Where to Stay in Portland, Maine

June 28, 2022

Portland, Maine has been making the hot lists in recent years and I know how overwhelming it can be to find just the right place to stay when planning your trip. I grew up and currently live and work in the Great Portland area so who better to give suggestions on where to stay? Here are my top picks!

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The Old Port

The Portland Harbor Hotel

This hotel is located in the heart of the Old Port and is within walking distance to great restaurants, museums and bars. There is also onsite parking which is nice to have in this busy area. Rooms are comfy and have a homey feel. Andrew and I have stayed here twice on our wedding night and for an anniversary. The staff are super friendly and the bar/restaurant is excellent.

The Press Hotel

This hotel was once the Gannett Building, the headquarters of the Portland Press Herald—the state’s largest newspaper. They pay homage to the building’s history by having typewriters at every turn, artistic nods to typesetting, and quotes from Maine literary luminaries. The onsite bar is a favorite stop for locals who are attending a show at The Merrill Auditorium across the street. Located at the very top of the Old Port it’s within walking distance to shops and historic attractions like The Longfellow House.

The Portland Regency Hotel

This hotel ,located in a 19th Century armory building, is a landmark in the Old Port. This building is rich in history and you can read all about it here. Rooms are comfy and inviting and the staff are super friendly. The bar downstairs serves up fantastic cocktails and lively conversations. Old Port shops and attractions are just steps away.

The West End/Art District

Blind Tiger Guest House

This Inn is housed in a 1823 Federal style mansion with a rooftop cupola. There’s a conservatory, a sitting room and a billiards room, as well as an enclosed garden. It’s like the game of Clue! Just a short walk from the Portland Museum of Art and a mile from the restaurants, bars and boutique shops of the Old Port.

The Westin Portland Harborview

This is really the only big chain hotel that you’ll see on this list. I included it because it’s a Portland landmark and full of history. Offering views of Portland Harbor, this upscale hotel dates back to 1927 and is literally across the street from Portland Museum of Art and The State Theatre. Rooms are comfy and there is a parking garage right next door. The Top of the East Lounge has wonderful panoramic views of Portland and Casco Bay from the 15th floor. The hotel is easy to spot, just look for the iconic Eastland rooftop sign.

The East End

The Best Bower

This guesthouse is situated alongside the Portland Observatory, one of Portland’s most beloved landmarks. The property has six spacious guest rooms each unique in layout and a shared kitchenette with a microwave & compact convection oven, dishwasher, full size refrigerator and ice machine. Hang out in the terraced courtyard after a day of exploring the city. You will be within walking distance to local breweries & distilleries, galleries & museums, boutique shopping, amazing restaurants, and the Eastern Promenade.

The Black Elephant Hostel

Don’t turn your nose down at a hostel! They aren’t just for broke college kids. Hostels offer a clean, safe place to stay that doesn’t break the bank. The less you spend on accommodations the more money you can spend on your experiences while traveling. Hostels have a lot of shared spaces which gives you that sense of community and that is great if you are solo traveling. This hostel offers both private rooms and shared bunks. There are plenty of common spaces but there are also rooms that have their own bathrooms and kitchens. The property is in a great location, within walking distance to the Old Port and Casco Bay Lines. Fun fact: My aunt used to live on the first floor when it was still an apartment building. It was turned into this hostel only a few years ago.

I hope this helps when you are planning your trip to Portland. These accommodations are all on the peninsula because if I were staying in Portland that’s where I would want to be 🙂

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