Top 9 Cool and Trendy 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 trendy hotels in Portland, Maine (in no particular order, they’re all awesome)

Best For Boutique

Blind Tiger Guest House

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

Discover the allure of Portland, Maine at the captivating Blind Tiger Guest House. This extraordinary boutique-style accommodation embraces the rich history of the 19th century, effortlessly blending timeless elegance with contemporary comfort. Prepare to be enchanted as you step into this meticulously restored Federal-style mansion, where every corner exudes regal charm.

Nestled near the enchanting Old Port, a bustling waterfront district bursting with life, the Blind Tiger Guest House offers unrivaled proximity to the vibrant heart of Portland. Stroll through the charming streets, immersing yourself in the eclectic array of shops, galleries, and enticing culinary havens. Venture further to behold the majesty of the Portland Head Light, the oldest lighthouse in Maine, or marvel at the architectural splendor of the Victoria Mansion, a true testament to Italianate design.

Returning to the sanctuary of the inn, find solace in the inviting embrace of various intimate common areas. Unwind amidst the refined ambiance of the billiard room, the sun-drenched conservatory, or the serene enclosed garden and sun terrace. A delectable breakfast awaits you at “The Pantry,” where freshly baked pastries, succulent fruits, aromatic coffee, and invigorating tea tempt your palate.

Indulge in the opulence of spacious rooms and suites adorned with 19th-century accents, luxurious linens, and tastefully designed private bathrooms. Select accommodations even feature cozy wood-burning fireplaces, beckoning you to relax with a captivating novel or savor a glass of wine. Stay connected with complimentary Wi-Fi throughout your stay, seamlessly blending modern convenience with timeless indulgence.

Prepare for an unforgettable journey through Portland, where the Blind Tiger Guest House transcends the ordinary to offer an extraordinary experience. Unveil the secret that whispers through the city and reserve your room today, creating memories that will forever linger in your heart.


Restored 19-century charm

Built-in fireplaces for a comfy vibe

Expert guides to help you explore the Portland

Complimentary breakfast at The Pantry


Can be crowded on weekends

Windows are old

Best For Millennials and Gen Zs

Canopy By Hilton Portland Waterfront

Canopy By Hilton Portland Waterfront Canopy By Hilton Portland Waterfront1

Are you ready for a hip, trendy, and very Instagrammable hotel experience in Portland, Maine? If so, you will love the Canopy By Hilton Portland Waterfront, a refined and stylish accommodation that caters to partying Millennials and Gen Zs. 

This hotel 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.

The hotel features a contemporary design with a nautical theme, inspired by the local culture and history. The rooms and suites are spacious and comfortable, with custom furnishings, local artwork, complimentary Wi-Fi, and 55-inch TVs. You can also enjoy the signature Canopy bed, a Nespresso machine, a mini-fridge, and a filtered water station in your room.

But 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 breathtaking panoramic views over downtown Portland and out across the bay. Luna also offers a seasonal menu of locally sourced small plates and craft cocktails that will tantalize your taste buds.

The hotel also has a fitness center, a business center, a meeting room, and a private dining room for your convenience. You can also enjoy a complimentary artisanal breakfast each morning at Salt Yard Cafe and Bar, which also serves fresh and healthy lunch choices and classic cocktails with a local twist.

The Canopy By Hilton Portland Waterfront is more than just a hotel. It is a destination that will make your stay in Portland fun, memorable, and Instagram-worthy. Don’t miss this opportunity to book your room today and discover why this hotel is one of the coolest places in town.


Industrial-chic hotel

Pet-friendly up to 75 pounds

Premium location for sightseeing

Spacious rooms with local artwork


Extra-soft beds

Valet parking can be pricey

Best For Unique

The Press Hotel, Autograph Collection

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

If you are a fan of chic and trendy hotels with a touch of history, you will love the Press Hotel, Autograph Collection. This grand hotel inhabits a classic heritage brick building that used to be the home of the Portland Press Herald, the state’s largest newspaper. The hotel pays homage to its past with a newspaper theme that is evident in every detail, from the décor to the service.

Situated in the heart of the bustling Old Port district, a vibrant tapestry of shops, restaurants, and attractions awaits your exploration. Marvel at breathtaking city views from your room or the rooftop terrace, where the skyline meets the harbor in a mesmerizing tableau.

