Top 10 Cool and Unusual Hotels in Portland, Maine 2023

Revered for its quaint and gorgeous preservation of the past and for once voted the #1 Coziest City in America, Portland (the original Maine version) is becoming increasingly more popular with out-of-state visitors. It’s filled with beautiful architecture in the form of Victorian-era homes, chic boutiques, interesting museums, converted warehouses turned into award-winning restaurants, and a rich maritime history – so expect picturesque lighthouses and coastal forts.

From quirky chic boutiques to modern design high rises, here are some of the best cool and unusual hotels in Portland, Maine (in no particular order, they’re all awesome)

1. Blind Tiger Guest House – a unique historic boutique-style 19th-century inn that offers luxurious rooms 

Blind Tiger Guest House - Portland, Maine Blind Tiger Guest House - Portland, Maine1

For that special occasion, insist on a stay at the Blind Tiger Guest House. It is an elegant, 1820s Federal-style mansion that has been stylishly updated to offer guests gracious amenities like a billiard room, a conservatory, an enclosed garden and sun terrace, and a sitting room for convivial conversation.

Located close to the historic Old Port, from the hotel you can quickly access trendy local dining establishments and diverse recreational and cultural opportunities.

The luxurious rooms and suites are immaculately finished in a stylish 19th-century décor with modernized features. Many of the rooms even have wood-burning fireplaces, and a light breakfast is available from “The Pantry”.

2. Canopy By Hilton Portland Waterfront – a hip, trendy and very Instagrammable hotel perfect for partying Millennials and Gen Zs

Canopy By Hilton Portland Waterfront Canopy By Hilton Portland Waterfront1

For a hotel with a difference, you could treat yourself to a stay at the Canopy By Hilton Portland Waterfront. This refined accommodation is located in the Waterfront Historic District which is ideal for sightseeing or spending some time down at Casco Bay just a ten-minute walk away.

What makes this downtown property so distinctive is Luna, the fabulous rooftop bar with outdoor seating. It is the perfect way to wind down from your day of immersing yourself in all the nearby attractions.

Watch the sunset while sipping a cocktail and enjoy the breath-taking panoramic views over downtown Portland and out across the bay.

3. The Press Hotel, Autograph Collection – a chic and trendy hotel where guests can appreciate amazing city views

The Press Hotel, Autograph Collection - Portland, Maine The Press Hotel, Autograph Collection - Portland, Maine1

This grand hotel with spectacular city views, inhabiting a classic heritage brick building in the heart of the Old Port district, claims a unique style all of its own. It has a newspaper theme with an awe-inspiring ‘letterpress art wall’ dominating the front desk.

This breath-taking two-story high work, called the SWARM, features vintage typewriters and newsroom paraphernalia depicting the bygone chaos of old newspaper offices.

The upscale rooms and suites have the same newspaper chic styling, inspired by a press editor’s office from the 1920s and 1930s complete with a vintage journo’s desk and fun newsroom themes prominent everywhere in the décor. The hotel has a fabulous art gallery featuring the work of local artists.

4. The Francis – a locally owned boutique hotel that offers a friendly and personal service 

The Francis - Portland, Maine The Francis - Portland, Maine1

At the Francis Hotel & Spa, you will be welcomed by a grand, red-brick building with an elaborate, heritage-style portico gracing the entry.

This charming 19th-century mansion is situated in the upscale Parkside neighborhood in Portland’s West End Arts district, close to the Portland Museum of Art and not far from Deering Oaks Park.

For a relaxing stay in this one-of-a-kind Victorian-style boutique hotel, enjoy the in-house spa and wellness center, or dine at their farm-to-table restaurant before chilling out in one of the tastefully appointed lounges.

The hotel is a strong contributor to the community, with commitments like collaboration with the ‘Indigo Arts Alliance’, sponsoring the ‘Mayo Street Arts’ organization, and being a partner of the ‘Full Plates Full Potential’ campaigns, like ‘Feed Kids’.

  • To book, check prices or availability for The Francis

5. Portland Harbor Hotel – an elegant boutique-style place to stay, ideal for a romantic break

Portland Harbor Hotel - Portland, Maine Portland Harbor Hotel - Portland, Maine1

For something special, treat yourselves to a stay at the boutique Portland Harbor Hotel in downtown Portland. This sophisticated property is Old Port’s only Triple A-rated 4 diamond hotel.

Book a guest suite offering pleasures like a soaking tub, fireplace, or the whirlpool spa tub in the large Whirlpool Spa suite. The immaculately appointed lodgings feature timber floors and coastal themes, with courtyard garden views, alfresco dining and an outdoor fire pit.

