Figuring out where to stay in Portland, Maine is all about what part of the city you want to learn about first. This town has a rich history, and almost all of the attractions that you can visit can shed a bit more light on it.
Why You Should Visit Portland, Maine in 2023
Portland is known for many things. The city has a history that’s as deeply tied to the American Civil War as much as it is to tourism. As a testament to this, you can find dozens of lighthouses around the city and in close proximity from a time when fishing boats were a lot more plentiful.
As for the Civil War history, Portland, Maine has a number of locations like the Maine Military Museum, the Fifth Maine regiment hall, and the Eighth Maine hall.
All of these places have historical memorabilia that can teach tourists a little more about the most famous battles that were fought here. As such, the city should be on any Civil War history enthusiast’s bucket list.
Aside from the war buildings, Portland also has a lot of other interesting museums as well. There’s the Maine Narrow Gauge Railroad Co. & Museum and its display of steam engines, the Cryptozoology Museum and its strange exhibits on fictional animals, and many more.
There’s quite a lot to go through, and if you want to decide on where to stay in Portland, Maine, then your best bet would be to look through the attractions and find the ones that you’d like to have in close proximity.
The 5 Best Areas in Portland, Maine
All of the areas that we mention in our article have a specific attraction that they’re known for and that draws tourists in. If you’re wondering where to go in Portland, we’ve outlined the most important spots for you.
- Old Port: The vibrant nightlife hub of the city
- Downtown: The center of the city has a little bit of something for everyone
- Casco Bay Islands: Plenty of seaside restaurants and walking trails that you can explore
- East Portland: Home of many distilleries that you can tour
- South Portland: Plenty of interesting museums to explore
The Best Areas & Hotels in Portland, Maine
The city of Portland, Maine takes up a surface of around 70 square miles and has a population of nearly 70 thousand. Despite the multitude of attractions, this city remains rather small in terms of population.
Therefore, in a sense, Portland is unfortunately a rather empty city, and you’ll likely need to walk for quite a bit if you want to go from one attraction to the next.
The best idea would always be to stay in a hotel that’s located relatively close to attractions that you might want to visit. This leads us to the second issue. There aren’t all that many hotels in Portland as a whole.
Most of them are in the Old Port and Downtown areas, but you’re likely going to struggle actually finding a room outside of that region of the city.
We’ve covered the most attractive accommodation options in each of the areas that we mentioned and categorized them all by price and the type of services they offer. All you have to do is look through the article and decide on where you want to spend your time in the city.
1. Old Port
Old Port might just be the most well-known region of Portland, Maine. The name of this area comes from the old cobblestone streets that line it along with the accompanying old buildings that give off the same old-school vibe.
The architecture and the aesthetic of Old Port give tourists a good reason to come to this area. Moreover, the many souvenir shops ensure that you’ll have something to bring back home to commemorate your trip.
However, despite many people’s beliefs, the buildings are actually not the main attraction here. The main attractions of Old Port are the many vibrant restaurants, pubs, bars, and cafes that can be found on nearly every street corner.
This is the center of the nightlife in the city, and it’s the place for you if you’re looking to enjoy a nice cool drink in one of the lounge bars or if you want to rock out to some music in the clubs.
As you might expect from a nightclub district in a city, you’ll likely spend a bit more money here than in other parts of Portland. The drinks are generally a lot more expensive, and you’ll need to reserve a hotel in advance if you want to get a decent rate for your room.
Things to Do
- One of the best things to do in this area during the day is to go on one of the guided tours that show you some of the most historically significant buildings and streets.
- The pub crawl is a time-honored tradition in these parts, and with so many bars to choose from, everyone is likely going to take a different drinking path through Old Port.
- Visit some of the craft breweries that are located in Old Port and get a bit of behind-the-scenes knowledge on the distilling process.
- There’s a giant Victorian mansion in this area that’s a great exhibit for history buffs and people that just want to see what interior design was like back in the day.
Where to Eat
- Central Provisions serves great cocktails and entrees for when you want to have a drink and a nibble.
- The Grill Room & Bar is where you go if you want some BBQ with your beer.
- Luke’s Lobster Portland Pier offers a great catch-of-the-day menu.
Old Port Budget Hotels
- Hyatt Place Portland-Old Port comes with a flat-screen TV and a coffee maker in every room, as well as free shuttle services.
