Portland Holidays

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Your Portland Holiday

When a break in the city is calling, answer it with a holiday package to Portland. The neighbourhood of Parkside, which is great for festivals, markets and walking, makes a fantastic base for your adventures. Fill your free time with tours of Portland Head Light, University of Southern Maine and Portland Museum of Art, some of the top attractions you just have to see during your trip to Portland. Don't put off your visit to this destination any longer. Your perfect Portland holiday is just a few clicks away with Expedia.

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

4 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, is an ideal destination for outdoor enthusiasts and families alike, offering a variety of activities. Enjoy arena entertainment, theatre performances, and music concerts. Key experiences include excursions, tour packages, and sightseeing options, as well as delightful sea combo tours that showcase the stunning coastal scenery. Whether you're exploring local attractions or indulging in the vibrant culture, Portland promises a memorable holiday experience.

Shopping

For a delightful shopping experience, visit the Maine Mall, just 6.4km from Portland, offering a variety of shops and entertainment. If you're up for a drive, head to Marden's Surplus and Salvage, 27.4km away, or explore The Willows Flea Market, located 48.3km from the city.

Recreation

Experience the vibrant atmosphere at Thompson's Point with live music events that uplift your spirits. At the State Theatre, immerse yourself in cultural performances perfect for a romantic evening or family outing. For sports enthusiasts, Hadlock Field offers thrilling games that energise and entertain.

Adventure

Bayside Bowl is an exciting arcadeAdventureZone in Portland, perfect for families seeking adventure vibes. The Racket & Fitness Center offers a variety of adventure activities for those looking to stay active. For hiking enthusiasts, the MAGAN Trailhead, located 11.3km from Portland, provides stunning outdoor scenery.

Nightlife

Portland's nightlife offers a vibrant mix of craft breweries and lively bars. Start your evening at the iconic Old Port area, where you can enjoy local ales at the Maine Beer Company or savour cocktails at the speakeasy-style Blyth & Burrows, ensuring a memorable night out.

*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 delightful mix of scenic beaches, historic houses, and entertainment arenas. Visitors can immerse themselves in the local culture and enjoy a variety of attractions, including the Portland Museum. Whether you're looking for family-friendly activities or outdoor adventures, Portland has something for everyone to create lasting memories.

  • East End Beach: Enjoy the laid-back atmosphere of East End Beach, where you can relax on sandy shores, soak up the sun, and take in stunning views of the Atlantic Ocean. It's the perfect spot for a seaside picnic or a leisurely stroll along the water's edge.
  • International Cryptozoology Museum: Delve into the intriguing world of cryptozoology at this unique museum. Discover fascinating exhibits dedicated to legendary creatures like Bigfoot and the Loch Ness Monster, offering a blend of culture and curiosity that will captivate your imagination.
  • Maine Narrow Gauge Railroad Company and Museum: Experience a slice of history at this charming museum, showcasing the legacy of Maine's narrow gauge railroads. Ride on vintage trains and explore exhibits that highlight the region's transportation heritage, making it a delightful outing for all ages.

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 SunnyAverageSlightly 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 SunnyModerately LowAverage

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.

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
Higgins Beach, State Theatre and East End Beach

Top hotels in Portland

Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

1230 Congress St Portland ME
Fully refundable
£107
1 Sept - 2 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
£87
8 Sept - 9 Sept
includes taxes & fees
Fireside Inn & Suites Portland
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
£250
30 Aug - 31 Aug
includes taxes & fees
9.4/10 Exceptional! (1,731 reviews)
"Staff outstanding. 2 queen beds turned out to be full size, so very tight sleeping."

