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Portland Holidays

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Where to stay in Portland

Find the best Portland areas for the activities you enjoy most.
A marina with boats docked, a wooden pier, and a red brick building with balconies.

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.

A building with a large arched window and a sign that reads "STATE".

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.

A calm lake with several kayaks lined up on the shore and boats in the water.

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.

A historic building with ornate architecture, large windows, and a prominent tower.

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.

A historic building with a sign reading "Portland Museum of Art McLellan House."

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

A multi-story brick building with a large arched window and a sign that reads "STATE".

State Theatre

8.8/10 (392 reviews)
This historic 1929 venue showcases national touring acts in an intimate 1,200-seat setting. Experience hand-wrought architectural details while enjoying performances ranging from rock concerts to comedy shows.

What to do in Portland

Portland Lighthouse Boat Cruise with Oysters & Prosecco

Portland Explorer: Boat Cruise with Oysters & Prosecco

S$177
per adult
0% of travellers recommend
Portland Explorer: Boat Cruise with Oysters & Prosecco
See all activities in Portland

Portland Hotel Deals

Lobby

Comfort Inn South Portland Airport

Comfort Inn South Portland Airport
2.5 star property
6.6 km from Portland
8.6 out of 10, Excellent, (2,288 reviews)
"Has airport shuttles from 3:30 am."
The price is S$207
includes taxes & fees
1 Sept - 2 Sept
Comfort Inn South Portland Airport
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.
See all properties in Portland

Frequently 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.

Book with confidence

Things to do in and around Portland

Portland, Maine, offers a delightful mix of outdoor activities and family-friendly attractions. Visitors can enjoy a range of exciting excursions, including sightseeing tours and sea combo adventures. The city is also home to vibrant arena entertainment, theatres, and live music concerts, making it a perfect destination for those seeking both relaxation and entertainment. Explore various tour packages to make the most of your vacation in this charming coastal city.

Shopping

The nearest shopping destination is Maine Mall, located 6.4km from Portland, offering a vibrant mix of shops and entertainment. If you're up for a drive, consider visiting the LL Bean Flagship Store, 25.7km away, or The Willows Flea Market, 48.3km away, for unique finds.

Recreation

Experience the vibrant atmosphere at Thompson's Point with live music, enjoy the thrill of sports at Fitzpatrick Stadium, or immerse yourself in the cultural charm of the State Theatre, where romance and entertainment intertwine, creating the perfect setting for relaxation and enjoyment in Portland.

Adventure

Bayside Bowl is a vibrant arcadeAdventureZone in Portland, offering a lively atmosphere for family fun and thrilling games. For fitness enthusiasts, the Racket & Fitness Center provides an exhilarating adventureActivity, while the MAGAN Trailhead, located 11.3km from Portland, invites you to explore stunning outdoor scenery on its hikingTrail.

Nightlife

In Portland, Maine, enjoy a vibrant nightlife featuring the Old Port district, known for its lively bars and seafood restaurants. Visit the Arts District for craft breweries and live music venues, or explore the waterfront for stunning views and casual pubs, creating an unforgettable evening atmosphere.

Find the best attractions in Portland

Portland, Maine, is an ideal destination for outdoor enthusiasts and families, offering a mix of scenic beauty and cultural experiences. Explore popular attractions such as historic houses, vibrant beaches, and the Portland Museum. These points of interest provide a delightful blend of culture, family fun, and outdoor adventures, making your visit truly memorable.

  • Charles Q. Clapp House: A picturesque historic house, the Charles Q. Clapp House offers a glimpse into Portland's rich cultural heritage. Its charming architecture and well-preserved interiors reflect the elegance of a bygone era, making it a delightful stop for history enthusiasts and those seeking to soak in local culture.
  • Cross Insurance Arena: This vibrant arena is the heart of entertainment in Portland, hosting a variety of events from concerts to sporting matches. With a lively atmosphere perfect for families, it promises an exhilarating experience, bringing together locals and visitors for unforgettable moments.
  • University of New England: A modern college university, the University of New England boasts a beautiful campus that embodies the urban spirit of Portland. Visitors can explore its educational facilities and enjoy the scenic surroundings, making it a great spot for a leisurely stroll.

Best time to go to Portland

The best time to visit Portland can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Portland falls in July, when visitor numbers are moderately high and weather is mostly sunny with light rain. The coolest average temperature in Portland falls in January, visitor numbers are moderately low and weather is mostly sunny with light rain.

Tips to save on your trip to Portland

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling during the off-peak season (typically January to March) for more affordable package holidays to Portland.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.