- Canopy By Hilton Portland Waterfront provides all of the guests with a free a la carte breakfast each morning, as well as free wifi throughout the property.
Old Port Mid-Range Hotels
- Hilton Garden Inn has a flat-screen cable TV, a refrigerator, and a microwave in every room, on top of the free breakfast buffet each morning.
- Portland Harbor Hotel comes with valet parking and a private garage where you can keep your car, and the rooms come with a sofa and a spa bath.
Old Port Luxury Hotels
- Canopy By Hilton Portland Waterfront gives you a choice of an American and an a la carte breakfast each morning, and all of the rooms come with an AC unit, a safety deposit box, and a coffee machine.
- The Press Hotel comes with an in-house restaurant where guests can enjoy a nice meal, a fully-equipped fitness center that they can use, and there’s free wifi throughout the property.
Downtown is another pretty popular place in Portland. Here, you’ll find plenty of great restaurants where you can enjoy a meal as well as a lot of cafes.
There are also plenty of boutiques if you’re looking to go on a shopping spree and maybe freshen up your wardrobe a bit. In that regard, visiting the shopping malls is also a good idea.
There’s also a bit of history here in the form of the old City Hall building that was constructed all the way back in 1912. Lincoln Park, on the other hand, might not be as old as City Hall, but it still dates back more than half a century, too.
If you’d like to spend a relaxing day in the great outdoors, the park’s fountains and its natural beauty are a great draw. Downtown Portland is also home to both the Children’s Museum and the Portland Museum of Art.
As its name might suggest, the Children’s Museum features artworks created by young talented artists. On the flip side, the Museum of Art has exhibits that are a bit more obscure, so that’s worth checking out as well if you’re partial to abstract art.
Downtown is a pretty busy location in Portland, which means that you’ll usually find the streets filled with tourists and residents alike. Unfortunately, this also means that it’ll be a bit difficult to actually get a decent table anywhere on most nights.
Things to Do
- Seek out a bit of cultural enrichment for both you and your kids by paying a visit to the Children’s Museum and the Portland Museum of Art.
- Visit the Maine Historical Society and the Wadsworth-Longfellow House to learn a bit more about the story of one of the most notable poets that ever came out of Portland.
- The Merrill Auditorium usually has an interesting play or show that you can watch every day or at least every second day.
- Go down to Monument Square and check out the famous Portland Soldiers and Sailors Monument.
Where to Eat
- David’s Restaurant is the best place to go if you’re in the mood to try some of their many fish dishes.
- UNION Restaurant is a chic place where you can get a cocktail and a bite to eat.
- Slab Sicilian Street Food is where you go if you want a slice of pizza.
Downtown Budget Hotels
- The Westin Portland Harborview provides all of the guests with access to the on-site fitness center, as well as rooms that come with a cable TV and coffee maker.
Downtown Mid-Range Hotels
- Holiday Inn Portland-By the Bay comes with free wifi in every room, an indoor pool that guests can use, and an in-house restaurant where you can eat.
- Courtyard by Marriott Portland has a front desk that’s always available, a flat-screen TV and free wifi in every room, and even an on-site fitness center.
Downtown Luxury Hotels
- The Press Hotel has an in-house restaurant and fitness center that guests can take advantage of, an AC unit and a refrigerator in every room, and free wifi and shuttle services.
3. Casco Bay Islands
Portland may not have as many islands as Hawaii, but the ones that it does have still offer quite a few interesting attractions.
The actual number of islands is six, but considering the fact that Ram Island only has a lighthouse in terms of tourist destinations, it’s safe to say that you’ll be more interested in the other five.
Peaks is the largest island out of the bunch. Here you’ll find plenty of Civil War memorial halls that were built back in the 19th century. The island also used to be home to many theaters, bars, and even an amusement park, and you can see all of these sights by taking a walking tour.
The unpaved roads mean that you’ll need to leave your car near a ferry parking spot, but you can simply walk or take the more fun approach and rent out a golf cart for the day.
Speaking of golf, Chebeague Island has a great golfing course where you can go and play the 9-hole field. Moving on, the biggest attraction on Great Diamond Island would undoubtedly have to be the historic Fort McKinley, where you can get a guided tour almost every hour.