Indulge yourselves with the in-house BlueFin restaurant Surprise Package with a delicious breakfast for two, loaded with local coastal cuisine.

Other special little luxuries to elevate your stay to a getaway fit for a celebrity, includes 24-hour valet parking, 24-hour room service, concierge service, and a fully equipped fitness center.

6. AC Hotel by Marriott Portland Downtown/Waterfront, ME – a stylish and fun design hotel located in the historic Old Port neighborhood of Portland, Maine

AC Hotel by Marriott Portland Downtown Waterfront, ME AC Hotel by Marriott Portland Downtown Waterfront, ME1

The hotel’s location is perfect. Opposite the Ocean Gateway Pier ferry terminal, it faces the Atlantic Ocean at Casco Bay and is surrounded by Portland’s vibrant art and cultural attractions.

The property showcases classic modern European design and every amenity to ensure a weary traveler’s comfort, or provide the perfect starting point for guests to pursue a Portland city discovery adventure with unique and exciting attractions close by in every direction.

The hotel even has its own cool tapas bar. There is a gym, and for your convenience, valet parking and a laundry. The modern, tastefully appointed guest rooms offer city views or harbor views.

7. Aloft Portland Maine – a cool, funky and creative hotel in Portland, Maine perfect for Millennials and Gen Zs

Aloft Portland Maine Aloft Portland Maine1

The Aloft Portland Maine boutique hotel, located on the working waterfront, reflects urban sophistication at its best. Its distinctive Art Deco design boasts whole street fronts of floor-to-ceiling windows overlooking the city and Portland harbor.

If you are seeking modern accommodation that not only welcomes children but your doggy friends as well, you must give this hotel some consideration.

Located as it is in the center of everything, including the bay, there is something thrilling to do, eat, experience or see close by for everyone in the family to enjoy, every day of your stay.

After a busy day, put the kids into Camp Aloft and enjoy dinner and drinks at the trendy WXYZ lobby bar or wind down with a game of billiards in the games room.

8. Haven on the Hill – a well-equipped hip and modern apartment near many great attractions

Haven on the Hill - Portland, Maine Haven on the Hill - Portland, Maine1

Located in a tranquil, leafy neighborhood in Portland’s East End, Haven on the Hill is a charming apartment, dating back to the 1890s.

It has been remodeled and modernized while still keeping reminders of a bygone era, like the elegant clawfoot tub, hardwood timber floors and sliding barn doors.

As well as the sweeping ocean views, the apartment’s appeal is its proximity to simply everything from award-winning restaurants, the Merrill Auditorium, the Portland Museum of Art, bakeries, coffee houses, shops and of course the harbor itself, all within walking distance. And the best thing is, that guests can even bring their dogs on vacation with them.

9. The Chadwick Bed and Breakfast – a charming and cozy B&B very popular amongst couples

The Chadwick Bed and Breakfast - Portland, Maine The Chadwick Bed and Breakfast - Portland, Maine1

This charming historic mansion is an 1890s Queen Anne-style house, located just a short walk from the Portland Museum of Art and the heart of the Old Port downtown shopping and cultural precinct.

The prestigious Chadwick BnB is also just a short drive from outdoor attractions including, boating, fishing and hiking in the spectacular Lakes Region and the Western foothills. Winter sports including snowmobiling, snowboarding and skiing, are also close by, during winter.

Pamper yourselves with a romantic weekend away at the Chadwick, enjoying all its delights including breakfast in the formal dining room or afternoon tea on the patio, and the garden with its fountain and a fire pit.

The inn has won awards for its progressive efforts to operate sustainably with green initiatives in waste management, reduced energy consumption and water conservation.

10. The Inn on Carleton – an upscale quirky chic stay situated on a tranquil street in Portland’s historic West End neighborhood

The Inn on Carleton - Portland, Maine The Inn on Carleton - Portland, Maine1

Located in the leafy Western Promenade Historic District, a restored 1860s grand Victorian-style building houses this stylish BnB. The 6 guest rooms feature elegant reminders of a bygone era with 4-poster beds, fireplaces and soaking tubs.

Added delights include the English-style garden where you can sit, relax and take tea or perhaps indulge in light conversation in the sitting room.

For that ultimate vacation indulgence, partake of a full English breakfast each morning on the terrace, seasonal of course. And for your convenience and comfort, the Inn provides a concierge service, free Wi-Fi, and room service.

It is just a short walk to the energetic Arts District, Old Port, and the waterfront with its shops, bars and eateries.

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