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421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

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A modern two-story house with a brick pathway leading to the entrance, surrounded by a well-maintained garden with various flowers and shrubs.
A spacious living room with a large TV, wicker furniture, and a view of the outdoors.
A balcony with wicker furniture, a pool, and a view of surrounding buildings.
A modern kitchen with wooden cabinets, a granite countertop, and pendant lighting.
A modern kitchen with a large island, built-in oven, and a staircase with a railing.

Reviews

10 out of 10
Exceptional

Entire home

2 bedrooms2 bathroomsSleeps 5102 sq m

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning

Explore the area

View map
Annapolis, MD
  • Place, Annapolis Maritime Museum
    ‪6 min walk‬
  • Place, Annapolis City Dock
    ‪15 min walk‬
  • Place, U.S. Naval Academy
    ‪17 min walk‬
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪40 min drive‬

Room options

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About the area

Annapolis

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. .Attractions within a 30-minute walk of this Eastport holiday home include Annapolis City Dock and U.S. Naval Academy.
View more Holiday homes in AnnapolisOpens in a new window

What's nearby

  • Annapolis Harbor - 2 min walk - 0.2 km
  • Spa Creek - 5 min walk - 0.4 km
  • Annapolis Maritime Museum - 6 min walk - 0.6 km
  • Annapolis City Dock - 15 min walk - 1.3 km
  • U.S. Naval Academy - 17 min walk - 1.5 km

Getting around

  • Odenton Station - 28 min drive
  • Baltimore Washington International Airport (BWI) - 45 min drive

Restaurants

  • ‪The Choptank - ‬15 min walk
  • ‪Royal Farms - ‬6 min walk
  • ‪Boatyard Bar & Grill - ‬3 min walk
  • ‪Iron Rooster - ‬17 min walk
  • ‪McGarvey's Saloon & Oyster Bar - ‬17 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 Licence 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. :)

CONTACT owner, Liz 301730100 for bookings

Owner:
Liz Hopkinson
3017301000
Emhopkinson@icould.com

Irie ~ to be at total peace with your current state of being.....
AKA NO WORRIES!!!!

This charming, 2 storey COTTAGE was Inspired by sun-drenched island holidays 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 colourful 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 City centre 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 mum and pop shops, several yacht clubs and marinas, museums, and of course.... WATER Activities!! You say, you're on holiday and just want to chillax, just stay in and simply enjoy your new holiday home!!

421 Irie has it all!!!!!

Start your day off with your morning drink from the built-in drink and breakfast nook. Savior your authentic French pastry from our local bakery, Bakers and Co., a short stroll away. Enjoy your sweet or savoury 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 city centre 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 choices 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 storey 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 alcoholic drink in the new (Apr. 2023) sunroom while listening to some island music, reading a book, marvelling 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 kerbside 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

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Property amenities

Beach

  • Beach loungers
  • Beach towels

Pool/Spa

  • Outdoor pool
  • Pool gate
  • Private pool

Internet

  • 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
  • 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

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

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

  • American Express
  • Discover
  • Mastercard
  • Visa

Important information

Optional extras

The fees and deposits listed below will be charged at the time of service, check-in, or check-out.

  • 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 has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
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 has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children. If you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room. 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 Bay Ridge Beach (3.4 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

Rating 10 - Excellent. 145 out of 151 reviews
Rating 8 - Good. 5 out of 151 reviews
Rating 6 - Okay. 1 out of 151 reviews
Rating 4 - Poor. 0 out of 151 reviews
Rating 2 - Terrible. 0 out of 151 reviews

10/10

Cleanliness

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location, clean, amazing pool, and responsive host.
Stayed 5 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Fabulous space for two couples. We took advantage of the pool and had a wonderful time. Convenient 10 min walk to great restaurants and shopping. Liz was a fabulous host.
Stayed 3 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location, charming decor, extra clean and well-provisioned.
Stayed 2 nights in Feb 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful experience! Liz is very communicative and ready to help in any way. The home is stocked with everything you could need and more! The location is excellent and so walkable! We would highly recommend Liz’s home to anyone! We look forward to returning in the future.
Stayed 3 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful and easy parking- charming and comfortable
Stayed 3 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great property and location.
Stayed 2 nights in Oct 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Liz is fantastic! The home is perfectly located to all the best spots, ease of walking over the bridge and adorable outdoor area in the back. Will definitely be back!
Stayed 3 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The home was very welcoming! The chosen decor was beautiful and the backyard was so pretty with the flowers and the other landscaping lent to a very relaxing atmosphere. The proximity of the house to several great restaurants was perfect and a short 15-20 min walk to downtown. A perfect girls weekend place!
Stayed 3 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a great stay! The house was adorable and the pool was awesome!
Stayed 2 nights in Jul 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had an excellent stay in this home, everything we could possibly need was provided.The home is in a great location to explore the area and within easy walking distance of the centre of Annapolis.Loved watching the wildlife in the garden and relaxing in the sun room - an oasis of calm after a day out.The house is very clean, well maintained and generously stocked.We rent VRBO houses regularly and this is one of the best!Liz is a great host, we are glad we selected this home and would happily return and recommend it to others.
Stayed 7 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Had a great stay. Kitchen was very well equipped. Beautiful home.
Stayed 4 nights in Nov 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Liz was the PERFECT host for our "Girlfriends' Birthday Staycation". Her home was the perfect location for us to relax and de-stress, re-charge with some vitamin D by the pool. Liz gave us great tips on avoiding traffic, activities and restaurants. Her home allowed us to leave her oasis with a feeling that "Everything is going to be alright"...IRIE!! We will definitely look forward to returning.THANK YOU LIZ!
Stayed 2 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 2 nights in Mar 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 2 nights in Oct 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great host! Great house!
Stayed 3 nights in Dec 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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
Stayed 2 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place

Wonderful house in a great location
Stayed 5 nights in Apr 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Cutest little cottage, just as described. Great location and a wonderful and thoughtful host.
Stayed 3 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Place is truly wonderful! And the host is even better! Wonderful time!
Stayed 3 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful stay!

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.
Stayed 4 nights in Jul 2021
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing host ! There to accommodate wherever you need!
Stayed 2 nights in Dec 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful property and great host!

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!
Stayed 2 nights in Mar 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This property is STUNNING!!! It is an amazing gem in Eastport and so walkable to restaurants and cute benches/waterfront seating. The home is well appointed and sunroom was FABULOUS to spend time in. We had our visit in spring but can see where the pool would be a main attraction in the summer months. We were out exploring most of the daylight but evenings were spent playing scrabble in the sunroom with family and enjoying our time together. So much to explore and IRIE 421 was the perfect home-base for my parents and I to enjoy the Annapolis area and history.
Stayed 4 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 3 nights in Sep 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 2 nights in Mar 2026