Top 10% of guest reviews in this areaTop 10% of guest reviews in this area
2 bedrooms2 bathroomsSleeps 5
Popular amenities
Private pool
Onsite parking available
Kitchen
Washing machine
Air-conditioning
Barbecue grill
Explore the area
Annapolis, MD
Annapolis Harbor
Place, Annapolis Harbor
2 min walk
Annapolis Maritime Museum
Place, Annapolis Maritime Museum
6 min walk
U.S. Naval Academy
Place, U.S. Naval Academy
19 min walk
Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
40 min drive
Rooms & beds
2 bedrooms (sleeps 5)
Guest bedroom, queen size bed, work station, sitting area, and closet
1 Queen Bed
Living room
1 Single Sofa Bed
Primary Bedroom
1 King Bed
2 bathrooms
Downstairs Bathroom
Toilet · Shower only
Upstairs Bathroom
Toilet · Shower only
Spaces
Deck or patio
Porch or lanai
Kitchen
Outdoor play area
Garden
Dining area
About this property
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
421 Irie City Of Annapolis License Number 145052 Commission weeks: 2025, 2026, 2027 are booked. SORRY!! GO Navy!! Celebrating, I offer personal chef services!!!
NOTE: I LOVE my neighbors!! Please respect them. Quite times including outside pool area 9:00pm-7:30 am and a new wee one next door. :)
Irie ~ to be at total peace with your current state of being..... AKA NO WORRIES!!!!
This charming, 2 story COTTAGE was Inspired by sun-drenched island vacations and tropical shores.... ahhhh ..... The feeling of Irie!!!
This 2 bedroom and 2 full bath maybe compact, (twin size Crate and Barrel sleeper chair and Half for additional guest), BUT She SURE packs a powerful punch!! TOTALLY open concept living area, caterers stocked kitchen (I’m a former catering company owner for 20 years, just trying to simplify), fully fenced in professionally landscaped yard with SO many colorful flowers, herbs and vegetables for the picking, functional and cute sunroom for additional living space amongst nature, endless entertaining, upstairs deck off of primary bedroom ... OFF STREET PARKING and Private FULL size .... YES... PRIVATE... pool in the heart of Eastport!
Located in The Maritime Republic of Eastport, an easy going, Chill-Laxing community, 421 Irie is less then: 1 mile from Downtown Annapolis City Dock 1.2 miles from Maryland State House 1.3 Miles from the Navel Academy!!
421 IRIE offers you and your guests, up to five, everything!! Restaurant Row with over a dozen fabulous restaurants with-in a mile, small mom and pop shops, several yacht clubs and marinas, museums, and of course.... WATER Activities!! You say, you're on vacation and just want to chillax, just stay in and simply enjoy your new vacation home!!
421 Irie has it all!!!!!
Start your day off with your morning beverage from the built-in beverage and breakfast nook. Savior your authentic French pastry from our local bakery, Bakers and Co., a short stroll away. Enjoy your sweet or savory fare in the sunroom. If you must check in with work, we have an Ethan Allen secretary's desk off to itself.
Following breakfast you may choose to take a 10 minute stroll across Spa Creek Bridge to downtown Annapolis, City Dock, and the Navel Academy!! While in route, take time to admire the diverse number of power and sail boats in the numerous area marinas. ALL ... with-in a 10 minute stroll!!
You say you do not feel like walking, the best kept secret, Annapolis Water Taxi picks up and drops off only a block away!!!! $4-$9!!! It will drop you off right at City Dock!! Want to try your hand at sailing or power boats??!! There are several sailing and boating schools, YES, all with-in a 10 minute stroll!!
Once you return from your adventure to this amazing 2 story cottage, relax by the glistening saltwater pool in one of the sun loungers. Or take a dip to refresh and reset the mind. You do not feel like swimming?? No PROBLEM!! Enjoy an adult beverage in the new (Apr. 2023) sunroom while listening to some island music, reading a book, marveling at the flower garden, watching your family or friend enjoy the pool... After all, your life is IRIE when you stay with us!!
P.S. IF, you do not feel like going out to dinner or cooking, for an additional fee, there are local grab and go culinary offerings, private chefs, and curbside pickup and deliveries available.
Being a local, myself, I can give you a locals eye into activities and services, as well! There are quite a few adventure waiting for you, your family and friends at 421 Irie!
We look forward to hosting you and your guests and making everyone’s life IRIE!!!, at least for your stay!!
Cheers!!! Liz Hopkinson
Our prices include all fees. No hidden fees.
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The host requires you to complete the following before checking out:
Load and start the dishwasher
Strip any used beds and gather used towels
Remove personal items, remove leftover food and drinks and take out the rubbish
Turn off the lights, lock the doors and return the keys
Please place dirty towels and linens in laundry basket (in linen closet) and place basket on front porch.
