Historic Hotel Portland: Compare Oldest, Luxury & Downtown

Portland’s historic hotels are not just places to sleep — they are living archives of the city’s architectural and cultural evolution. This guide compares five of the most acclaimed downtown heritage properties, drawing on official property histories, verified opening dates, and published guest sentiment to help you decide where to book. Across both Oregon and Maine, these hotels offer distinct experiences for couples, history enthusiasts, luxury seekers, and wedding planners.

Last checked: 2026-08-09

Heathman Hotel: Oldest operating historic hotel in Portland, Oregon; opened 1927; location 1001 SW Broadway · Sentinel Hotel: Historic downtown luxury hotel in Portland, Oregon; restored early 20th-century building · The Benson Portland: Curio Collection by Hilton; ranked #1 heritage hotel on TripAdvisor Portland list · Portland Regency Hotel & Spa: Historic hotel option in Portland, Maine; featured on Expedia’s historic hotel guide

What is the oldest hotel in Portland?

The answer depends on which Portland you mean — Oregon or Maine — and on how you define “oldest.” In Portland, Oregon, the Heathman Hotel (opened 1927, 1001 SW Broadway) markets itself as the oldest continuously operating hotel in downtown Portland, emphasizing a nearly century-old history on its official site (Heathman Hotel history page). However, several other properties contain older building fabric. The Sentinel Hotel‘s east wing was originally the Seward Hotel, completed in 1909, making it the oldest standing hotel building in downtown Portland (Montecristo Magazine). The Seward building was renamed the Governor Hotel in 1931 and closed in the mid-1980s before reopening in 1992 as part of the Sentinel complex (Wikipedia — Seward Hotel).

The Benson Hotel opened on March 5, 1913, built by lumber tycoon Simon Benson as an annex to the adjacent Oregon Hotel (Oregon Encyclopedia). It has operated continuously as a luxury hotel under a single identity ever since. The Hotel deLuxe (originally Hotel Mallory) opened in 1912, commissioned by lawyer and politician Rufus Mallory (Hotel deLuxe official history). In Portland, Maine, the Portland Regency Hotel & Spa is a verified historic property listed among dozens of options on Expedia.

Heathman Hotel: Portland’s oldest continuously operating historic hotel

The Heathman’s official history highlights its role as a cultural hub, with proximity to Portland’s performing arts venues and a long-standing association with writers and artists. It opened in 1927 at 1001 SW Broadway and has remained in operation since, making it the oldest downtown hotel that has never closed or rebranded.

Portland Hotel (1890–1951): the city’s first grand hotel

The Portland Hotel predates all current properties. It opened in 1890 and operated for 61 years before closing in 1951 (The Oregonian). While no longer standing, its legacy anchors Portland’s historic hotel narrative.

Best historic hotels in Portland, Maine

This article covers both Portland, Oregon and Portland, Maine — they are separate cities. In Portland, Maine, the historic hotel scene is distinct and plentiful. Over 98 historic hotels are listed on Expedia for Portland, Maine alone (Expedia historic hotel guide).

Portland Regency Hotel & Spa

The Portland Regency Hotel & Spa is a verified historic option in downtown Portland, Maine. It occupies a 19th-century building in the Old Port district and is frequently cited on travel platforms as a top heritage property.

Hampton Inn Portland Downtown – Waterfront

While not a historic building itself, this hotel sits within Portland, Maine’s historic waterfront district and offers easy access to the city’s 19th-century architecture and cobblestone streets.

Historic hotel options on Expedia (98+ listings)

Expedia’s curated guide to historic hotels in Portland, Maine includes more than 80 options, from boutique inns to larger properties, reflecting the city’s deep maritime heritage and well-preserved 19th-century building stock.

What are some historic hotels in downtown Portland?

Portland, Oregon’s downtown core holds a dense cluster of historic hotels, each with distinct architecture and provenance. Here are the three most prominent.

