Downtown Portland stay.A stay at this Downtown Portland condo places you steps from Fore Street Gallery and within a 5-minute walk of Casco Bay. Casco Bay Lines Ferry Terminal and Merrill Auditorium are also within half a mile (1 km).
Casco Bay Lines Ferry Terminal - 3 min walk - 0.2 miles
Merrill Auditorium - 8 min walk - 0.5 miles
Cross Insurance Arena - 8 min walk - 0.5 miles
Portland Museum of Art - 13 min walk - 0.7 miles
State Theatre - 15 min walk - 0.8 miles
Getting around
Portland Transportation Center - 9 min drive
Portland Intl. Jetport Airport (PWM) - 18 min drive
Restaurants
DiMillo's On the Water - 3 min walk
The Porthole - 2 min walk
Gilbert's Chowder House - 2 min walk
Harbor Fish Market - 2 min walk
Portland Lobster Company - 2 min walk
About this property
Entire place
You'll have the entire apartment to yourself and will only share it with other guests in your party.
Penthouse Two Master Waterfront Suite with Rooftop
2023 City of Portland Registration #20185280-ST
Stunning penthouse suite with exposed beams, brick accents, and whitewashed poplar walls. Enjoy harbor views from the rooftop deck. Two private master suites feature custom tile showers, one with a soaking tub. The spacious kitchen offers granite countertops and modern appliances. Relax by the gas-fired stove in the inviting living room. In-unit washer/dryer and elevator access included. Please note: no animals permitted due to owner's health.
Completely renovated guest suites within a charming 1850s warehouse on Portland's historic working waterfront, offering stunning views of the renowned Dimillo's Marina. Watch yachts glide by or enjoy dinner at a number of award winning restaurants within walking distance.
The spacious, modern kitchen is outfitted with sleek white shaker cabinets, stainless steel appliances, a wine cooler, cookware, glassware, cutting board, and a 12-cup coffee maker, complemented by a granite-topped island and bar stools. An open-concept dining area flows seamlessly into the living space, creating an inviting atmosphere.
Exposed brick walls and vaulted ceilings with skylights add an abundance of character to the guest suites.
Amenities include Wi-Fi, RokuTV, built-in speakers with a stereo system, ample closet and pantry space, linens, bedding, towels, hair dryer, shower essentials, and an iron and board.
Enjoy a private deck from your living room and semi-private rooftop deck, while floor-to-ceiling windows in the living room provide panoramic views of the waterfront at every hour.
The entire two-bedroom, two-and-a-half-bath unit is yours to enjoy during your Portland stay. The rooftop, shared with just one other unit, features a private seating area reserved exclusively for you, ensuring a peaceful retreat.
I am available throughout your entire stay to answer any questions you have. I typically respond within 30 minutes or less.
Located in the heart of the Old Port on the working waterfront, this is Portland, Maine at its core. See a mix of lobster boats and fisherman as well as busy professionals.
Must see spots nearby: *Harbor Fish: the go-to spot for just-caught fish *Casco Bay Ferry: visit the islands *J's Oyster: classic cocktails, seafood, and an unbeatable mix of locals and tourists alike *The Holy Donut: Maine potato donuts *Exchange Street: shopping *Novare Res Bier Bar: large selection of craft brews
Whole Foods, Trader Joe's, and Hannaford within a 1 mile drive.
We provide you with one monthly parking pass that allows 24/7 vehicle storage for one car. This same lot offers 24/7 parking for a second vehicle (on your own) for roughly $40/day or an adjacent lot offers 24/7 parking for a second vehicle for $15/day.
If traveling with more than 4 people, please inquire about our sister suite on the same floor. HOUSE RULES:
Below please find the House Rules. We want you to have an enjoyable stay with us and appreciate your adherence to the Rules. Any violation of the House Rules may result in forfeiture of your Security Deposit.