There is no shortage of style in the rooms and suites, reminiscent of a 1920s press editor’s office. Vintage accents, including a journalist’s desk, typewriter, and newspaper references, adorn the decor. Enjoy luxurious features like marble bathrooms, plush bedding, complimentary Wi-Fi, 55-inch TVs, Nespresso machines, mini-fridges, and filtered water stations.

Immerse yourself in the hotel’s captivating ‘letterpress art wall,’ a mesmerizing homage to old newspaper offices. Discover the hotel’s art gallery, showcasing the talent of local artists.

Delight in an array of amenities, from dining at UNION, a restaurant serving creative dishes with local ingredients, to unwinding at Inkwell, the lobby bar offering handcrafted cocktails and light bites. Stay active in the fitness center, tend to business needs in the business center, or book meeting rooms for your events.

The Press Hotel, Autograph Collection is more than just a hotel. It is a story that will captivate you and make you feel part of Portland’s history and culture. It’s clear to see why this is a hit with keen travelers!


Newspaper theme throughout the hotel

Rooms inspired by 1920s designs

Art Gallery featuring regional artists' works

Dishes made from local ingredients


Bar closes before midnight

Few unfriendly staff members

Best For Couples

The Francis

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

Immerse yourself in the warm embrace of personalized service and local charm at The Francis—a delightful boutique hotel nestled in Portland’s prestigious Parkside neighborhood within the vibrant West End Arts district. This charming 19th-century mansion is a testament to a bygone era, with its prime location near the Portland Museum of Art and the serene Deering Oaks Park.

Explore nearby attractions, such as the historic Old Port district with its waterfront shops, restaurants, and galleries, the scenic Casco Bay Islands accessible by ferry, and the breathtaking Portland Head Light, Maine’s oldest lighthouse.

The spacious rooms and suites offer comfort and style, featuring plush bedding, marble bathrooms, complimentary Wi-Fi, and smart TVs. Some accommodations boast fireplaces, balconies, or soaking tubs.

Indulge in a host of amenities, including an in-house spa offering massages and facials, and the farm-to-table restaurant Bolster Snow & Co., serving creative dishes with local ingredients. Unwind in inviting lounges, sip a drink, and savor a snack.

The hotel actively supports the community through partnerships with organizations like Indigo Arts Alliance, Mayo Street Arts, and campaigns such as Full Plates Full Potential’s ‘Feed Kids’.

At The Francis, you’ll find a welcoming home, immersed in local culture and hospitality, ensuring an unforgettable stay in Portland. Book your room today and discover why this hotel is a top choice in town.


A local boutique-style hotel

Uniquely designed rooms

Mini bars with locally made treats

Central location


No coffee-makers in the rooms

No on-site breakfast

Best For Location

Portland Harbor Hotel

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

Escape to the refined elegance of the Portland Harbor Hotel, a charming boutique gem nestled in downtown Portland, ideal for a romantic retreat. This exquisite property holds the distinction of being the only Triple A-rated 4 diamond hotel in Old Port, ensuring exceptional service and unparalleled comfort.

Positioned as an ideal starting point, the hotel grants easy access to nearby attractions. Immerse yourself in art at the Portland Museum of Art, showcasing captivating works by both local and international artists. Embark on a delightful excursion to the Casco Bay Islands, reachable by ferry or kayak, and discover their scenic allure. Gaze upon the mesmerizing vistas from the Portland Breakwater Lighthouse, capturing the harbor’s beauty and the vastness of the ocean.

Adorned with a beautiful red-brick exterior and an elaborate portico, the hotel welcomes you with an inviting ambiance. Step inside to discover a cozy haven boasting a fireplace, a library, and a tranquil garden courtyard. The spacious rooms and suites exude luxury, featuring timber floors, coastal-inspired décor, and enchanting views of either the garden or the cityscape. Indulge in additional relaxation with soaking tubs, fireplaces, or whirlpool spa tubs available in select rooms.

A host of amenities and services await, ensuring an unforgettable stay. Tuck in to delectable coastal cuisine at BlueFin, the hotel’s renowned restaurant, where a complimentary breakfast for two awaits each morning. Enjoy the convenience of 24-hour valet parking, 24-hour room service, a dedicated concierge, and a fully equipped fitness center.

