week Cancellation Policy*

This unique 3 Bedroom/3 Bath home is located in Eastport - next door to Bakers and Co. bakery and coffee shop - in a self-contained rear section of a single family home. After parking in the 2-private off-street spaces, walk through the large private backyard with lounge chairs, a dining table for 6, and an outdoor fireplace. Enjoy the complimentary bottle of wine around the outdoor fireplace upon your arrival.

The main door opens into the restaurant-style open kitchen with all high-end appliances, dining and family rooms. Head downstairs to the gaming den with flatscreen TVs, an air hockey table, foosball table, bar, a living room with a pullout sofa and a full bath. Upstairs on the 3rd floor are 3 bedrooms and 2 more full baths. The King bedroom with an en-suite bath opens out to the balcony overlooking the backyard. The balcony goes across the back of the home connecting to the Queen Bedroom. The Queen and Full bedroom share a full bath in the hall.

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.


King Suite:

-Second Floor

-King Bed

-Full en-suite bath

Queen guest room:

-Second Floor

-Queen bed

-Full bath in the Hall

Double 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


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

-Lower level multi-room gaming den

-Dining room table seats 6

-Kitchen bar seats 4

-Large outdoor lounging and dining space

-Outdoor fireplace (BYO 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 TV

-Luxury bed and bath linens, complimentary toiletries

-Starter Kit, and boutique-level service

-Full-sized washer & dryer

-Coffee maker 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

Upstairs Suite King
Queen Bedroom Queen
Full Bedroom Full
Game Room Sofa Full

Bathroom Configuration

Second Floor King: Shower, Toilet
Second Floor Hall: Toilet, Combo Tub Shower
Lower Level: Shower, 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
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 Gem. 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 8 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 8 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.


Good location - big kitchen - dog friendly
4/5 stars
Pros - cool house for a family party - great pro kitchen and big eating area, game room, and big yard with fireplace. Full linens and towels on arrival was really convenient. *Dog Friendly* Cons: very uncomfortable furniture - you really can’t sit and hang out. King bed mattress was bad, and all pillows were awful. Ok for a short trip but we didn’t get much sleep. Bring your own pillow.
- George
Awesome stay
5/5 stars
Long weekend trip was great!
- Ryan
Fantastic place!
5/5 stars
Beautiful and spacious place that my entire family enjoyed. So close to bustling downtown Annapolis and amazing amenities. Would definitely recommend and would love to stay again the next time we happen to be in town.
- Nick
Definitely a Gem!
5/5 stars
We enjoyed an amazing weekend at the this Eastport gem! Our family of five, which included kids ages 12, 9 and 4 loved the house, and all of the accommodations were wonderful and suited all of our needs. What a fun, unique house with all the amenities needed for a weekend stay in Annapolis! We enjoyed many short walks to the Naval Academy and City Dock. We appreciated the ease of check-in and the rooms that were move-in ready. If you’re looking for a funky, beautiful, home with cool vibes and within walking distance to Downtown Annapolis, look no further.
- Alison
All was great!
5/5 stars
Our stay at the Eastport Gem was amazing!! The home was lovely, well- decorated, and fully-stocked!! And the hosts were very accommodating and responsive - We didn’t have any problems during our stay, but they answered a few questions in advance of our arrival. Highly recommend!
- Mid parents from TN

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Contact Manager

Phone (410) 571-4076