CHECK IN / CHECK OUT TIMES: Check in time is any time after 4:00 PM. Check out time is 11:00 AM. We ask that you kindly respect check out time as cleaning staff will arrive to clean the apartment for our next guests.
NUMBER OF GUESTS: The maximum occupancy for this apartment is 4 and may not be exceeded without specific permission from the owner.
MINIMUM AGE TO BOOK: 30
NO PETS: There are no pets of any kind allowed in the apartment.
NO SMOKING: There is no smoking of any kind allowed in the apartment. This includes, but is not limited to, cigarettes, e-cigarettes, cigars, pipes, and vape devices. You may not smoke in the apartment, on the private deck, nor anywhere in the entire building. If you wish to smoke, you need to take the elevator to the ground floor and smoke outside of the building. Evidence of smoking will result in loss of your security deposit.
CONDUCT: You are expected to behave reasonably and responsibly during your stay. Any unreasonable conduct in the apartment, on the balcony or in the building may be grounds for expulsion and the loss of your security deposit. Unreasonable conduct includes but is not limited to: indecent, rude or obnoxious behavior; dangerous or intentionally destructive acts; holding a party without the owner’s explicit permission; playing loud music; excessive drinking; the abuse of legal drugs or any use of illegal drugs; or otherwise acting in an inappropriate manner. Any damages or injuries to yourself, others, the apartment, or the building while engaging in unreasonable conduct is not the responsibility of the owner or his insurance company.
PLEASE NOTE: There are occupied office spaces directly beneath this unit. Accordingly, please keep noise to a minimum during weekday work hours. Parents, this includes noise from children, including but not limited to running in the unit.
FURNISHINGS: The apartment is fully equipped with bedding and bath towels, cooking pots and utensils, dishware and starter paper products for your use during your stay. Depending on the length of your stay, you may need to replenish paper products and soaps.
TOWELS AND LINENS: Please be respectful of linens and towels. Makeup/foundation and tanning products will stain. We have provided you with makeup wipes and black "makeup" towels for your use.
INCURRED EXPENSES: Any expenses incurred by the owner during your stay that are over and above what the owner agreed to in your rental agreement will be deducted from your security deposit. Any such expenses beyond your security deposit are still your responsibility and will be invoiced to you. The owner will inspect the property and pay any related invoices for services related to damage, and monies owed will be collected from you by whatever payment method you initially used.
CLEANING: The apartment is meticulously cleaned in preparation for your visit, and you are asked to leave the residence clean and in good order. You are required to clear the refrigerator, run the dishwasher, gather your trash. Please do not remove duvet covers from comforters.
WEATHER / NOISE: The owner is not responsible for the weather or other acts of nature and cannot guarantee peaceful and quiet enjoyment in the urban waterfront environment in which this apartment is located. Noises generated by construction, people, traffic, maritime activities, pets or wildlife outside the apartment are not an occurrence that warrants a refund of any kind.
THANK YOU!
We hope you have a wonderful time during your visit here. Please make lots of great memories and don’t hesitate to contact us if we can help make your stay more comfortable.
Scott & Karen
Important Note: Our cancellation policy as outlined on the booking website is firm. Please read it carefully. No refunds or exchanges will be given for travel issues on your end, including but not limited to flight delays/cancellations, vehicle issues, health problems/illness, family emergencies, weather, late arrivals/early departures, or any other unexpected issues that prevent cancellation after the given date range. We are holding your reservation for you and will not be able to rent it after a certain date. Therefore, we highly recommend that you purchase travel insurance to cover any unexpected events.
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
General
Unit size: 1,600 square feet
Policies
Check-in
Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 30
Check-out
Check-out before 11:00 AM
Special check-in instructions
You will receive an email from the host with check-in and check-out instructions
Pets
No pets allowed
Children and extra beds
Children are welcome.
Events
No events allowed
Smoking
Smoking is not permitted
Important information
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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm 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 private host, not a professional engaged in trade or business. This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, and a first aid kit in each accommodation.
