Where to Stay in Portland, Maine

SD › Best Places to Stay in Portland, Maine
Updated: March 26, 2021
By Santorini Dave

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The Best Areas to Stay in Portland

Portland skyline as seen from Casco Bay with the Old Port filled with boats. Downtown sits directly behind the Old Port just a few blocks away. The steeple belongs to the Cathedral of the Immaculate Conception and roughly marks the divide between Downtown and the Old Port; and the East End and Munjoy Hill.

Portland, Maine is a small but lively city by the sea, where the sounds and smells of the ocean permeate every neighborhood. Jutting east into Casco Bay, Portland is surrounded on three sides by water, so the city’s life and livelihood have always been tied to the ocean. And while the city has expanded to the north and west on the mainland, Portland’s heart and soul still reside squarely on the peninsula–and specifically around the Old Port.

Per the name, Old Port is a compact seaside neighborhood where brick warehouses line the narrow streets, fishing boats tie up to wooden piers, and salty marketeers hawk the catch of the day. Nowadays, there are also plenty of seafood restaurants, boat tours, and marine-themed souvenir shops, making Old Port the main draw for visitors to Portland. Just a few blocks inland, the historic Old Port morphs into the more modern Downtown, home to the city’s best museums as well as most hotels. These two overlapping neighborhoods dominate the peninsula and contain the bulk of the attractions for visitors to Portland.

The outer edges of the peninsula are known appropriately as the West End and the East End (the latter also called Munjoy Hill). These are mostly residential areas, with graceful mansions sitting atop the bluffs, overlooking the Fore River in the west and Casco Bay in the east. These quieter areas are still within striking distance of Downtown and Old Port attractions.

That said, the most compelling attraction around Portland may be the spectacular seacoast of Southern Maine, replete with beaches and boats and lighthouses and lobster. In Portland, it is possible to get more of a seaside resort experience, but still have easy access to the city. One option is Cape Elizabeth, which is a short drive south of Portland. The picturesque residential area is home to the landmark Portland Head Light as well as some recommended resorts and plenty of vacation rentals. For a true Maine experience, visitors can stay on one of several islands in Casco Bay, exploring the islands by bike and commuting to Portland by ferry.

The Best Places to Stay in Portland

Lobster boats at the Old Port in Portland, Maine

Lobster boats in a line in the Old Port, the historic heart of the city. Fishing boats still dominate the piers, shared with ferries and tour boats.

Best Areas in Portland for…

The charming pier on Old Orchard Beach, Maine.

Old Orchard Beach, just south of Cape Elizabeth, is a favorite with families for its sandy beach, busy pier, and nostalgic, beachside amusement park.

