This holiday home puts you in the heart of Annapolis, within just a 10-minute stroll of Annapolis Harbor and Annapolis Maritime Museum. Highlights at this holiday home include a kitchen, a private pool and a washing machine. .Home features free WiFi, free wired Internet and 2 bathrooms. In-room dining is easy with a kitchen that comes equipped with a fridge, a microwave and a stovetop. A pillowtop bed, premium bedding and a pillow menu invite a good night's rest. A fireplace, a patio and a sofa bed are also available. Housekeeping is available on request. .This smoke-free holiday home offers an outdoor pool and free WiFi in public areas, and has concierge services. Added amenities include laundry facilities, a garden and barbecues. Local cuisine breakfast is available daily between 8:00 AM and 11:00 AM. .Near this Eastport holiday home, you'll find U.S. Naval Academy.
Baltimore Washington International Airport (BWI) - 45 min drive
Restaurants
The Choptank - 15 min walk
Carrol's Creek Cafe - 4 min walk
Annapolis Market House - 16 min walk
O'Brien's Oyster Bar & Seafood Tavern - 17 min walk
Boatyard Bar & Grill - 3 min walk
About this property
Entire place
You'll have the entire home to yourself and will only share it with other guests in your party.
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!!
Available in the house: Free WiFi and wired internet
Parking and transport
Onsite parking includes off-street options
Kitchen
Blender
Coffee/tea maker
Cookware, dishware, and utensils
Dishwasher
Electric kettle
Hob
Ice maker
Microwave
Oven
Paper towels
Refrigerator
Spices
Toaster
Dining
Daily local cuisine breakfast available 8:00 AM to 11:00 AM for a fee: USD 12 to 18 per person
Chef service
Dining table
Bedrooms
2 bedrooms
Day bed
Down comforter
Egyptian cotton sheets
Hypo-allergenic bedding
Pillow menu
Pillowtop mattress
Twin sofa bed
Bathroom
2 bathrooms
Hair dryer
Shampoo
Shower
Soap
Toilet paper
Towels provided
Living spaces
Dining table
Fireplace
Living room
Entertainment
Books
Games
Smart TV with cable/satellite channels
Stereo
Outdoor areas
Barbecue grill
Fenced yard
Garden
Outdoor furniture
Patio
Picnic area
Laundry
Laundry facilities
Washing machine
Work spaces
Desk
Desk chair
Comfort
Air conditioning
Heating
Pets
No pets allowed
Suitability/Accessibility
No lift
Smoke-free property
Services and conveniences
Concierge services
Housekeeping on request
Iron/ironing board
Meal delivery service
Location highlights
In a historical district
In a village
In the city centre
Near a health/beauty spa
Near a hospital
Near an outlet shopping centre
Near the bay
Near the marina
On a river
Things to do
Bicycles
Boat
Birdwatching nearby
Casino nearby
Ecotours nearby
Fishing nearby
Free bicycles nearby
Golfing nearby
Health club (partner property) nearby
Hiking/biking trails nearby
Jet skiing nearby
Kayaking nearby
Motor boating nearby
Parasailing nearby
Sailing nearby
Swimming nearby
Water skiing nearby
Water tubing nearby
Wildlife walks nearby
Windsurfing nearby
Safety features
Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
Smoke detector (host has indicated there is a smoke detector on the property)
First aid kit
Fire extinguisher
Deadbolt lock
General
Bicycles
Garden
Housekeeping (on request)
Unit size: 1,100 square feet
Policies
Check-in
Check-in time starts at 3:00 PM
Contactless check-in and check-out are available
Minimum check-in age - 27
Check-out
Check-out before 11:30 AM
Contactless check-out
Special check-in instructions
The property charges 3 per cent for credit card payments
There is no front desk at this property
Guests can access their accommodation through a private entrance
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools
Check-out instructions
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.
Rules
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!!
Access methods
Access code, private entrance
Pets
No pets allowed
Children and extra beds
Children are welcome.