Property is also known as
Henry Penthouse Suite Amazing Views Waterfront Heart Condo
Henry Penthouse Suite Amazing Views Waterfront Heart Old Port
Henry Penthouse Suite Amazing Views Waterfront Heart
Henry Penthouse Suite Amazing Views Waterfront Heart Condo
Henry Penthouse Suite Amazing Views Waterfront Heart Old Port
Henry Penthouse Suite Amazing Views Waterfront Heart Condo
Henry Penthouse Suite Amazing Views Waterfront Heart Old Port
391393
Henry Penthouse Suite Amazing Views Waterfront Heart
Frequently asked questions
How close is Penthouse Two Master Waterfront Suite with Rooftop to the airport?
This condo is 5.1 mi (18-min drive) away from the Portland Intl. Jetport Airport (PWM) airport, the closest popular airport to the property.
Does Penthouse Two Master Waterfront Suite with Rooftop have an airport shuttle?
Airport shuttle services are not available at this condo.
How close is Penthouse Two Master Waterfront Suite with Rooftop to the beach?
This condo is 15.3 mi (31-min drive) from Old Orchard Beach and 1.1 mi (2-min drive) from East End Beach. Don't forget your sunscreen!
Does Penthouse Two Master Waterfront Suite with Rooftop offer free breakfast?
This condo does not offer free breakfast.
Is there a casino at Penthouse Two Master Waterfront Suite with Rooftop?
No, there is no casino at this condo.
What time is check-in at Penthouse Two Master Waterfront Suite with Rooftop?
Check-in begins at 4:00 PM.
Is there free parking at Penthouse Two Master Waterfront Suite with Rooftop?
Free parking is not available at this condo.
Does Penthouse Two Master Waterfront Suite with Rooftop have a pool?
This condo does not have a pool.
Does Penthouse Two Master Waterfront Suite with Rooftop have a spa?
There are no spa services available at this condo.
How close is Penthouse Two Master Waterfront Suite with Rooftop to downtown Portland?
This condo is 0.4 mi away from Portland.
Reviews
Penthouse Two Master Waterfront Suite with Rooftop Reviews
10
Exceptional
All reviews shown are from real guest experiences. Only travelers 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.
10/10
Cleanliness
Rating 10 - Excellent. 245 out of 251 reviews
10 - Excellent
245
Rating 8 - Good. 6 out of 251 reviews
8 - Good
6
Rating 6 - Okay. 0 out of 251 reviews
6 - Okay
0
Rating 4 - Poor. 0 out of 251 reviews
4 - Poor
0
Rating 2 - Terrible. 0 out of 251 reviews
2 - Terrible
0
Reviews
10/10 Excellent
Sean B.
Sep 8, 2025
Liked: Cleanliness
Loved the location and proximity to everything. Looking forward to revisiting.
Sean B.
Stayed 7 nights in Sep 2025
10/10 Excellent
Mark L.
Aug 16, 2025
Liked: Cleanliness
Modern, bright, and clean. Gorgeous views.
Mark L.
Stayed 5 nights in Aug 2025
10/10 Excellent
Pat & Bill H.
Aug 3, 2025
Liked: Cleanliness
Amazing location. Looks just like the listing. Everything is pristine. And the parking space is such a convenience! Would love to return
Pat & Bill H.
Stayed 5 nights in Jul 2025
10/10 Excellent
Tina C.
Jul 16, 2025
Liked: Cleanliness
One of our favorite places that we have stayed! Will definitely be back!
Tina C.
Stayed 3 nights in Jul 2025
10/10 Excellent
Deanne B.
Jul 16, 2025
Liked: Cleanliness
fabulous stay
The location and views are spectacular. We love these condos and it is such a treat to stay in them.
Deanne B.
Stayed 8 nights in Jul 2025
10/10 Excellent
Amy M.
