Entire home

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

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

A modern two-story house with a brick pathway leading to the entrance, surrounded by a well-maintained garden with various flowers and shrubs. - 421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking! (Annapolis)
A spacious living room with a large TV, wicker furniture, and a view of the outdoors. - 421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking! (Annapolis)
A balcony with wicker furniture, a pool, and a view of surrounding buildings. - 421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking! (Annapolis)
A modern kitchen with wooden cabinets, a granite countertop, and pendant lighting. - 421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking! (Annapolis)
A modern kitchen with a large island, built-in oven, and a staircase with a railing. - 421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking! (Annapolis)
Close to Annapolis City Dock and U.S. Naval Academy, 421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking! provides a garden, a playground and laundry facilities. Stay connected with free in-room WiFi, with a speed of 500+ Mbps (good for 6+ people or 10+ devices), and guests can find other amenities such as babysitting service.

Reviews

10 out of 10
Exceptional

Popular amenities

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

Add dates for prices

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. :)

    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 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

Similar properties

About the area

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 John Smith House and William Paca 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 hiking and ecotours nearby. Visit our Annapolis travel guide
View more Holiday homes in Annapolis
Map
Annapolis, MD

What's nearby

  • A coastal town with a marina, houses, and a bridge in the distance.
    Spa Creek
    5 min walk - 0.4 km
  • A large building with ornate architecture, a cannon, and a sign reading "Bancroft Hall".
    U.S. Naval Academy
    17 min walk - 1.5 km
  • Annapolis Harbor
    2 min walk - 0.2 km
  • Annapolis Maritime Museum
    6 min walk - 0.6 km
  • Annapolis City Dock
    15 min walk - 1.3 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

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.

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 mile (2 km) of Annapolis Harbor, Annapolis City Dock and U.S. Naval Academy. Annapolis Maritime Museum and Spa Creek are also within 10 minutes.

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Reviews

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

10

Exceptional

10

Cleanliness

10

Location
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

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
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
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
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 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

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

Great Location

Nice house in a great location.
Stayed 3 nights in Jun 2024
Verified review

8/10 Good

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

Family visit

Great location.
Stayed 3 nights in Jan 2025
Verified review

10/10 Excellent

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

Perfect Perfect Perfect

great location and beautiful place to stay. We will be back if we are ever in the area again.
Stayed 3 nights in Nov 2023
Verified review

10/10 Excellent

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

10/10 Excellent

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

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!
Stayed 3 nights in Mar 2025
Verified review

10/10 Excellent

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

Perfect spot!

One of if not the best VRBO’s I’ve stayed in! Liz is the perfect host with so many added touches in her place. The location is perfect and the pool was a game changer for how hot it was! We will definitely be back!
Stayed 3 nights in Aug 2024
Verified review

10/10 Excellent

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

10/10 Excellent

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

Perfect spot for an Annapolis Weekend

We absolutely loved staying in this property. It’s comfortable, charming and so well appointed. It’s situated in a great location, within walking distance of all the special things Annapolis has to offer. The host was so easy to communicate with, and we really appreciate that she shares this beautiful home. We will’s definitely be back!
Stayed 2 nights in Nov 2024
Verified review

6/10 Okay

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

Convenient

Close to downtown Annapolis, restaurants
Stayed 3 nights in Sep 2024
Verified review

10/10 Excellent

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

Eastport escape

Fabulous house and pool in a great location. Owner was amazingly helpful and friendly. Wonderful week!
Stayed 7 nights in Jul 2023
Verified review

10/10 Excellent

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

Gem of a property 💎

We stayed at 421 Irie for a friend’s wedding. The property had everything we needed & then some! The kids loved the pool & you can’t beat the location!!!
Stayed 5 nights in Jun 2024
Verified review

10/10 Excellent

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

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.
Stayed 3 nights in Mar 2025
Verified review

10/10 Excellent

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

Usna tour.

This property is perfectly located. Toured usna and state house, many good restaurants nearby. Never had to use the car.
Stayed 4 nights in Jul 2024
Verified review

10/10 Excellent

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

Fun with good friends

absolutely fabulous home with gorgeous private garden with pool, Comfortable and beautiful interior with everything you could possibly need for your visit
Stayed 1 night in Aug 2024