The Portland Harbor Hotel beckons you to embark on a romantic escapade, where you can indulge in the local culture, savor delectable cuisine, and create cherished memories in the heart of Portland. Secure your reservation today and unveil why this extraordinary haven reigns as one of the premier choices in town.


Red-brick exterior located near the Portland Waterfront

Rooms with a cozy and nautical vibe

Complimentary Starbucks drip coffee in the mornings

A peaceful garden courtyard


Paid parking

Bar drinks are pricey

Best For Views

AC Hotel by Marriott Portland Downtown/Waterfront, ME

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

Step into the world of chic and vibrant design at the AC Hotel by Marriott Portland Downtown/Waterfront, ME—a captivating oasis nestled in the historic Old Port neighborhood of Portland, Maine. Embracing classic modern European influences, this hotel effortlessly combines style and functionality, offering an array of amenities to ensure your utmost comfort and convenience.

Boasting a prime location opposite the Ocean Gateway Pier ferry terminal, it embraces Atlantic Ocean vistas in Casco Bay and finds itself surrounded by Portland’s lively art and cultural attractions. Discover nearby gems like the Portland Museum of Art, housing a captivating collection of local and international works. Immerse yourself in the architectural grandeur of the Victoria Mansion or ascend the historic Portland Observatory for sweeping city and harbor views.

You’ll find yourself in a contemporary oasis adorned with nautical touches, paying homage to the local culture and heritage. Indulge in the comfort of spacious rooms and suites adorned with custom furnishings, local artwork, complimentary Wi-Fi, and 55-inch TVs. The signature AC bed awaits, accompanied by amenities such as a Nespresso machine, mini-fridge, and filtered water station.

Place your order from the menu and explore Spanish-inspired fare and libations at the hotel’s lively tapas bar. Maintain your fitness routine in the well-equipped fitness center, attend to business needs in the convenient business center, or reserve a meeting room for your events. Enjoy the ease of 24-hour valet parking, room service, concierge service, and efficient laundry facilities.

If you’re keen to try something different then this could be everything you want and more, so make your booking today!


Classic modern European style

Contemporary minimalist rooms

Some rooms have harbor views

European-inspired breakfast


Parking can be slightly expensive

Low-quality toilet paper

Best For Trendy

Aloft Portland Maine

Aloft Portland Maine Aloft Portland Maine1

Unleash your sense of cool and embrace creativity at the Aloft Portland Maine—a vibrant, funky boutique hotel in the heart of Portland, Maine, tailor-made for Millennials and Gen Zs. Located on the bustling working waterfront, this urban retreat exudes a distinctive Art Deco charm, with expansive floor-to-ceiling windows that frame panoramic views of the city and the mesmerizing Portland harbor.

Centrally located, the hotel grants easy access to a range of activities, from kayaking, sailing, and fishing in the bay to exploring the historic waterfront district of the Old Port, home to shops, restaurants, bars, and galleries. Discover the Children’s Museum & Theatre of Maine, an engaging and educational haven for kids, or be enchanted by the performances of the renowned Portland Symphony Orchestra at the Merrill Auditorium.

Welcoming both children and furry friends, the hotel’s Arf: Animals are Fun program ensures a delightful stay for your pets, providing them with a cozy dog bed, a bowl, toys, and treats.

Unwind after a busy day by treating the kids to Camp Aloft, providing air mattresses, kid’s bedding, and food and beverage vouchers. Modern and stylish, the rooms and suites offer city or harbor views, plush platform beds, LCD TVs, custom Aloft bath amenities by Bliss Spa, and refreshing walk-in showers with rainfall showerheads. Enjoy complimentary Wi-Fi, Nespresso machines, mini-fridges, and filtered water stations.

Indulge in dinner and drinks at the trendy WXYZ lobby bar, where live music sets the mood. Engage in a game of billiards or maintain your fitness routine in the well-equipped fitness center.

For something a little different and a hotel that takes care of your needs, this hotel is all that you need!


A cool and funky vibe for young ones

Fitness Center to keep you fit

On-site restaurant offering breakfast and dinner

Camp Aloft specially designed for kids


TV needs more options

Inferior bathroom mirror

Best For Self-catering

Haven on the Hill

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

You’re certain to love the well-equipped embrace of Haven on the Hill—a hip and modern apartment nestled in Portland’s serene East End. This charming retreat, dating back to the 1890s, effortlessly blends modernity with reminders of a bygone era, showcasing elegant clawfoot tubs, hardwood timber floors, and sliding barn doors.

