Portland Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to AU$2,500 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Your Portland Holiday

When a fun city break is calling, answer it with a holiday package to Portland. The neighbourhood of Parkside, which is good for festivals, markets and walking, makes a great base for your adventures. Want to venture out and explore? Portland Head Light, Portland Museum of Art and University of Southern Maine are just a few of the top places to visit during your trip to Portland. Don't put off exploring this destination any longer. The ultimate Portland holiday is just a few clicks away with Expedia.

Our guide on 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.

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.

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.

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.

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.

Portland Holiday

Things to do in and around Portland

Portland, Maine, is ideal for outdoor enthusiasts and families seeking scenic adventures. The city boasts a variety of activities, including arena entertainment, theatres, and music concerts. Key attractions include sightseeing tours, cycling trails, and museums, where visitors can purchase tickets for an enriching experience. Whether you're wandering through picturesque landscapes or enjoying vibrant cultural offerings, Portland promises a memorable escape.

Shopping

In Portland, you can visit The Cheese Iron for delightful gourmet treats, located 9.7km away. The Maine Mall, just 6.4km from the city, offers a fantastic mix of shopping and entertainment. If you're up for a drive, The Willows Flea Market, situated 48.3km away, showcases vibrant local goods.

Recreation

Thompson's Point offers a vibrant atmosphere with live music, perfect for relaxation and enjoyment. The State Theatre provides a romantic and cultural experience through captivating performances, while Hadlock Field brings the excitement of sports, making it ideal for an energetic outing in Portland.

Adventure

At Bayside Bowl, experience a lively atmosphere with bowling and arcade games, perfect for family fun. The Racket & Fitness Center offers a range of adventurous activities to keep you active. For a scenic outdoor experience, hike the MAGAN Trailhead, located 11.3km from Portland, surrounded by beautiful nature.

Nightlife

Portland's nightlife is vibrant with a mix of craft breweries and cosy bars. Visit The Blueberry for inventive cocktails and enjoy live jazz at The Chocolate Bar. For a laid-back vibe, the Portland House of Music offers great local performances, perfect for a memorable evening.

*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 blend of scenic beauty and cultural experiences. Visitors can explore various attractions, including entertainment arenas, historic houses, and beautiful beaches. Notable points of interest include the Portland '5 Centers, Portland Centre, Portland Roses, and other local attractions that cater to diverse interests, ensuring a memorable holiday for every traveller.

  • University of Southern Maine: This historic college offers a vibrant cultural atmosphere, with beautiful architecture and a lovely campus. Explore its galleries and attend local events that showcase the artistic talents of students and faculty alike.
  • East End Beach: Enjoy the stunning coastal views and sandy shores at East End Beach, a perfect spot for relaxation and sunbathing. The gentle waves and vibrant beach vibes make it an ideal location for a leisurely day by the sea.
  • Victoria Mansion: Step back in time at this exquisite historic house, renowned for its stunning architecture and opulent interiors. Guided tours reveal the rich history and artistic details that make Victoria Mansion a true gem of Portland.

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

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Portland.
  • 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.

Portland Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Portland Intl. Jetport Airport (PWM)
Population
66,900
Max Temp Winter
-1.11ºC
Max Temp Summer
24ºC
Top Sights
State Theatre, Higgins Beach and Portland Museum of Art

Our pick of the best Portland Hotel Deals

Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

1230 Congress St Portland ME
Fully refundable
AU$182
7 Sept - 8 Sept
includes taxes & fees
Clarion Hotel Portland Airport ME
Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

81 Riverside St Portland ME
Fully refundableReserve now, pay when you stay
AU$172
31 Aug - 1 Sept
includes taxes & fees
8.2/10 Very good! (1,060 reviews)
"Great experience and highly recommend"

Reviewed on 23 Aug 2026

Fireside Inn & Suites Portland
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
AU$361
30 Aug - 31 Aug
includes taxes & fees
9.4/10 Exceptional! (1,752 reviews)
"Great location (near shops, restaurants and bars). The bed was extremely comfortable."

Reviewed on 22 Aug 2026

Portland Regency Hotel & Spa
See all 498 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 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.
See properties
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.
See properties
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.
See properties
A beach with people sunbathing and swimming, boats in the water, and a rocky shoreline.

East End Beach

9.2/10 (90 reviews)
Portland's only public beach offers stunning panoramic views of Casco Bay and its islands along the Eastern Promenade. Enjoy the pebbly shoreline for sunbathing, swimming, or launch a kayak.
See properties

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.
See properties

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.
See properties

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.
See properties

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.
See properties

What to do in Portland

Sunset Windjammer Cruise Along the Coast of Portland Maine

Sunset Windjammer Cruise Along the Coast of Portland Maine

AU$110
per adult
90% of travellers recommend
Sunset Windjammer Cruise Along the Coast of Portland Maine
Portland Lighthouse Boat Cruise with Oysters & Prosecco

Portland Explorer: Boat Cruise with Oysters & Prosecco

AU$196
per adult
Portland Explorer: Boat Cruise with Oysters & Prosecco
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.