Places to stay in Old Port, Portland

A cobblestone street is framed by historic red brick buildings. Umbrella-covered tables sit outside local shops and cafes. Green and blue storefronts add color, while potted plants enhance the walkways. A friendly atmosphere invites leisurely strolls through the charming neighborhood.

4.98 out of 5 average rating, 149 reviews

Modern Luxury with Bay Views * 5 Star Location!

Well-appointed, high-end private apartment with wide plank pine floors sourced from Western Maine, luxury bathroom and bedroom. Shared patio with grill and fire pit. A short walk to the Eastern Prom or restaurants of the Old Port and Washington Street. I pay attention to details such as cleanliness, local coffee, quality linens, furniture and furnishings. Queen bed with a view of the harbor. This is a non-smoking, non-cooking space. Not suitable for infants children. Hi speed internet.

4.98 out of 5 average rating, 313 reviews

Light-Filled Getaway with Private Porch

Spacious (1100 sqft), updated early Victorian (1838) apartment bordering the Arts District in Portland's historic and beautiful downtown West End. The apt. has great natural light, ample workspace, free on-street parking, a private garden entrance, and a sheltered, leafy screened porch. With a Walk Score of "95-A Walkers Paradise", you'll be able to stroll to nearby restaurants, cafes, museums, parks and Old Port. Then, return to a relaxing space that you'll be very happy to call 'home'!

A modern lounge area is highlighted by large skylights, allowing abundant natural light to fill the space. A sleek, white sectional is complemented by colorful accent pillows and a patterned area rug. Exposed brick walls add an element of rustic charm, with scenic views of the harbor visible through the glass.

4.97 out of 5 average rating, 270 reviews

Old Port Penthouse Suite - Amazing Harbor Views

2023 City of Portland Registration #20182242-ST Private Old Port Penthouse w/Breathtaking Views + Your Own Cupola. Quiet + Secure. Gorgeous contemporary suite full of light located right across from the working waterfront. Lobster and seafood off the boat is 100 meters from your front door. Watch the ferries to the islands from the cupola. Smell the salt air from your private deck. Welcome to Portland! Please note: animals (including assistance animals) not allowed due to owner's health.

A well-lit pathway runs alongside a wooden fence, bordered by plantings that enhance the outdoor space. The area is softly illuminated in the evening light, creating a welcoming ambiance for guests.

5 out of 5 average rating, 182 reviews

Private Garden Retreat on Munjoy Hill

This well-appointed, new space is located on first floor of a modern, new home on Munjoy Hill - Portland’s most charming neighborhood. This convenient suite has a separate, private entrance with a private outdoor seating area. The location is perfect for walking - just minutes to excellent restaurants, coffee shops, gourmet market, Eastern Promenade, St. Lawrence Arts Center and Washington Avenue. Portland’s Old Port and bustling harbor is just a 10 - 15 minute walk down the Hill.

Guest suite in Downtown Portland

A small bathroom features light green walls complemented by natural light from a mirror hanging above a white sink. A white towel hangs on a rack, and a small plant adds a touch of freshness. Adjacent, a white toilet and a cabinet contribute to a clean, minimalist look.

4.96 out of 5 average rating, 687 reviews

Studio, Walk to everything, Parking

5 to10 minute walk to all Portland has to offer; restaurants, breweries, galleries, shops, and famers markets. Located in a vibrant, safe, and transitional neighborhood. Steps from Portland's Arts district + Congress Street, (Portland Public Market, Broken Arrow, Regards, Portland School of Art). Home to Batson River Brewing & Distilling, ISA, Wilson BBQ. Short walk to downtown and the Old Port. Park your car and leave it for the duration of your stay. License # 20180110-ST

A clean and modern bathroom sink area features a white basin set into a speckled countertop. A black faucet and accessories, including a terracotta vase and amber-colored candle, are arranged near a round mirror. A graphic wall art piece complements the decor.

4.82 out of 5 average rating, 484 reviews

Walk-able Portland Studio

NEWLY RENOVATED! Cozy studio apartment in a historic building, located in Portland's East End Neighborhood. This location can't be beat! The Space features original hardwood floors, and large windows, subway tiled shower and thoughtful decor. Portland Food Co-Op is directly next door, as is the Walgreen's. Walking distance to Eventide, Honey Paw, Duck Fat, Hugos, Little Woodfords, LB Kitchen, Washington Ave Breweries and Distilleries and Old Port shopping district.