Sentinel Hotel – West End luxury

The Sentinel occupies two National Register-listed buildings at 614 SW 11th Avenue in the West End. The east building (Seward Hotel, 1909) features Early Modern and modified Arts and Crafts styling with glazed terra cotta — a novel material in Oregon at the time (Montecristo Magazine). The west building (1923 Elks Temple) was originally the Portland Elks Lodge No. 142. Both buildings were individually listed on the National Register: the Elks Temple in 1978 and the Seward in 1985 (Wikipedia — Sentinel Hotel).

Heathman Hotel – Broadway landmark

At 1001 SW Broadway, the Heathman has operated since 1927 and is known for its literary and arts connections. Its official history describes it as a “cultural hub” with proximity to the Arlene Schnitzer Concert Hall and Portland’s performing arts venues.

The Benson Portland – Curio Collection by Hilton

At 309 SW Broadway, the Benson (opened 1913) was designed in the French Renaissance style by the Portland firm Doyle, Patterson & Beach (Oregon Encyclopedia). Its opening was promoted as providing first-class accommodations, and it quickly gained a reputation as one of Portland’s most opulent hotels (Portland Monthly). Today it operates as part of Hilton’s Curio Collection.

What is the best historic hotel in Portland, Oregon?

The answer depends on your priorities — history, location, or luxury. Here is how the top contenders compare.

What hotel is in Portland from 50 Shades of Grey?

The Heathman Hotel in Portland, Oregon, was used as a filming location for the 50 Shades of Grey film series. The hotel’s official materials highlight this cultural connection, and it is one of the most frequently searched historic-hotel associations in Portland by pop-culture fans (Heathman Hotel history). The Heathman’s interior spaces, particularly its lobby and restaurant areas, doubled for scenes set in the fictional accommodations of the film’s characters.

Best historic hotels by traveler type

For couples

The Heathman Hotel and Hotel deLuxe both offer intimate settings with distinctive design. Hotel deLuxe’s Driftwood Room bar, added in the 1950s, is one of Portland’s best-known midcentury-style hotel bars and a popular evening spot for couples (Vancouverscape).

For history enthusiasts

The Sentinel Hotel offers the deepest architectural history, with two individually NRHP-listed buildings spanning 1909 to 1923. Hotel deLuxe (NRHP-listed in 2006 as Hotel Mallory) provides a well-documented lineage back to 1912, including notable guests like Bob Hope, Goldie Hawn, Kurt Russell, and James Beard (Vancouverscape).

For luxury travelers

The Benson Portland — Curio Collection by Hilton, with its French Renaissance design, 100-year continuous operation, and #1 TripAdvisor ranking among heritage hotels, is the top pick for those prioritizing luxury and service consistency.

For wedding planners

Several historic Portland hotels cater to wedding events. The Heathman and Benson offer dedicated event spaces and historic ballrooms. In Portland, Maine, the Portland Regency Hotel & Spa is a popular venue for intimate weddings in the Old Port district.

Pricing bands and location context

All prices below are qualitative estimates drawn from published rate ranges on booking platforms and hotel websites. Actual rates vary by season.

• $$$ (Premium, $250–$450/night): Heathman Hotel, Benson Portland, Sentinel Hotel — downtown locations, full-service amenities, heritage premium.
• $$ (Moderate, $150–$300/night): Hotel deLuxe, Embassy Suites by Hilton Portland Downtown — more accessible pricing while retaining historic character.

For Portland, Maine, historic hotel rates on Expedia range from approximately $120–$350 per night depending on season and property category.

Location and getting there

Portland, Oregon’s historic hotels are concentrated in the downtown core, within walking distance of Powell’s City of Books, the Portland Art Museum, and the Arlene Schnitzer Concert Hall. The Heathman (1001 SW Broadway) and Benson (309 SW Broadway) sit on Broadway itself, while the Sentinel (614 SW 11th Avenue) is one block west. Hotel deLuxe (729 SW 15th Avenue) is on the western edge of downtown near Washington Park. MAX Light Rail serves all locations via the red, blue, green, and yellow lines at Pioneer Square and 10th/11th Avenue stations. Portland International Airport (PDX) is a 20-minute MAX ride to downtown.

Portland, Maine’s historic hotels cluster in the Old Port district and along the waterfront, within walking distance of the Portland Head Light, Old Port boutiques, and the Maine waterfront.

Frequently asked questions

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