Historic Hotels & Inns in Portland, Maine

The neighborhoods

Where to stay, by area

Old Port & waterfront

Portland’s historic commercial waterfront, much of it rebuilt in brick after the 1866 fire, runs down cobblestone streets to fishing boats, water taxis and the Casco Bay Lines ferry terminal on the Maine State Pier. Two verified stays are here, both inside the Portland Waterfront historic district: The Press Hotel, in the 1923 Gannett Building that housed the Portland Press Herald, and the Portland Regency, in Frederick A. Tompson’s 1895 State of Maine Armory, a hotel since 1987. It is the liveliest part of the peninsula, and since July 1, 2026 its meters are the city’s priciest, at $3 an hour.

Arts District & Congress Street

Congress Street is Portland’s main street and the spine of the Arts District, with the Portland Museum of Art, galleries and Monument Square; the City Council made much of its inner stretch a historic district in 2009. The Westin Portland Harborview, at Congress Square, opened in 1927 as The Eastland and reopened as a Westin in December 2013 after its interior was gutted. METRO’s downtown hub, METRO Pulse, is a block off Congress.

West End & Western Promenade

The quiet residential side of the peninsula, which Visit Portland calls one of the best-preserved Victorian neighborhoods in the country. The Western Promenade Historic District holds 420 buildings from 1850 to 1920 and ends at the Western Promenade, a park on a wooded bluff landscaped by the Olmsted Brothers. Four verified stays are here: the West End Collection (an 1870 brick row house on Pine Street and the 1884 former Pomegranate Inn on Neal Street), The Chadwick (the 1891 George H. Morey House), The Francis (Fassett’s 1881 Mellen E. Bolster House on Congress Street) and Blind Tiger, in an 1823 house on Danforth Street at the West End’s eastern edge. The Francis puts the Old Port a 15 to 20 minute walk away.

Casco Bay islands

Diamond Cove, on Great Diamond Island about a mile off Portland, is a car-free private community built into Fort McKinley, a harbor-defense fort whose brick barracks and officers’ quarters ring a parade ground; the Fort McKinley Historic District was listed on the National Register in 1985. The Inn at Diamond Cove, in a former Army barracks, opened on July 17, 2015 and meets guests at the dock with golf carts or a van. Casco Bay Lines sails there from 56 Commercial Street in 30 to 45 minutes; visitors may walk Diamond Avenue to the restaurants but not the private grounds or beaches without an escort.

Before you book

Planning your stay

Getting around

Portland International Jetport is about 4 miles from downtown, linked by METRO Route 7 and taxis. Amtrak’s Downeaster stops five times a day each way at the Portland Transportation Center, about 2.5 miles from downtown, and METRO Route 1 runs from there to the Arts District and the Old Port. The peninsula is walkable, with most points within a 1 to 2 mile walk; METRO buses cost $2 cash, Route 8 loops the peninsula past the ferry terminal, and Casco Bay Lines’ year-round ferries leave the Maine State Pier for the islands.

Parking

Since July 1, 2026, most Portland meters cost $2.50 an hour and Old Port meters $3, paid from 9 a.m. to 7 p.m. Monday to Saturday and free on Sundays and holidays; most allow two hours. Overnight, use a garage: Visit Portland’s September 2026 list has Custom House Square (25 Pearl St.) and the Casco Bay Garage by the ferry terminal at $5 an hour, $40 maximum, and Casco Bay Lines says its garage often fills in summer. The Francis (for direct bookings) and The Chadwick include off-street parking, Blind Tiger has limited spaces at $25 a night, the Westin sends guests to the 181 High Street garage ($38 a day in January 2026), and Diamond Cove guests leave the car in Portland.

When to go

Summer is peak: Casco Bay Lines ran its fullest timetable from June 20 to September 7 in 2026, Diamond’s Edge on Great Diamond Island opens late May to late September, and the Inn at Diamond Cove meets every ferry with golf carts from Memorial Day through Labor Day weekend. Fall brings foliage, and from October 13, 2026 to April 16, 2027 the island ferry’s round-trip fare drops to $8 from $16. In winter the draw is food: Maine Restaurant Week ran March 1 to 12 in 2026, and its 2027 dates weren’t published when we checked.

Accessibility

Visit Portland warns of cobblestones and narrow paths in the Old Port, and the West End climbs to the Western Promenade’s bluff; cars with disability plates or placards park free at meters for twice the posted limit. The Francis has an elevator to all floors and a room with a roll-in shower, and the Inn at Diamond Cove lists a level or ramp entrance and accessible routes to its accessible rooms. The Chadwick and Blind Tiger have no elevator and aren’t wheelchair accessible. Casco Bay Lines offers assisted boarding, but the gangway’s slope changes with the tide.

Before you book

Book The Francis direct to get its off-street parking. The Chadwick and the West End Collection both want 14 days’ notice to cancel and take two guests per room; the West End Collection requires bookers to be 25 or older, and The Chadwick takes children only over 14. At Diamond Cove, budget the $35 daily resort fee plus the ferry, cancel at least 14 days out, and reserve Fogg’s Water Taxi early if you’d rather skip the ferry.