The apartment’s allure lies in its proximity to an array of attractions, all within walking distance. Discover award-winning restaurants, the esteemed Merrill Auditorium, the Portland Museum of Art, charming bakeries, cozy coffee houses, enticing shops, and the captivating harbor itself. Venture to nearby gems like the historic Portland Observatory, offering panoramic city and harbor vistas, or immerse yourself in the interactive wonders of the Children’s Museum & Theatre of Maine. Delight in the melodious performances of the renowned Portland Symphony Orchestra at the Merrill Auditorium

Featuring two bedrooms, a bathroom, a living room, a dining area, and a fully equipped kitchen, the apartment offers ample space for your comfort. Unwind on the balcony, reveling in sweeping ocean views and the enchanting sunset. Indulge in modern amenities such as a flat-screen TV with cable channels, complimentary Wi-Fi, luxurious bed linen, towels, and custom bath amenities.

Welcoming your furry friends, this pet-friendly haven ensures their companionship throughout your stay. Enjoy the convenience of free private parking on site.

For anyone looking for a unique escape then this is all you need. You can explore a private escape that can become a family getaway or a romantic break. Whatever you want, this accommodation is certain to take care of it all.


A rustic look with modern furniture

Spacious warm rooms

Variety of attractions nearby



No on-site pool

Steep staircase

Best For Bed and Breakfast

The Chadwick Bed and Breakfast

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

Nestled in the heart of Portland’s Old Port downtown district, the Chadwick Bed and Breakfast awaits, charming and cozy—a favorite among couples seeking an idyllic retreat. Housed in a historic Queen Anne-style mansion dating back to the 1890s, this captivating B&B is just a short stroll from the Portland Museum of Art and the vibrant shopping and cultural precincts.

Venture out to nearby attractions, such as the historic Portland Observatory, which treats you to panoramic city and harbor vistas. Admire the opulent beauty of the Victoria Mansion, showcasing exquisite Italianate architecture and design. Immerse yourself in the captivating melodies performed by the renowned Portland Symphony Orchestra at the Merrill Auditorium.

Discover the charm of four exquisitely appointed guest rooms, each boasting a private en-suite bathroom, a flat-screen TV, a fireplace, and custom bath amenities. Luxuriate in plush bedding, enjoy complimentary Wi-Fi, and relish views of either the serene garden or the bustling cityscape.

Wake up to a delectable homemade breakfast each morning, offering American, vegetarian, or vegan options. Delight in the inviting ambiance of the formal dining room or enjoy your meal on the patio, overlooking the garden’s enchanting fountain and inviting fire pit. Indulge in afternoon tea or coffee accompanied by freshly baked treats.

The Chadwick Bed and Breakfast has earned accolades for its progressive commitment to sustainable operations, exemplified through green initiatives in waste management, reduced energy consumption, and water conservation. So, if you want a stay with a difference and want to create memories that last a lifetime, this is certain to give you everything you’re looking for.


Modern accommodations with a warm ambiance

Nearby White Mountains of New Hampshire

20 Minute Walk to The Old Port

Daily homemade Breakfast


Limited parking

Some rooms can be Noisy

Top-Rated Hotels in Portland Ranked 

The following table enlists a detailed ranking of the top 9 cool hotels in Portland. 

Hotel NameLocationPrice Range (per night)Fitness FacilitiesDistance to AttractionsNearby Restaurants
Blind Tiger Guest House163 Danforth Street$770Yes2.11
Canopy By Hilton Portland Waterfront9 Center Street, Portland$500-$985Yes1.43
The Press Hotel119 Exchange Street$549-$577Yes1.03
The Francis747 Congress Street$368-$391No2.23
Portland Harbor Hotel468 Fore Street, Portland$440-$588Yes1.22
AC Hotel by Marriott Portland Downtown/Waterfront158 Fore Street$362-$566Yes1.43
Aloft Portland Maine379 Commercial Street$380-479Yes1.73
Haven on the Hill70 Waterville Street 2$640No1.42
The Chadwick Bed and Breakfast140 Chadwick St$359No1.3
The Inn on Carleton46 Carleton St$458-$499No2.42