Jul 1, 2025
Liked: Cleanliness
Traveled with our 18 and 20 year old daughters
Perfect location! Fabulous condo!
Amy M.
Stayed 4 nights in Jun 2025
10/10 Excellent
Frank F., Norfolk
May 30, 2025
Liked: Cleanliness
Maritime
We stay here twice a year, in the spring and fall. Highlights are the farmers market, fish market, restaurants and hiking. We also love to just sit in the living room and watch the boats.
Frank F.
Stayed 3 nights in May 2025
10/10 Excellent
david l.
May 26, 2025
Liked: Cleanliness
Wedding weekend in Portland
We were in town for a wedding weekend (2 couples). The Henry suite was outstanding. Great lication and accommodations. Easy access to all points of interest and the hosts were great! I would recommend this to all my friends and relatives!
david l.
Stayed 3 nights in May 2025
10/10 Excellent
jeanette b., Dallas
May 21, 2025
Liked: Cleanliness
Would Stay Again
Excellent lodging and location, Would absolutely stay again.
jeanette b.
Stayed 3 nights in May 2025
8/10 Good
Leon J.
Apr 27, 2025
Liked: Cleanliness
Keep Coming Back
Have stayed at this location at least 6 times. Feel very comfortable here. View of the harbor is wonderful. Availability for parking is essential. Great kitchen and appliances. Washer/dryer is great. Response from owner is immediate. The problems we had this time have happened every time we have stayed. The tv connection is impossible to correct. Even when assistance was provided by the wonderful technician working for the owner, the tv's still are inconsistent from day to day, losing signals, and can't find major tv networks. Also, this time I couldn't use my laptop as them internet connection could not be made. Gave up trying. When I went to other outside locations in Portland, my laptop worked fine. These two issues, while possibly related, need looking into. We keep coming back for all the good things about it, but the items I have mentioned make our stay incomplete.
Leon J.
Stayed 4 nights in Apr 2025
10/10 Excellent
Jack L.
Apr 8, 2025
Liked: Cleanliness
Perfect Location!
We absolutely loved staying here. It is a modern, beautiful, centrally located place. The windows are fantastic-the showers were amazing. Walking to and from shops and local eateries was easy. The parking was beyond easy! We highly suggest this location!
Jack L.
Stayed 2 nights in Mar 2025
10/10 Excellent
Catherine P.
Apr 1, 2025
Liked: Cleanliness
Family and friends fun
Enjoyed our 2nd stay..great location
Catherine P.
Stayed 3 nights in Mar 2025
10/10 Excellent
Susan S.
Mar 13, 2025
Liked: Cleanliness
Portland waterfront
We can’t say enough how pleased we were with this location, perfect for walking to the restaurants and the Eastern Promenade trails. We enjoyed the evening sounds of boats and gulls. Check in was very easy and well written instructions for departure.
Susan S.
Stayed 4 nights in Mar 2025
10/10 Excellent
Jarrett W.
Mar 3, 2025
Liked: Cleanliness
Beautiful Condo Amazing Location
This property was wonderful and met all of our needs. The home is very clean and had everything needed for our stay. The location and views were amazing!!! Highly recommended and we'll definitely be staying here again. Thank you!!
Jarrett W.
Stayed 3 nights in Feb 2025
10/10 Excellent
Cheryl F.
Mar 3, 2025
Liked: Cleanliness
Friends winter vacation!
The Henry penthouse was such a great place. Location and views were amazing! From the minute we arrived everything was smooth and described perfectly. Wish we would have booked more nights, we will definitely be back! Thank you Scott & Liz
Cheryl F.
Stayed 3 nights in Feb 2025
10/10 Excellent
Mallory S.
Feb 17, 2025
Liked: Cleanliness
Worth every penny!
Booked this for a winter getaway and my husband and I were impressed from the start. Not only was the communication crystal clear with the hosts, the property was immaculate. The apartment itself was well furnished, and the view is stellar. We took full advantage of the kitchen, and didn’t lack for a thing— including an oyster shucker. The cherry on top was the parking, which was such a great amenity and convenience.