If you’re not into history or golf, Long Island and Cliff Island are both great destinations for anyone looking for some good hiking trails. The obvious problem with visiting these islands is the ferry that you’ll need to take to get from one to the other.
Add to that the fact that you’ll need to get a hotel somewhere in the main city, and you get a series of small annoyances that most people don’t want to put up with.
Things to Do
- Go to the Chebeague Island golf course and either learn how to properly swing a club or get a bit of practice in if you know how to play the game already.
- Explore the many hiking trails that can be found throughout the islands and see the natural beauty that you can find on them.
- Take a tour and learn a bit more about all of the abandoned facilities and amusement parks in Peaks Island.
- Visit the Fifth Maine regiment hall and the Eighth Maine hall, both of which are sort of like museums that display exhibits from the Civil War.
Where to Eat
- Island Lobster Company offers a great catch-of-the-day menu with plenty of seafood dishes.
- Il Leone is a great place to grab a bite to eat while strolling through the island.
- The Cockeyed Gull Restaurant is where you go if you want some breakfast.
Casco Bay Islands Budget Hotels
- The 8th Maine Regiment Lodge and Museum offers simple accommodations but with a beach-side location and a fantastic view.
- Inn at Diamond Cove comes with an outside pool that guests can use at any time, and the hotel itself is located right in the middle of all of the shops, cafes, and restaurants in town.
Casco Bay Islands Mid-Range Hotels
- DoubleTree by Hilton Portland comes with an indoor heated pool. Free wifi and parking for all of the guests and all of the rooms come with a flat-screen TV.
Casco Bay Islands Luxury Hotels
- Aloft Portland Maine provides all of the guests with a complimentary breakfast each morning, which includes a vegetarian option, and the hotel itself comes with a 24-hour front desk, as well as free wifi and a flat-screen TV in every room.
- Portland Regency Hotel & Spa has an in-house restaurant where guests can choose from a large assortment of American-styled seafood dishes, as well as a fitness center, a full-service spa, steam rooms, and a hot tub.
4. East Portland
The area of East Portland that we’re covering encompasses both the East End and East Bayside. This area is known for both the Eastern Promenade and Fort Allen Park.
You can enjoy a bit of peace and quiet and beautiful views of the bayside on both trails, which also feature historic monuments. One of the most notable attractions in East Portland is the Maine Narrow Gauge Railroad Co. & Museum.
This is a pretty unique landmark that showcases the famous narrow railway that was built in Maine back in the early portion of the 19th century. The trains themselves are pretty small so that they can fit on the narrow rails that are only two feet apart, so there are some fun exhibits to see here.
East Bayside, on the other hand, is much more well-known for its multiple distilleries that you can tour if you want to learn more about beer making. Who’s up for samples in the in-house bar?
Once you’ve had your fill, you could move on to the art galleries, where you can see both photography and paintings of the more abstract variety.
You also have the Mayo Street Arts theater, where you can catch a show when you’re in the mood for dressing up and a night out in town. That said, the biggest issue with this part of the city is that it doesn’t really have much character.
Most other sections of Portland are known for a specific attraction or have something going for them. The East Side has a lot of fun things that you can do, but except for the distilleries, none of the places that you can visit are all that amazing.
Things to Do:
- Visit the Maine Narrow Gauge Railroad Co. & Museum and look through the locomotives that are on display there.
- Book a tour of the Belleflower Brewing Company, the Goodfire Brewing Company, or some of the many other distilleries in this region.
- Go to some of the art galleries in this area and check out the different exhibits that display both photography and abstract paintings.
- Take a walk down the Eastern Promenade and check out the view of the bay, as well as the historic monuments that can be found all over the place.
Where to Eat
- Izakaya Minato offers Japanese dishes, sake, and even several cocktails that you can try.
- Ribollita is where you go if you’re interested in trying some traditional Italian dishes.
- Portland Zoo is where you go if you want a stiff drink or a nice cocktail.
East Portland Budget Hotels
- Black Elephant Hostel offers pretty decent accommodations for the price range, and all of the guests get access to a fully-equipped kitchen and free wifi.
- Hampton Inn Portland provides you with rooms that have an AC unit, a cable TV, and free wifi, as well as a complimentary breakfast each morning.