Thank you!
Make sure to replace keys. There will be a $250 charge if keys are not replaced.
Failure to complete these may result in a negative review from the host.
1. ANY commissioning / graduation week (May) for the Navy MUST be verbally approved from myself, the owner, before ANY accepting bookings.
Power / Sail Boat Show dates weeks, must be verbally approved by myself, the owner before it is confirmed as a booking, Including instant bookings.
. No outside loud noise after 10 pm. I LOVE and RESPECT my neighbors. Please do the same!!
Important information
Optional extras
Fee for local cuisine breakfast: approximately USD 12.00 to 18.00 per person
Credit card charges are subject to a surcharge of 3 per cent
The above list may not be comprehensive. Fees and deposits may not include tax and are subject to change.
You need to know
Property Registration Number 2280460
Property # 2280460vb
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.
This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
This property accepts credit cards, debit cards and mobile payments; cash is not accepted
Mobile payment options include: PayPal
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
About the area
Annapolis
Located on a river, this holiday home is in Eastport, a neighbourhood in Annapolis. Annapolis Maritime Museum and The Colonial Players are cultural highlights, and some of the area's landmarks include Kunta Kinte Plaque & Alex Haley Memorial and John Smith House. French Soldiers Monument and Maryland Hall for Creative Arts are also worth visiting. Jet skiing and kayaking offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling and ecotours nearby.
Baltimore Washington International Airport (BWI) - 45 min drive
Restaurants
Carrol's Creek Cafe - 4 min walk
The Choptank - 15 min walk
Boatyard Bar & Grill - 3 min walk
O'Brien's Oyster Bar & Seafood Tavern - 17 min walk
Annapolis Market House - 16 min walk
Frequently asked questions
Does 421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking! have a pool?
Yes, this property has an outdoor pool.
How much does it cost to stay at 421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!?
As of 10 May 2026, prices found for a 1-night stay for 2 adults at 421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking! on 8 Sept 2026 start from £458, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
Is 421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking! pet-friendly?
No, pets are not allowed at this property.
How much is parking at 421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!?
On-site parking is available at the property.
What time is check-in at 421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!?
Check-in begins at 3:00 PM.
What time is check-out at 421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!?
Checkout is at 11:30 AM.
Where is 421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking! located?
Located in Eastport, this holiday home is within 1 mi (2 km) of Annapolis Harbor and U.S. Naval Academy. Annapolis Maritime Museum and Spa Creek are also within 10 minutes.
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
This property is absolutely amazing. The attention to detail is outstanding. The host was such a pleasure to communicate with. I will absolutely stay here again and recommend to Everyone! The location was a dream and the off street parking made things so much easier. I can’t stress enough how wonderful this experience was
Everything about the cottage was exactly as described. It’s a beautiful, well maintained space in the heart of Eastport. Such a great location within walking distance to a number of restaurants. I so appreciated the extra touches from our host!
Kimberly D.
Stayed 2 nights in Mar 2026
Response from VrboOwner on 24 Mar 2026
Hi!!
Thank you SO much. Little touches make stays a little nicer!! Thank you!!
Liz
We had a wonderful stay. The house was spotless and had everything we needed for a comfortable visit. Our favorite spot was definitely the sunporch—it was the perfect place to relax and enjoy some quiet time.The owner was very responsive and thoughtful, which made the whole experience even better. The beds were comfortable and we slept great each night.The location was also excellent. We were able to walk to nearby restaurants and easily stroll across the bridge into town, which made exploring the area very convenient. Overall, a great stay and we would happily come back.
This is our second time renting at this house, and it was as perfect as ever! Very clean, comfortable and a perfect location for all Annapolis has to offer.
Anne H.
Stayed 2 nights in Oct 2025
Response from VrboOwner on 27 Oct 2025
I love having you and your family!! Come back any time!!!
We had the best time and loved the house. The Host was very accomodating with answering questions and allowing us to check in early, and stay later than check out time. The hosue is the cutest, well stocked with everything you cokd think of needing. The beds were comfortable, shower was great and furniture comfortable. We were able to walk downtown with ony a short walk. There are restaurants within walking distance. We will definately recommend and book again if visiting the Annapolis area.
My family had a great time staying here during a lacrosse tournament. Host was the best and the house was great. My boys loved the pool and adults loved the proximity to the restaurants and bars. Will stay here again in future.
This was the perfect place for my high school friends weekend girls trip. The house's proximity to restaurants/bars and downtown was fantastic! Great use of space and the amenities were top notch. We had amazing chats while wading in the pool. Thanks for also for the great weather.