4.78 out of 5 average rating, 574 reviews

Apartment in West End

Downtown Studio, Walk Everywhere, Parking

The state of Maine requires all reservations must abide by current state travel restrictions. Please review before booking with us. You will love the location - just park at your reserved spot and forget about it! Great restaurants, bars, coffee shops, museums, Old Port, and Art Districts are all within 20 min walk. Fresh linens, towels, shampoo, french press, an insanely comfortable bed, and warm hospitality are provided, only bring your curious self!

4.92 out of 5 average rating, 282 reviews

A bathroom doorway opens into a compact space featuring a white toilet and a small sink. Light blue walls create a soothing contrast with the warm wood flooring. A mirror and a few shelves are mounted above the sink, providing functional storage.

Guest suite in East End

Gorgeous Studio 2 Blocks from Eastern Prom!

Located in Portland's trendy East End and within walking distance to the Old Port and Downtown, this beautiful studio is only 2 blocks from the Eastern Promenade and Casco Bay! You will have the Unit entirely to yourself with its own entrance, air conditioning, kitchenette, queen sized bed and an additional pull out single. Easily walk to all of the cool breweries, great restaurants, coffee shops, and night life! Welcome to Portland!

A small dining area is visible with a wooden table and two black chairs positioned near a window. Natural light enters through the window, complemented by light-colored window treatments. Two framed pictures adorn the gray walls, adding a touch of decoration to the space.

4.97 out of 5 average rating, 574 reviews

Cozy & Comfortable apartment in a perfect location

Bright sunny 1 bedroom private apartment in a quiet, Owner Occupied building. Perfect location. A short walk to Duckfat, Eventide and the rest of Portland. Top floor with full kitchen, work/desk area, comfortable living room, full bath with tub and shower, bedroom with a comfortable Queen bed. If you're a book lover, you'll enjoy it even more! Includes Reserved off street parking. Portland City License #STHR-000980

Condo in Downtown Portland

A welcoming living area is framed by sloped ceilings and large windows, allowing natural light to fill the space. Comfortable sofas are arranged around a coffee table, while decorative plants add a touch of greenery. A mirror reflects the inviting atmosphere.

4.92 out of 5 average rating, 167 reviews

Coastal Penthouse - Center of Downtown Portland!

Overlooking Portland’s historic downtown rests this coastal penthouse located on the most vibrant street in the city! This one-bedroom apartment is fitted out with all of the amenities needed for a Maine vacation! Enjoy relaxing in luxury while only feet away from Portland’s most popular destinations. This penthouse is perfect for those here for business or a Maine getaway!

Condo in Downtown Portland

A tree-lined street is seen, showcasing brick sidewalks and charming buildings of varied architecture. A black awning over a storefront adds contrast against the clear blue sky, while parked cars and outdoor seating hint at the vibrant atmosphere of the bustling downtown area.

5 out of 5 average rating, 142 reviews

Stylish Downtown Loft – Prime Location | A/C

This stylish 1-bedroom condo is perfectly situated in the heart of Portland's vibrant Old Port, right on iconic Exchange Street. Step outside and explore award-winning restaurants, breweries, gourmet coffee shops, and unique boutiques – everything Portland has to offer is right at your doorstep! License number: STHR-006583-2024 Check-in: 3PM, Check-out: 10AM

Condo in Downtown Portland

4.94 out of 5 average rating, 126 reviews

Modern Condo Portland's Historic Old Port District

Enjoy a stylish experience at this centrally-located loft. A converted factory building has been transformed into this chic and modern condo. Cobblestone streets, endless incredible dining and nightlife, boutiques, shops and historic architecture. A quintessential New England seacoast town and working waterfront.

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Popular amenities for Old Port, Portland places to stay

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Other great vacation rentals in Old Port, Portland

4.99 out of 5 average rating, 96 reviews

Chic Portland Penthouse, 2BR

JoeRating, 5 stars1 week ago

Amazing place in a fantastic walkable part of town. The host was super communicative and responsive, and the apartment was beautiful, clean, and had great amenities. We were in town with another couple and had an amazing time eating around town (highlights include Central Provisions and Duck Fat), went bowling at Bayside Bowl, went on a Narrow Gauge train tour, and caught a concert in Thompson’s Point. With the exception of the concert, everything was walking distance and frankly I don’t think the apartment could be in a better location.