  • Best Neighborhood in Portland for History & Sightseeing: Old Port
    Portland’s sights are strewn across the city, from the museums and galleries Downtown to the Victorian mansions in the West End to Fort Williams and Portland Head Light on Cape Elizabeth. By contrast, the Old Port does not contain many museums or monuments, but the neighborhood itself is designated as the Waterfront Historic District, its cobblestone streets and redbrick architecture still evoking the 19th century when it was built. As a result, Old Port is the best neighborhood to experience the historic roots of this seaside city, even if it’s necessary to visit the other neighborhoods for more traditional sightseeing.
  • Best Neighborhood in Portland for Dining: Old Port
    In Portland, dining means seafood, and seafood means the Old Port. The historic seaside fishing district is packed with restaurants, most serving fish, lobster, oysters, and other sea creatures, fresh off the boat. Fish shacks and upscale restaurants line the docks that reach out into Casco Bay, offering a perfect waterside setting to feast on les fruits de mer. Away from the docks, there are more places to indulge on everything ranging from coffee and donuts in the morning to modern American locavore cuisine by night. Local favorites include Holy Donut, Luke’s Lobster, Eventide Oysters, Central Provisions for small plates, and Fore Street for roasted deliciousness.
  • Best Neighborhood in Portland for Nightlife: East End, Old Port
    For a small city, Portland has a vibrant brewing culture, showing up on most lists of the country’s best beer cities. In Portland, beer drinkers will not find a more welcoming destination than the East End (including Munjoy Hill and nearby East Bayside). The edgy neighborhood is home to no less than seven craft breweries, including the well-known Shipyard Brewing Co., local favorite Rising Tide Brewing Co.., and up-and-comer Lone Pine Brewing Co. For a more diverse after-hours scene, myriad pubs and clubs are tucked into the basements and courtyards of the Old Port, some hosting live music, dance parties, and even comedy clubs. Maine Brew Bus offers drinking tours of both neighborhoods.
  • Best Neighborhood in Portland for First Time Visitors: Downtown
    Downtown Portland is not the most atmospheric part of the city, but it does offer several advantages for first-time visitors. It is a vibrant commercial district, with plenty of restaurants and nightlife in the immediate area, not to mention the bulk of the city’s museums and theaters. It is centrally located, offering easy access to other neighborhoods by car or by bus; the Old Port is just a few walkable blocks away. And, it contains the greatest selection of hotels in the city, guaranteeing a comfortable stay in the right price range.
  • Best Neighborhood in Portland for Romance: West End
    Spend the day strolling along the lovely Western Promenade, taking in glorious views that stretch all the way to the White Mountains, and spend the night in a gracious Victorian-era mansion, relishing historic and artistic touches. After the Great Fire of 1866, the West End’s traditional wood-framed houses were replaced with stately brick homes, mostly Victorian High Gothic and Queen Anne styles, which now line the tree-shaded streets. Some of these beauties have been converted into period-decorated B&Bs and art-filled boutique hotels, offering a perfect place for lovers to bed down for a romantic weekend. The immediate neighborhood is short on restaurants, so for dinner, we recommend a walk to the Old Port, hand-in-hand and under star-filled skies, of course.
  • Best Neighborhood in Portland for Families: Cape Elizabeth, Casco Bay Islands
    Families will have some fun in Portland – visiting the Children’s Museum & Theater or (for the very brave) the International Cryptozoology Museum, or catching a Seadogs minor league baseball game. But Maine’s best highlights for children are the sea and the sand. And for that, families should consider staying outside the city proper. The Casco Bay Islands offer opportunities to enjoy the great outdoors by cycling, sea kayaking, and swimming, not to mention the thrill of commuting by ferry. Alternatively, Cape Elizabeth is home to two fantastic state parks with expansive beaches, walking trails, an old fort, and a lighthouse. Bonus: The old-fashioned amusement park Palace Playland, in Old Orchard Beach, is just a half-hour drive further south.
  • Best Neighborhood in Portland for Shopping: Downtown, Old Port
    Shopping means different things to different people, but Portland (and environs) has something for everyone. In South Portland, ambitious shoppers will find the state’s largest shopping center, the Maine Mall, with more than 140 stores under one roof. About 17 miles north of Portland, the town of Freeport is famous for its dozens of outlets, appealing to bargain hunters. But the best Portland souvenirs – local foodstuffs, artworks, handicrafts, and other unique items – are right here in the Old Port. Look no further for a clever tote bag made from recycled sails. Nearby, the streets of Downtown house more functional but equally interesting shopping, such as art galleries, bookstores, and funky fashion houses. Nobody, but nobody, leaves empty-handed from the three-story second-hand mecca, Portland Flea-For-All.
  • Best Neighborhood in Portland Without a Car (for walking): Casco Bay Islands, Old Port
    Visitors who are in Portland without a car would do well to stay in the Old Port, a compact neighborhood where scores of restaurants and shops are packed into a few blocks. The surrounding neighborhoods of Downtown, the West End, and the East End are also within walking distance. Another appealing option is to stay on one of the Casco Bay islands, which are accessible by ferry from the mainland. No car is needed on the islands, as the best way to get around is by bicycle. When coming into the city, the ferry drops travelers on the edge of the Old Port district to explore on foot.

