Portland Holidays
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Our guide on where to stay in Portland
Old Port
Old Port captures Portland's maritime soul with cobblestone streets and 19th-century brick buildings lining the scenic harbour. Fishing boats bob alongside pleasure craft while local artisans display their wares in converted warehouses. History enthusiasts can explore the weathered piers and Victorian-era facades that tell stories of Maine's seafaring past. The area buzzes with activity from morning to night. Award-winning seafood restaurants serve fresh-caught lobster while craft breweries pour local favourites in historic buildings. Art galleries showcase coastal-inspired works, and boutique shops offer Maine-made treasures within easy walking distance of the bustling waterfront promenade.
Downtown Portland
City centre Portland combines New England charm with a lively waterfront scene. Cobblestone streets wind past brick buildings housing artisan galleries, craft breweries, and seafood restaurants along Casco Bay. The historic district buzzes with local culture and maritime heritage. Explore museums like the Portland Museum of Art or catch performances at Merrill Auditorium. The working harbour offers scenic walks and ferry trips to nearby islands. With its walkable layout, vibrant dining scene, and shopping boutiques, this area perfectly captures Maine's coastal spirit.
East End
Portland's East End offers a picturesque coastal escape with its stunning 2.1-mile Eastern Promenade trail. Panoramic views of Casco Bay and offshore islands create the perfect backdrop for morning walks or sunset picnics. Victorian and Colonial Revival homes line tree-shaded streets that blend historic charm with modern flair. This quiet residential haven has evolved into a creative hub with artisanal coffee shops and craft breweries. Visitors can explore the Portland Observatory or relax at East End Beach. The area maintains its authentic local vibe while welcoming travellers seeking a genuine Portland experience.
West End
Portland's West End showcases grand Victorian mansions and tree-lined streets that feel worlds away from downtown's bustle. Stroll along the Western Promenade for stunning views of Casco Bay through towering elms. This prestigious area offers glimpses into Portland's 19th-century maritime wealth through its architectural treasures. Visitors can explore Victoria Mansion and the Portland Fire Museum within this refined residential haven. Local cafes and boutique shops provide authentic Portland experiences without the tourist crowds. City centre attractions remain just a peaceful 15-minute walk away through streets rich with historical character.
Portland Arts District
The ample dining options and captivating waterfront views are top of the list for many visitors to Portland Arts District. A stop by Cross Insurance Arena or Portland Museum of Art might round out your trip.
Discover the most popular places to visit in Portland
What to do in Portland
Casco Bay Morning Windjammer Sail
Portland Explorer: Boat Cruise with Oysters & Prosecco
Sunset Windjammer Cruise Along the Coast of Portland Maine
Portland Hotel Deals
Comfort Inn South Portland Airport
Comfort Inn South Portland Airport
La Quinta Inn & Suites by Wyndham Portland DT/Maine Med
La Quinta Inn & Suites by Wyndham Portland DT/Maine Med
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel
Spark by Hilton Portland Airport Maine Mall
Spark by Hilton Portland Airport Maine Mall
Holiday Inn Express Hotel & Suites South Portland by IHG
Holiday Inn Express Hotel & Suites South Portland by IHG
Courtyard by Marriott Portland Airport
Courtyard by Marriott Portland Airport
Tru by Hilton Portland Airport Area
Tru by Hilton Portland Airport AreaFrequently Asked Questions
How much does a Portland holiday package cost?
You'll find cheap prices on Expedia for your Portland break. However, factors like your choice of hotel, the season and length of stay will determine how much your holiday to Portland costs.
What are the cheapest months to go to Portland?
You're likely to find lower rates and greater availability in January, February and March. Explore our cheap Portland holiday packages and you could score some great off-season discounts.
How many days is enough for Portland?
We recommend booking a Portland holiday for at least 2 days. This will allow you plenty of time to tick off top sights including East End Beach and Sand Beach, as well as explore neighbourhoods like Downtown Portland and Old Port. You might even be able to make time for a day trip (or two) outside of Portland.
Is it worth booking a holiday package to Portland?
During your Portland holiday, you can count on experiencing some top-notch walking trails and culture. Leave enough time in your itinerary to discover major sights like Thompson's Point and State Theatre.
How to find the best Portland package deals?
Start your search for a Portland package deal by entering your destination and travel dates under our "Packages" tab. Then select a few filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the ideal Portland package deal right away, simply change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Portland escape off to a flying start.
Is it cheaper to book a Portland holiday as a package?
You can enjoy significant savings on your Portland retreat by booking a personalised holiday package. Check the "Package" heading, then select your destination and travel dates to browse the best airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a holiday package to Portland?
Secure fantastic discounts by booking your flights early with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for an impromptu Portland escape.
How to plan a trip to Portland?
- Pick the ideal time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to travel to Portland.
- Figure out your budget: Ensure you have enough money to cover everything from food and transportation to activities and airfares. Your hotel will likely be the largest expense during your trip to Portland.
- Decide your trip length: Think about how much time you'd like to spend discovering Portland. Plan your itinerary so you can get to all the attractions and activities you're interested in at a comfortable pace.
- Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a customised Portland holiday package.