Mallory S.
Stayed 4 nights in Feb 2025
10/10 Excellent
Kathleen G., Asheville
Jan 27, 2025
Liked: Cleanliness
A Memorable Stay at Henry's Penthouse in Portland
We had a fantastic stay, and it was a great pleasure to make this charming place our home while visiting our newborn granddaughter, daughter-in-law, and son. The penthouse apartment is beautiful and has everything you could wish for. The bathroom and bedroom were terrific, and the cooking appliances and equipment made settling in a breeze.Moreover, the apartment's location is a traveler's dream, allowing for convenient foot exploration of downtown Portland. The neighborhood is safe, the view is breathtaking, and the parking is designed for easy access to the unit.The check-in process was a breeze, with easy access points from the back and front doors. The apartment is surrounded by various amenities, including shopping outlets, bars, and restaurants, all within a short walk. Our personal favorites, Harbor Fish and Jay's Oysters were just a few steps away.We are immensely grateful to the owners for their warm hospitality and for making our stay memorable. We wholeheartedly recommend Henry's Penthouse to anyone looking for a comfortable and enjoyable stay in Portland.
Kathleen G.
Stayed 5 nights in Jan 2025
10/10 Excellent
Megan R.
Jan 20, 2025
Liked: Cleanliness
Gorgeous view, cosy comfort
We loved our stay. The apt is equipped with everything you need and so cozy with the fireplace and sun streaming in the windows.
Megan R.
Stayed 3 nights in Jan 2025
10/10 Excellent
Ryan M.
Jan 15, 2025
Liked: Cleanliness
Everything you need & more - plus the VIEW !
Location is first and foremost the best part, close to everything in the heart of Old Port. Views are incredible and has every amenity you could ask for. Property managers communication was a amazing and the building is super secure with multiple coded entries. Will stay again for our next trip back!
Ryan M.
Stayed 3 nights in Jan 2025
10/10 Excellent
Nick
Jan 3, 2025
Liked: Cleanliness
Old Port
Great property in the heart of the Old Port.
Nick
Stayed 3 nights in Dec 2024
10/10 Excellent
Michaela S., Cambridge, MA
Jan 2, 2025
Liked: Cleanliness
Henry Penthouse
Great location and wonderful harbor views! Walkable to restaurants, shops, and nearby Harbor Fish Market. Kitchen was well equipped. Communication with host was easy.
Michaela S.
Stayed 2 nights in Dec 2024
10/10 Excellent
Verified traveler
Dec 23, 2024
Liked: Cleanliness
This is the 1
If you’re debating where to stay in the Old Port, this is the place. Lovely unit with an amazing view and excellent location. It is even better than in the photos.
Verified traveler
Stayed 4 nights in Dec 2024
8/10 Good
Rebeccah S.
Dec 13, 2024
Liked: Cleanliness
Another Gorgeous Portland Weekend
This is our fourth visit to one of Scott & Karen’s Portland penthouse properties—and as always, it was excellent. The apartment is in a fantastic area to explore everything Portland has to offer, and offers a lovely respite to return to after a busy day. This was the first year we had a little hiccup—the internet wasn’t working properly our first night, and required several calls to Scott’s property manager, as well as the cable company to get things sorted out. I was able to connect with Scott after the trip and give my feedback about the cable issues and slow communication from property management.
Rebeccah S.
Stayed 2 nights in Dec 2024
10/10 Excellent
Mindy B.
Dec 3, 2024
Liked: Cleanliness
Great stay
Great property with an amazing view and location.
Mindy B.
Stayed 7 nights in Nov 2024
10/10 Excellent
Carolyn S.
Nov 11, 2024
Liked: Cleanliness
Perfect
Excellent location, amenities, views... no detail was overlooked by the hosts. We had a lovely time.