The image shows the exterior of a historic brownstone in a city setting. Large glass doors provide entrance, flanked by a tall planter. The building's brick facade features a blend of dark and light tones, with a nearby shop window displaying floral arrangements and gifts.

5 out of 5 average rating, 51 reviews

Private Rooftop Deck/Artsy Apt/Old Port Arts Dist

ChalidaRating, 5 stars1 week ago

Dena was such a great host! The place was beautiful and in the perfect location. Just a short walk to so many awesome restaurants. The bed was really comfy, and the place actually looked even nicer in person than in the photos. We had a great stay and would definitely come back!

A bright bathroom is presented featuring a modern vanity with a circular sink, complemented by a wall-mounted mirror. A glass door shower is visible, surrounded by white walls. Two navy towels hang on polished chrome towel bars, while light streams in through a nearby window.

4.95 out of 5 average rating, 61 reviews

Charming Apartment- Munjoy Hill

RebeccaRating, 5 stars1 week ago

My partner and I loved this Airbnb! Inside was great and it was in a quiet and safe, but still walkable area. We appreciated the local recommendations - the hosts were very helpful!

A hallway leads into the apartment, featuring wooden flooring and textured walls. Light floods in from the living area at the end, revealing a dining table and chairs set against soft, neutral tones. A small rug adds warmth to the space, contributing to a welcoming atmosphere.

4.77 out of 5 average rating, 509 reviews

Downtown Apartment w/ Parking - Come Work or Play!

NicoleRating, 5 stars5 days ago

This place is truly a hidden gem to stay at location wise. Having the parking so close was a huge bonus to us and everything downtown is so walkable within .25-.5 mile from the location. Apartment was clean, couch was comfy, had everything you could need for a short term stay. The only negative would be that it seemed to be loud hearing noise from outside easily so we could hear a lot of people and cars nearby. If you’re sensitive to that, especially for sleeping that would be something to consider but it really didn’t bother us personally.

A spacious studio loft is illuminated by natural light, revealing exposed brick walls and wooden beams. A comfortable bed with striped bedding is positioned beside a modern television mounted on the wall. A cozy seating area includes a light-colored sofa, accompanied by a round coffee table and indoor plants.

4.96 out of 5 average rating, 660 reviews

Modern Studio Loft w/ Parking in Perfect Location

JudithRating, 5 stars1 week ago

We had a wonderful stay at Tom’s apartment. It is unquestionably a five-star rental. It is clean and comfortable with many amenities and the location is perfect with restaurants, venues and attractions only a 5-20 minute walk away. Check in, check out and parking instructions were very clear and easy to follow. Tom also provided a printed guide book with details for the apartment as well as suggestions for things to do and see in Portland which was very helpful and appreciated. We highly recommend and hope to be back soon to do some more exploring!

A historic brick building is adorned with climbing greenery, creating a natural aesthetic. The structure features multiple large windows, with light emanating from the upper floors. Tables are set outside, indicating an inviting dining atmosphere in a vibrant area.

5 out of 5 average rating, 21 reviews

Old Port Loft - 301

NancyRating, 5 stars1 week ago

The loft was just as it was pictured - even better! It was perfect for 2 couples with 2 king bedrooms and 2 baths. The water view from dining room was lovely - we spent hours playing games at the table and just enjoying the view and loft. Jennifer is an excellent host and responds quickly to any questions. I highly recommend #301!

A bright laundry room features several stacked white washing machines and dryers against a wall. A wooden table is centrally positioned in the room, surrounded by soft natural light coming from large windows with dark frames. The warm wooden flooring adds to the overall simplicity.

4.84 out of 5 average rating, 19 reviews

Old Port Studio prime location

VanceRating, 5 stars3 days ago

The unit is in a great location for exploring Portland. Everything we wanted to do was within walking distance. The unit was clean and suited our needs really well. The bed was very comfortable.

An antique marble mantle is illuminated from within, creating a warm glow. Above it, a decorative model sailboat rests, accompanied by a rectangular mirror reflecting the space. A cozy leather chair and a glass coffee table with magazines are positioned nearby against a rich green wall.