Portland Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to €900 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

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.

Things to do in and around Portland

Portland, Maine, is an ideal destination for outdoor enthusiasts and families alike, offering a variety of activities such as arena entertainment, theatre performances, and music concerts. Visitors can explore exciting excursions, tour packages, and sightseeing options, including enticing sea combo tours that showcase the region's stunning coastal scenery. Whether you're seeking adventure or relaxation, Portland has something for everyone.

Shopping

In Portland, the Maine Mall offers a vibrant mix of shops and entertainment, just 6.4km away. If you're up for a drive, the LL Bean Flagship Store is 25.7km away, showcasing outdoor gear and apparel. For a unique experience, The Willows Flea Market is located 48.3km from the city.

Recreation

Experience the vibrant atmosphere at Thompson's Point, where live music resonates. Enjoy a romantic evening at the State Theatre, perfect for families and cultural enthusiasts. For sports lovers, Hadlock Field offers an exciting stadium experience, making it a thrilling destination for all.

Adventure

Bayside Bowl provides a vibrant atmosphere for bowling and arcade games, perfect for families seeking adventure. The Racket & Fitness Center offers a range of exhilarating activities for fitness enthusiasts. For nature lovers, MAGAN Trailhead is a scenic hiking trail located 11.3km from Portland, showcasing the area's breathtaking outdoor beauty.

Nightlife

Portland’s nightlife buzzes with vibrant bars and live music venues. Visit the Thirsty Pig for local craft beers and delicious sausages. For a unique cocktail experience, check out the speakeasy-style bar, The Jewel Box, where creative concoctions await. Enjoy the lively atmosphere and friendly locals.

*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 perfect for outdoor and family vacations, offering a blend of scenic beauty and cultural experiences. Explore popular attractions like historic houses, vibrant entertainment venues, and picturesque beaches. Don't miss a visit to the Portland Museum for an enriching experience. With something for everyone, Portland promises a delightful getaway filled with adventure and relaxation.

  • Portland Museum of Art: Discover a vibrant collection of American, European, and contemporary art in this cultural gem. The museum features rotating exhibitions and offers a glimpse into the artistic heritage of the region, making it a perfect stop for art enthusiasts.
  • East End Beach: Relax on the sandy shores of East End Beach, where you can soak up the sun, enjoy stunning views of Casco Bay, or partake in beach activities. This local favourite offers a laid-back atmosphere ideal for picnics and leisurely strolls along the coast.
  • Wadsworth-Longfellow House: Step back in time at the historic home of poet Henry Wadsworth Longfellow. This beautifully preserved house highlights the life and work of one of America's literary icons while offering insight into early 19th-century life in Portland.

Best time to go to Portland

The best time to visit Portland is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are moderately high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, 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 to Portland during the low season (January to March) for more affordable options.
  • 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
Fully refundable
€112
1 Sept - 2 Sept
includes taxes & fees
8/10 Very good! (1,643 reviews)
"Pest control was out several times during our stay. Not to sure the reason. I k ow that pets are allowed. So maybe an issue with something."

Reviewed on 24 Aug 2026

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
€114
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very good! (1,066 reviews)
"If you were there for a couple days you could take advantage of the fitness area, sauna, hot tub, or two heated pools. It was clean and close to the airport. Honestly, the only issue was that it was so dated."

Reviewed on 25 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
€241
30 Aug - 31 Aug
includes taxes & fees
9.4/10 Exceptional! (1,757 reviews)
"The staff was really lovely and helpful. A lovely, very well located historic property. The spa was very nice!"

Reviewed on 25 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
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
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 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

€67
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

€118
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.