The 6 Best Neighborhoods in Portland for Tourists

1. Old Port

The Old Port of Portland, Maine
Portland’s history as a working fishing port is alive and well in vibrant Old Port, where the cries of seagulls and the smell of fish waft in on sea breezes. The working port district is still dominated by boat docks and fishing wharves. But nowadays, the fishing boats share space with commuter ferries and tour boats (including some lobster boats that welcome tourists aboard). Seafood restaurants nestle in beside the waterfront warehouses. Away from the docks, the historic redbrick buildings now house lobster shacks, coffee shops, cozy pubs, and unique boutiques, as well as a few excellent places to stay.

2. Downtown/Arts District

Twilight city view of Downtown Portland, Maine
Downtown Portland is only a few blocks inland from the Old Port, yet its atmosphere is notably more modern and more functional. This is Portland’s workaday world with office buildings and busy commuters. It is also home to the bulk of Portland’s museums and hotels, which makes it an excellent choice as a place to stay. Downtown Portland is sometimes called the “Arts District”, as it contains the excellent Portland Museum of Art, the Maine College of Art, and more than a few prominent theaters, galleries, and maker-spaces, Maine Craft being a favorite.

3. West End

View of Portland, Maine's West End
The West End is a gracious residential area, its tree-lined streets studded with elegant Victorian mansions. Some of these homes now operate as B&Bs and boutique hotels, offering an intimate and artistic experience for Portland visitors. At the far end of the neighborhood, the Western Promenade is a delightful, meandering park with lovely views of the Fore River and beyond. The West End is short on traditional tourist attractions, but it’s only about one mile to the Old Port and Downtown museums and sights.

4. East End (Munjoy Hill)

Portland City Skyline from Portland Observatory on Munjoy Hill
The eastern end of the Portland peninsula centers on Munjoy Hill, crowned with the Portland Observatory. The East End was always a rough-around-the-edges working-class neighborhood, populated by immigrants and dockworkers (and plagued by crime in the second half of the 20th century). Like many edgy urban areas across the country, the East End has experienced a rebirth in recent decades, spurred by artists, activists, and young urban professionals. Nowadays, residents and visitors to the East End enjoy trendy restaurants and craft breweries, a few eclectic museums, and fantastic bay views from the Eastern Promenade, not to mention some of the city’s most affordable places to stay.

5. Casco Bay Islands

Great Diamond Island in Casco Bay near Portland, Maine
Three miles off the coast of Portland, Peaks Island is a charming residential island with an appealing atmosphere of a summer resort. Attractions here include pedaling the 4-mile Peaks Island Loop, swimming at Sandy Beach, and cooling off with a treat from Down Front Ice Cream. Downtown Portland is an 18-minute ferry ride away. Other nearby island options with fancier digs include Chebeague Island and Great Diamond Island.

6. Cape Elizabeth

Portland Head Lighthouse in Cape Elizabeth near Portland, Maine
About eight miles south of Portland, Cape Elizabeth is a picturesque residential area facing the sea. The Portland suburb is populated with attractive homes on shady streets, offering a quiet option for travelers who do not prefer the city. Along the coast, state parks, hidden coves, and secluded beaches punctuate the rocky bluffs. Here, the landmark Portland Head Light beacons to passing travelers on land and on sea, while a few appealing beach resorts offer fabulous sea views and chilly waters.

About Santorini Dave

Santorini Dave Santorini Dave was started in 2011 by a guy who loves Greece and Europe, travel and great hotels. We're now a small team of writers and researchers dedicated to providing the best travel content on the internet. We focus on Santorini, Mykonos, Athens, and Greece, offering recommendations for top hotels, neighborhoods, and family-friendly hotels worldwide. Dave can be contacted at dave@santorinidave.com.