Rollaway/extra beds are not available.
Cots (infant beds) are not available.
Events
No events allowed
Smoking
Smoking is not permitted
Payment types
Important information
Optional extras
The fees and deposits listed below will be charged at the time of service, check-in, or check-out.
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
This may not be a comprehensive list. Fees and deposits are subject to change and might not include tax.
You need to know
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
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
This property is managed by a professional host. The provision of housing is linked to their trade, business or profession. This property accepts Visa, Mastercard, American Express, Discover, debit cards, mobile payments and PayPal. Cash is not accepted. On-site parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, a first aid kit and a deadbolt lock in all accommodation.
Property Registration Number 2280460
We should mention
The seasonal pool will open on 15 April and close on 25 October.
Frequently asked questions
Are there any beaches close to 421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!?
The closest beach to 421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking! is Sandy Point Beach (8.6 km).
Does 421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking! have a pool?
Yep, and guests love it! 421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking! has a pool. The pool is open from April 15 to October 25.
What luxury perks are available at 421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!?
This property features an outdoor pool, as well as a private pool and pillowtop beds.
Is 421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking! family-friendly?
You bet! With amenities such as a playground and laundry facilities, as well as children's dinnerware and children's books, it's no surprise that 421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking! is a winner with our family travellers.
Is there a private hot tub at 421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!?
No, but there is a private pool.
Does 421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking! serve breakfast?
You bet, local cuisine brekkie is available daily between 8:00 AM and 11:00 AM.
Is there a free airport shuttle available at 421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!?
No, 421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking! does not offer an airport shuttle service.
What time are check-in & check-out at 421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!?
Check-in begins at 3:00 PM. Check-out time is 11:30 AM.
Are pets allowed at 421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!?
No, pets are not allowed.
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking! Reviews
Reviews
10
Exceptional
All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
Rating 10 - Excellent. 124 out of 129 reviews
10 - Excellent
124
Rating 8 - Good. 4 out of 129 reviews
8 - Good
4
Rating 6 - Okay. 1 out of 129 reviews
6 - Okay
1
Rating 4 - Poor. 0 out of 129 reviews
4 - Poor
0
Rating 2 - Terrible. 0 out of 129 reviews
2 - Terrible
0
10/10
Cleanliness
Reviews
10/10 Excellent
Carla M.
2 Jan 2026
Liked: Cleanliness
Great host! Great house!
Carla M.
Stayed 3 nights in Dec 2025
10/10 Excellent
Elizabeth E.
17 Dec 2025
Liked: Cleanliness
Amazing host ! There to accommodate wherever you need!
Elizabeth E.
Stayed 2 nights in Dec 2025
10/10 Excellent
sandy d.
15 Dec 2025
Liked: Cleanliness
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.
sandy d.
Stayed 2 nights in Nov 2025
10/10 Excellent
Larry P.
3 Dec 2025
Liked: Cleanliness
Had a great stay. Kitchen was very well equipped. Beautiful home.
Larry P.
Stayed 4 nights in Nov 2025
10/10 Excellent
DIXIE M.
5 Nov 2025
Liked: Cleanliness
DIXIE M.
Stayed 5 nights in Oct 2025
10/10 Excellent
Anne H.
26 Oct 2025
Liked: Cleanliness
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
10/10 Excellent
Steve N.
22 Oct 2025
Liked: Cleanliness
Great property and location.
Steve N.
Stayed 2 nights in Oct 2025
8/10 Good
Rachel E.
28 Sept 2025
Liked: Cleanliness
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
10/10 Excellent
Sharon A.
22 Sept 2025
Liked: Cleanliness
This was the perfect place for the three of us. While we could easily walk (or ride the bikes!) All over Eastport and downtown, it was really nice to also have a place to park the rental car. I would highly recommend this super cute, well-appointed little cottge. Liz was so communicative, offering us early check in and late check out. Gorgeous decor and beautiful gardens.
Sharon A.