East Portland Mid-Range Hotels
- Hilton Garden Inn Portland comes with a business center that’s always open, an indoor pool that guests can use, and a fully-equipped fitness center with everything that you need to work up a sweat.
- AC Hotel by Marriott Portland has a flat-screen TV and a mini-fridge in every room, and you get a grab-and-go breakfast in the lobby each morning.
East Portland Luxury Hotels
- Residence Inn Portland provides all of the guests with 37-inch LCD TV in every room, an indoor pool with a hot tub, a fitness center that they can work out in, and free wifi throughout the property.
5. South Portland
The first thing that you might want to do when you get to South Portland is visit the Maine Mall. Here, you’ll find plenty of different shops that you can visit and food courts that you can try out.
There are also a few playgrounds where you can leave your kids and let them run around while you grab a coffee at a nearby cafe. However, the big draw of South Portland is definitely Willard Beach.
It might not quite be as large or attractive as the beaches you’ll find in San Diego or Miami, but it’s still an ideal place for sunbathing and maybe even a bit of swimming or volleyball if the weather allows it.
Other attractions include the Liberty Ship Memorial and the Spring Point Ledge Lighthouse, which is also known as “that little lighthouse that’s shaped like a spark plug.”
You can also visit the Maine Military Museum, the South Portland Historical Society Museum, and the International Cryptozoology Museum, all of which have interesting exhibits.
The surprising thing about South Portland is that even though it’s the largest area of the city, it’s sparse in terms of bars, restaurants, and even hotels. This means that you’ll need to walk a fair distance if you want to get a drink, and you might even have trouble finding accommodations here.
Things to Do
- Go to the Maine Military Museum and check out some of the memorabilia that was saved from the Civil War.
- Take an umbrella and some sunscreen, and spend an entire day just chilling out and relaxing on Willard Beach.
- The Cryptozoology Museum aims to prove the existence of creatures like Bigfoot and the Loch Ness Monster, and there are some pretty fun exhibits that you can check out,
- Take a walk by the bay, check out the Spring Point Ledge Lighthouse, and maybe even visit the Calvary Cemetery.
Where to Eat
- Docks Seafood is a simple restaurant where you can get some sandwiches.
- Saltwater Grille is a great place to get some seafood specialties with a great view of the bay.
- Scratch Baking Co. is where you go if you’re in the mood for some pastries.
South Portland Budget Hotels
- Courtyard by Marriott Portland comes with free parking, an indoor pool that all of the guests can use, and a fitness center that’s pretty well equipped.
- Tru By Hilton Portland provides all of the guests with rooms that have a 55″ flat-screen TV, as well as free parking and wifi.
South Portland Mid-Range Hotels
- Hampton Inn Portland-Airport comes with an on-site fitness center, an indoor heated pool, and a complimentary breakfast each morning.
- Holiday Inn Express South Portland has a room with a flat-screen cable TV, a fitness center that all of the guests can use, and free wifi and parking.
South Portland Luxury Hotels
- Home2 Suites By Hilton Portland provides you with a continental breakfast every morning in the lobby, a room with a flat-screen satellite TV, and a front desk that’s always available.
- DoubleTree by Hilton Portland offers free wife and a flat-screen cable TV in every room, as well as an indoor heated pool, an on-site restaurant, and a front desk that’s on-call 24/7.
So, Where Should You Stay in Portland?
|🍺 Best Area for Nightlife||Old Port|
|✅ Best Area to See Everything||Downtown|
|🍽️ Best Area for Restaurants||Casco Bay Islands|
|🍷 Best Area for Distilleries||East Portland|
|🖼️ Best Museums||South Portland|
As we mentioned before, Portland is a relatively small city in terms of both the population and the area that the city itself covers. However, there are still plenty of sights to see, and if you’re a bit confused about where you should stay, then here’s all you really need to know.
Anyone that prefers to spend their trips drinking or partying will definitely want to visit Old Port and check out all of the different bars.
Downtown has many different attractions, and you can choose to visit one of the many entertainment venues like the cinemas and the theaters or just enjoy a drink or a meal in one of the many restaurants and cafes.
South Portland has the most interesting museums in the city, and you’ll find both historical sites as well as interesting exhibits. But every area is beautiful, so you really can’t go wrong with any of the areas on this list. Happy travels!