8 Coolest Hotels in Portland, Maine with Harbor Views, History, and Hipster Vibes

The Press Hotel used to house the offices and printing plant of the Portland Press Herald, the state’s largest newspaper. When I go to the Press Hotel for a Maker’s Mark Manhattan, I like to imagine myself as Clark Kent opening the tall, heavy doors on my way to balance my new hot tip for an article with saving the world. There are collections of typewriters and cases adorning the walls that invoke the mystical power of the written word. There are quotes all over the walls and a buzzing vibe in the bar area that feels like a writer’s pit.

The spacious rooms resemble old writer’s offices, but with the flair of mid-century style. They boast 110 rooms and suites with vintage-styled journalist desks, wood floors, local artwork, and woven wall tapestries by Portland-based artist Angela Adams.

Right downstairs is the fabulous Union Restaurant. Executive Chef and native son, Josh Berry, serves local food at its finest. Sip Maine wine with the three cheese appetizer that comes with blueberry crisps. Then, try out the Gulf of Maine sea scallops for a taste of how Portland does fresh seafood.

Just because you’re coming to a city doesn’t mean you can’t get some of that true Maine island experience. The Inn at Diamond Cove is so spectacular that locals make a regular pilgrimage once a year to its Diamond’s Edge Restaurant. Constructed during the 1890’s Fort McKinley’s was part of the country’s coastal defense system to protect Portland’s Harbor and Casco Bay. The Inn was Fort McKinley’s former Barracks. Cars are not permitted on the Island, only golf carts and bicycles allowed.

There are few Maine experiences as memorable as taking the ferry from Portland’s Old Port district through the sparkling waters of Casco Bay to peaceful Great Diamond Island. While the island is just a short boat trip away, it feels like a remote island retreat. The rooms and suites are enormous and filled with natural light. The salty air wakes you up and reminds you to appreciate the joy of nature.

Originally opened in 1927 as the Eastland Park Hotel, the Westin Portland Harborview Hotel has since been immaculately revived. It’s right around the corner from the State Theatre, a funky renovated theatre where hip local bands mix with touring indie artists.

Every guest room features a view of downtown, the harbor, or Casco Bay. Relax with a massage or facial at the Artné Spa before you head to the timelessly chic Top of the East rooftop restaurant with panoramic views. This penthouse bar is a portal into the past where women wore cocktail dresses and men jackets and ties.

This hotel is named after Francis Fassett, who designed the building as a home for Mellen E. Bolster in 1881. Born in Bath, Maine in 1823, Fassett was a leading architect for Maine in Portland and is credited with helping rebuild much of the city after the Great Fire of 1866. His influence continues on all over Portland by the designs of his most successful protégé and eventual partner, John Calvin Stevens. Creepily enough, in 1925, the Hay and Peabody Funeral Home purchased the Mellen E. Bolster House and opened their first funeral home on Portland’s peninsula.

But, in 2016, the property was bought with a hotel in mind. The Francis is a brick-front, 15-room hotel. The rooms are spacious and feature the elements one expects in a Victorian house, including private decks, reading nooks, and Victorian fireplaces. The neighborhood around The Francis has some true New England sensibilities — steadfastness and common sense. The row of houses where The Francis sits is more residential than many hotels, and its simple sign calls no attention to itself as any different from the rest of the buildings. It’s a luxurious way to find out what it feels like to live in Portland.

From a prohibition safehouse to Episcopal roots, from a boarding school to a bank, The Danforth has seen more than a handful of interesting characters since its 1823 construction. The first owner, Joseph Holt Ingraham, used his wife’s inheritance from a distant uncle to build this magnificent Federal-style mansion built on Danforth Street with the inheritance. The neighborhood was home to many wealthy merchants and The Danforth fits right in with the other mansions and stately homes in the area.

The mansion rooms are upscale and unique with built-in fireplaces. Waking up in Portland’s West End means going for long walks to brunch and a ferry ride to Peaks Island or a visit to a lobster boat with The Lucky Catch where you can learn all about the world of lobstering.

This hotel was built smack dab in the middle of the Old Port, right up the street from the waterfront. The rooms are nautically themed and luxurious. The service is accommodating with staff eagerly pointing out recommendations of their favorite things to do in Portland, like getting a snack at The Gelato Fiasco — specifically their creamy dark chocolate gelato.

The Portland Harbor Hotel ups their game by offering special deals throughout the year to make the most of local events. You can register for the Art Indulgence package, the Ice Bar, and the Bluefin Sunrise. In January, the hotel hosts magnificent outdoor ice bars serving specialty martinis from luges carved into the ice. Come anytime for the BlueFin Sunset where you’ll watch the sunset over the coastline as you eat fresh seafood.

Walking up the brick stairway to the tall pillars guarding the stately doorway of the Pomegranate Inn, one assumes a more austere stay is in store. It’s charming and citified. The classic exterior of this 1884 building disguises an interior filled with eclectic art and brightly painted walls. The inn feels like a laid-back gallery with almost every available surface covered by art. Large common spaces have bright faux-marble walls, a painted checkerboard floor, and a leopard-print runner. Walls of the rooms are hand-painted with fun florals, bird motifs, and even gold pom-pom balls, and no two rooms are alike.

The furniture is random, but not haphazard. Somehow it all comes together, creating a Seussian effect. You’ll leave wishing you could throw out all your furniture and start over. Just as the furniture reflects the differing tastes of the Inn’s owners, their buffet is diverse enough to satisfy any guest. For those who’d like a high-end experience, there are cucumbers filled with cream cheese, lox, and caviar. At the same time, there’s also good old fashioned oatmeal with toppings like brown sugar and walnuts.

Two blocks from Portland’s working waterfront stands the Portland Regency, constructed in 1895 as the Maine National Guard Armory. The detailed Neo-Gothic Romanesque building housed one of the finest and best-equipped armories in New England. The armory’s large drill hall served as a civic auditorium that held political events and holiday concerts. In 1942, the United States Navy took control of the structure and used it as a recreation center during World War II. De-commissioned in the 1950s, it became the city’s public bathhouse before being converted into a hotel in 1984.

Since 1984, the Regency has been a staple in Portland hospitality. The circular cobblestone driveway feels like a portal to 19th Century New England. The staff rushes out to grab your bags and usher you into the Portland Regency experience. Here among their 95 rooms and suites, you’ll see wing back chairs, gilt-framed oil paintings, and furnishings with classic colors like navy, burgundy, and khaki — trademarks the epitomize the quiet elegance of the New Englander.

Everything in the Old Port is accessible on foot. Stop into specialty shops like Folly 101 for tabletop accessories like vases and coffee table books. When you’re done shopping, head to a local brewery. Portlanders love their locally-produced brews. The seaside city was a pioneering force in the East Coast craft beer crusade and the brewing scene has only gained momentum. You’ll find tasting rooms at Rising Tide on Fox Street and at Lone Pine on Anderson Street where you can try their flagship Portland Pale Ale. (It smells like spruce with a strong citrus aftertaste. If you like bitter, this is your beer.)