Stayed 3 nights in Sep 2025
10/10 Excellent
Randy S.
15 Sept 2025
Liked: Cleanliness
Randy S.
Stayed 7 nights in Aug 2025
10/10 Excellent
Angelica J.
8 Sept 2025
Liked: Cleanliness
Great property! We loved our stay. Liz was fantastic and easy to reach if needed. It was close to USNA and easy to either UBER or walk.
Angelica J.
Stayed 3 nights in Sep 2025
10/10 Excellent
Jane Marie H.
7 Sept 2025
Liked: Cleanliness
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
10/10 Excellent
Gregory P., Northern New York
5 Sept 2025
Liked: Cleanliness
Place is truly wonderful! And the host is even better! Wonderful time!
Gregory P.
Stayed 3 nights in Aug 2025
10/10 Excellent
Rebecca N.
21 Aug 2025
Liked: Cleanliness
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
10/10 Excellent
Nancy D.
15 Aug 2025
Nancy D.
Stayed 3 nights in Jul 2025
10/10 Excellent
Nicole W.
8 Aug 2025
Liked: Cleanliness
Cutest little cottage, just as described. Great location and a wonderful and thoughtful host.
Nicole W.
Stayed 3 nights in Aug 2025
10/10 Excellent
Kathleen J.
1 Aug 2025
Liked: Cleanliness
We had a great stay! The house was adorable and the pool was awesome!
Kathleen J.
Stayed 2 nights in Jul 2025
10/10 Excellent
Petra L.
13 Jul 2025
Liked: Cleanliness
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.
Petra L.
Stayed 3 nights in Jul 2025
10/10 Excellent
Tim L.
3 Jul 2025
Liked: Cleanliness
Great location
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.
Tim L.
Stayed 3 nights in Jun 2025
10/10 Excellent
Laura B.
30 Jun 2025
Liked: Cleanliness
Convenient oasis
We thoroughly enjoyed our stay at this home! From check in to check out, everything was a dream. The location has tons of cute restaurants (Adam’s on 4th was a favorite) and is super convenient. We visited during a heatwave and the pool was invaluable. The owner, Liz,has obviously worked very hard to make this place feel like a home away from home. Highly recommend!
Laura B.
Stayed 4 nights in Jun 2025
10/10 Excellent
Matthew T.
30 Jun 2025
Liked: Cleanliness
Perfect pool for family/kids
Early summer stay and the house, especially the pool, was very clean and tidy. Relaxing and secluded outdoor area with a larger than expected pool for the kids to enjoy. About 0.5 miles to the center of town with excellent restaurants less than 0.25 miles away in Eastport.
Matthew T.
Stayed 3 nights in Jun 2025
10/10 Excellent
Watersyrene, Homosassa, FL
31 May 2025
Liked: Cleanliness
Perfection
Wonderful experience - host is gracious and extremely accommodating. House is gorgeous- beds were clouds to dream on. Location is amazing. Should never head back to Annapolis- this is my place. Off street parking was a serious perk. Book this before someone else does- you won’t regret it!
Watersyrene
Stayed 2 nights in May 2025
10/10 Excellent
Carla M.
19 Apr 2025
Liked: Cleanliness
Great place
Wonderful house in a great location
Carla M.
Stayed 5 nights in Apr 2025
10/10 Excellent
John O.
22 Mar 2025
Liked: Cleanliness
Annapolis trip to visit family
Beautifully decorated small house. Very well equipped; complimentary beverage, cheeses and charcuterie tray were a pleasant surprise. Despite being only barely into spring there were lots of flowers blooming in the backyard garden.
John O.
Stayed 3 nights in Mar 2025
10/10 Excellent
Emily M.
17 Mar 2025
Liked: Cleanliness
Fantastic house!
My friends and I were looking for a relaxing place to have a long weekend - this place was great! The location was wonderful and the house had everything we needed. The host was a fabulous communicator and helped us with everything we needed! Can’t wait to stay here again!