Portland Holidays

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Where to stay in Portland

Find the best Portland areas and neighborhoods for the activities you enjoy most. Learn more about Portland
A tree-lined pathway leading to a brick building with a sign reading "Mercy Hospital Service Entrance".

Downtown Portland

5 out of top 10 points of interest in this area

A noteworthy feature of Downtown Portland is its captivating waterfront views. While you're in town, be sure to stop and check out Cross Insurance Arena and Merrill Auditorium.

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A marina with boats docked, a wooden pier, and a red brick building with balconies.

Old Port

Explore the cobblestone streets in Portland’s historic district, which combines a wealth of history with a thoroughly modern city experience.

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A lighthouse on a rocky shore with a sailboat in the distance.

West End

If you're spending some time in West End, Victoria Mansion and Portland Fire Museum are top sights worth seeing.

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A large, cream-colored building with white columns and a white picket fence in front.

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.

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A red brick building with Gothic architectural features, including pointed arches and a cross on top.

East Bayside

If you're spending some time in East Bayside, Maine Jewish Museum and Cathedral of the Immaculate Conception are top sights worth seeing.

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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.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January26.1°F (-3.3°C)Light RainMostly SunnyModerately LowSlightly Low
February27.0°F (-2.8°C)Light RainMostly SunnyModerately LowSlightly Low
March33.4°F (0.8°C)Light RainMostly SunnyModerately LowSlightly Low
April43.9°F (6.6°C)Light RainMostly SunnyAverageAverage
May54.0°F (12.2°C)Light RainMostly SunnyAverageAverage
June61.9°F (16.6°C)Light RainMostly SunnyAverageAverage
July68.9°F (20.5°C)Light RainMostly SunnyModerately HighSlightly High
August68.5°F (20.3°C)Light RainMostly SunnyModerately HighSlightly High
September62.2°F (16.8°C)Light RainMostly SunnyModerately HighSlightly High
October52.2°F (11.2°C)Light RainMostly SunnyAverageAverage
November41.2°F (5.1°C)Light RainMostly SunnyAverageAverage
December32.9°F (0.5°C)Light RainMostly SunnyAverageAverage

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.

Top hotels in Portland

Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

1230 Congress St Portland ME
S$166
28 Sept - 29 Sept
includes taxes & fees
Clarion Hotel Portland Airport ME
Portland Harbor Hotel

Portland Harbor Hotel

468 Fore Street Portland ME
S$504
20 Sept - 21 Sept
includes taxes & fees
9.2/10 Wonderful! (1,842 reviews)
"No comfortable air chairs in the room as pictured in their promos. No shuttle setvice to or from airport as listed in hotel info. Good location and nice room."

Reviewed on 16 Sept, 2026

Portland Harbor Hotel
Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

81 Riverside St Portland ME
Fully refundableReserve now, pay when you stay
S$159
13 Oct - 14 Oct
includes taxes & fees
8.2/10 Very good! (1,011 reviews)
"We booked last minute when travelling thru the area. We booked a basic room that was accessible because the only one left with a King Bed that did not have a fireplace. Reception staff very polite and efficient. Room was clean, bed was comfortable. Breakfast in the morning did the trick. Looks recently ..."

Reviewed on 16 Sept, 2026

Fireside Inn & Suites Portland
See all 506 properties in Portland
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.

Stay near popular Portland attractions

A 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.
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An art gallery with various paintings and sculptures.

Portland Museum of Art

9.2/10 (610 reviews)
Maine's premier art institution showcases American masterpieces by Homer and Wyeth alongside European treasures by Monet. Visit Friday evenings for free admission and a more intimate viewing experience.
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A lighthouse on a rocky shoreline with a cloudy sky.

University of Southern Maine

8.2/10 (233 reviews)
USM's Portland Campus blends academic excellence with the vibrant urban culture of Maine's largest city. Explore the modern McGoldrick Centre and Portland Commons before venturing into the nearby arts and culinary scene.
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Cross Insurance Arena

8.6/10 (275 reviews)
This city centre Portland venue hosts everything from electrifying concerts to Maine Mariners hockey games. Enjoy premium seating and modern amenities while experiencing the vibrant energy of Maine's largest indoor arena.
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Thompson's Point

8.8/10 (376 reviews)
This riverside cultural hub transforms seasonally, from summer concerts to winter ice skating on the Fore River. Explore local breweries and distilleries while enjoying Portland's vibrant maker scene.
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Hadlock Field

9.8/10 (6 reviews)
Experience the charm of Hadlock Field, home to the Portland Sea Dogs with its iconic "Maine Monster" wall and centerfield lighthouse. Catch an evening game during summer months for the most vibrant baseball atmosphere.
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Merrill Auditorium

8.8/10 (107 reviews)
This historic venue houses the magnificent Hermann Kotzschmar Memorial Organ, offering exceptional acoustics. Experience the Portland Symphony Orchestra in an intimate setting with 1,900 fellow music lovers.
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Maine Narrow Gauge Railroad

You can spend an afternoon studying the exhibits at Maine Narrow Gauge Railroad in Portland. Experience the area's acclaimed theatre scene and great live music.
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What to do in Portland

Portland: Casco Bay Morning Lighthouse Cruise

Portland: Casco Bay Morning Lighthouse Cruise

S$75
per adult
Portland: Casco Bay Morning Lighthouse Cruise
Sunset Windjammer Cruise Along the Coast of Portland Maine

Sunset Windjammer Cruise Along the Coast of Portland Maine

S$98
per adult
90% of travellers recommend
Sunset Windjammer Cruise Along the Coast of Portland Maine
See all activities 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.