Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Old Port's cobblestone streets and 19th-century brick buildings transport you back in time while keeping you firmly in Portland's lively present. The waterfront promenade serves up perfect views of fishing boats bobbing in Casco Bay alongside plenty of spots to grab a craft beer. Art lovers can hop between galleries like Fore Street and Salt Gallery before catching live music at local venues. Fresh seafood dominates the restaurant scene with lobster rolls that will make your taste buds dance. The area is incredibly walkable with ferry services taking you to nearby islands when you want to explore beyond the mainland. Boutique hotels in historic buildings offer cosy places to crash after a day of shopping and harbour gazing.
City centre Portland enchants with historic cobblestone streets and a lively waterfront where lobster boats bob alongside ferry terminals. Art lovers can explore local galleries and the Portland Museum of Art, while foodies dive into fresh seafood and craft beer scenes. The charming brick buildings house boutique shops perfect for finding unique Maine-made treasures. Getting around is easy on foot with most attractions packed into a walkable core. Cosy boutique hotels occupy converted Victorian buildings, offering harbour views and local character. When night falls, live music spills from taverns while the salty harbour breeze carries the promise of tomorrow's adventures.
Portland's East End combines coastal charm with area character along its stunning 2.1-mile Eastern Promenade trail. Panoramic views of Casco Bay's islands and lighthouses await as you stroll past locals enjoying picnics on grassy slopes. The historic Portland Observatory and Abyssinian Meeting House offer glimpses into the past, while tree-lined streets showcase Victorian homes. Artisanal coffee shops and craft breweries nestle between authentic area spots, perfect for refuelling after waterfront walks. Most accommodation is boutique B&Bs in converted historic homes with personalised service. The area's excellent walkability and METRO bus connections make exploring easy, whether you're heading to East End Beach or venturing city centre.
West End
Portland's West End offers a glimpse into architectural heritage with its stunning Victorian and Colonial Revival mansions lining tree-canopied streets. The Western Promenade stands as the crown jewel, treating visitors to panoramic views of Casco Bay through towering elms. History buffs will love exploring the Victoria Mansion and Portland Fire Museum while soaking in the neighborhood's peaceful, residential charm. Intimate bistros and upscale farm-to-table restaurants showcase locally-sourced Maine ingredients throughout the area. Historic bed & breakfasts in converted Victorian mansions provide personalised service with period charm. City centre Portland is just a 15-minute walk away, with METRO bus routes connecting the area to the rest of the city.
East Bayside
East Bayside's industrial buildings have transformed into a buzzing creative playground filled with craft breweries, distilleries, and coffee roasters. Colourful murals splash across brick facades while artisans work in converted warehouses. The area offers authentic cultural experiences, from Somali sambusas to craft beer flights, with the Maine Jewish Museum and historic Abyssinian Meeting House adding cultural depth. Just a 10-minute walk from city centre Portland, this walkable area is well-connected by METRO buses and offers bike-friendly routes. Boutique inns and holiday rentals in converted industrial spaces provide character-filled stays, while the Eastern Waterfront Trail offers harbour views and a refreshing break from the artsy urban landscape.
If you want to see a show while you're in town, try and grab some tickets at State Theatre in Downtown Portland. Why not take a stroll along the port and watch the sunset while you're here? If you enjoy the show and want to see another, Portland Stage, Center for Cultural Exchange, and Port City Music Hall are all a short walk away.
You can spend time browsing the exhibits at Portland Museum of Art during your travels in Portland. Stroll along the area's waterfront or experience its great live music.
Eastern Promenade is just one of the places to see in Portland, so why not enjoy the other things to explore during your travels? Amble around the area's waterfront or attend a sporting event.
You can find out about the history of Portland with a stop at Portland Observatory. Stroll along the area's waterfront or experience its acclaimed theatre scene.
Wander cobblestone streets lined with 19th-century brick buildings, leading to a bustling working waterfront. Sample fresh lobster rolls at waterside eateries before exploring lighthouses or embarking on a scenic harbour cruise.
Visitors really like Portland, especially its live music, port and restaurants. Why not spend time at Bayside Bowl and Portland Observatory?While you're in town, don't miss a chance to see sights like Merrill Auditorium and Fore Street Gallery.