Jane Marie H.
Stayed 3 nights in Aug 2025
Response from VrboOwner on 7 Sept 2025
Hi!!
I ordered the perfect weather just for you ladies!!!! I'm glad you all took. Advantage of all the activities around the home! Come back ANY time!!
We really enjoyed our stay at this cozy cottage with an amazing backyard retreat. We had the pleasure of meeting our host Liz and she is super nice and extremely responsive. We are so happy we found this cottage and hope to have future visits.
Very nice, cozy property with a beautiful backyard. The kitchen was well stocked, and the host provided a welcome cheese and wine board. One item to improve the comfort of this home would be to get better couches for the living room and sunroom. Overall, we enjoyed our stay!
Rachel E.
Stayed 3 nights in Sep 2025
Response from VrboOwner on 3 Oct 2025
Rachel,
Sorry this isnt a 10! I know the weather did not Cooperate. It rained all 4 days and you choose to leave early. (I did offer a nights refund if I could book it on a 12 hour notice). A fluffy cozy couch would have been WONDERFUL!!
However, Staying with the cottage size I choose a custom upolstered, extra foam, thicker mattress, twin sleeper sofa to utilize the space. I also maximized the seating area by adding 4 chairs, 2 being swival. Again, trying to maxImize the unique space. Sorry a fluffy big cozy sofa would have been wonderful during a rainy stay. (I had a single large couch and it was to big, not much seating. I also had an apartment size couch but no sleeper. This arrangement has worked the best. But thank you for your input).
The sunroom sitting area is Also decorated to maximize and utilize thIs AMAZING space! Hanging out. Puzzels. Games. Coloring. Drying off from the pool before coming inside. Eating. Conversation. Watching TV. Sitting by the fireplace. Again, I added 2 swival chairs to maximize the usage of the unique space.
I hope you can come back and enjoy everything Annapolis and Eastport has to offer when it isn't raining for 4 days in a row and you can enjoy the outdoors a bit more. I'd love to have you again.
Liz
We loved our stay here! It was a lovely property, great location and the host was so thoughtful and left great welcome gifts for us!
Leslie P.
Stayed 2 nights in Mar 2024
Response from VrboOwner on 18 Mar 2024
I'm SO glad you all enjoyed a birthday weekend at 421 Irie!! A fun weekend of St Patty's Day celebrations and a birthday!!! I hope to see you all again.
Liz
We had a wonderful stay! Great house, very clean & comfortable, loved the pool & porch, and it was so nice to be able to walk to fun restaurants in Eastport and downtown Annapolis.
ashley S.
Stayed 4 nights in Jul 2021
Response from VrboOwner on 7 Dec 2021
Hi!!
I enjoyed having you!! It is totally located in the middle of everything!! Yet So FAR from everything if you choose!! Park the car in the drive way, take the keys and hide them until you're ready to check-out!! Easy Peasy!!!
I hope to see you again!
liz
Wonderful weekend stay for our multi-generation family visit. Everything was exactly as described and Liz was very easy to connect with. We did some light cooking and the kitchen was well-equipped with everything we needed. We loved all of the extra touches and conveniences. Easy access to Annapolis and lots of great food/drink options within easy walking distance. I wouldn't hesitate to book another stay.
Rebecca N.
Stayed 4 nights in Aug 2025
Response from VrboOwner on 3 Sept 2025
Hi, Wonderful guest!! (VRBO will no longer allow hosts to use first names :,(
I am glad you had a wonderful visit!!! Yes, the kitchen is totally LOADED, 😂😂!!
And there are like 10 such wonderful places with in 3 blocks to eat!!
I look forward to having you all again!!
Liz
About the host
Hosted by Liz
I am a care-free spirit! Hard working entrepreneur!! Who wants to share my experiences of the water, island fun, great food, and better company with my new friends! I had a short term vacation renal for 8 seasons in southern, MD. EXCELLENT 5 ⭐️ and was able to sell and purchase another great property and location in Annapolis. I hope you can enjoy some MD hospitality soon!!
Liz
Why they chose this property
This property has it all!! Location is key!! Annapolis is amazing!! Eastport, on the peninsula, is more laid back and less tourists!! Walk to be amongst the chaos, if you choose, or enjoy the local scene!! Compact with a big punch!!!! The feel of serenity in a wonderful town/village setting. Incredible flower gardens! Pool! Open floor concept. Entering at its best!!!! Just IRIE!!!
What makes this property unique
Off-street parking Full-size pool Fully fenced in back yard Location Self proclaimed Entertaining queen and avid gardener, is your hostess!!
Languages:
English
Premier Host
They consistently provide great experiences for their guests