Reviewed on 12 Aug 2026

Portland Regency Hotel & Spa
See all 496 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.
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Where to go when
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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.
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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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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.
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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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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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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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What to do in Portland

Sunset Windjammer Cruise Along the Coast of Portland Maine

Sunset Windjammer Cruise Along the Coast of Portland Maine

£58
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

£103
per adult
Portland Explorer: Boat Cruise with Oysters & Prosecco
See all activities in Portland

Frequently asked questions

Why should I book my Portland holiday with Expedia?
Choose Expedia to arrange your next big escape easily and all in one place. Our top tip for landing the best deal on a Portland getaway? Bundle your accommodation, flights and/or car hire into a package holiday. Then add some awesome tours and activities. Many bookings also come with flexible cancellation policies, so there's no need to stress if you have to switch up your itinerary. Round-the-clock help with changing and cancelling your trip is on-hand via our Customer Service Portal link.
When is the best time of year to holiday in Portland?
To enjoy the atmosphere of peak season, take off in March, April and July. September, October and December are typically quieter and a smart idea if you want to get away from the crowds. With average daytime temperatures of -3ºC, January is the coolest month in Portland. The warmest time of year is July, when you can experience average temperatures of 20ºC throughout the day. Whatever the temperature, you'll discover plenty to keep you entertained here.
What are the top hotels for my holiday in Portland?
Travellers visiting Portland often stay in Munjoy Hill. AC Hotel by Marriott Portland Downtown/Waterfront, ME and Portland Harbour Hotel are popular picks in this neighbourhood. But it's not the only vibrant place around town! East End is also a terrific area and where you'll find La Quinta Inn & Suites by Wyndham Portland and The Westin Portland Harborview.
How do I get a cheap holiday to Portland?
Find flights that suit your schedule, add a hotel room to your booking and watch the savings pile up with a Portland holiday. It's that simple! From hotels and flights to hire cars and activities, Expedia makes travelling on a budget easy. And with over 400 airlines and 321,000 properties around the globe to pick from, you won't be short of choice. Learn more about how you can save money on your next holiday when you combine your flight and hotel bookings with Expedia.
What should I do on my Portland holiday?
Offering popular attractions such as Portland Head Light and Portland Museum of Art, a holiday in Portland is full of fun things to see and do. University of Southern Maine and Victoria Mansion are a couple of other sights also worth a look.
What are the best neighbourhoods to stay in when on holiday in Portland?
If you want to find out what makes Portland so popular, Downtown Portland is a great place to start. From this area, you can easily access Portland Museum of Art and Wadsworth-Longfellow House. Another place to consider is Portland Arts District. Known for Portland Museum of Art and Wadsworth-Longfellow House, it's no surprise that many people book a stay here.
Do I need a visa for my Portland holiday?
Check the latest rules on official government websites. Your nationality and whether you're visiting for study, leisure or business will determine if you'll require a visa for Portland. Make yourself familiar with the application process, including the required documentation, turnaround times and fees. Start your application well in advance to allow sufficient time for processing. Some visas may take many weeks or even months to obtain, depending on the country and time of year.
What should I wear on my Portland holiday?
Think about the type of activities planned during your holiday in Portland and travel with pieces that you can easily mix and match. For fashion inspiration or information on any dress codes, look up a few style blogs or relevant social media accounts. Daytime temperatures during January, Portland's coolest month, average -3ºC. July marks this destination's warmest month when the average reaches 20ºC. Our top piece of advice? Take the guesswork out of packing and check the local weather forecast.
What does an Expedia Portland holiday include?
Flights, hotels and a cool car for all your fun road trip adventures. Simply mix and match your favourite bundle and gain access to great discounts. Once you've made your booking, add on some sightseeing tours and watch your savings grow. When it comes to crafting your Portland trip, you're the boss! Explore a wide range of property types and pick one that matches your travel needs. The most in-demand rentals here are private holiday homes and apartments. With Expedia, you can easily tailor-make your Portland escape any way you like.
Does Expedia offer Book Now, Pay Later Portland holidays?
Expedia has joined forces with online lender Klarna to make your next trip a little easier on the wallet. Paying by instalment means you can spread the costs of your dream holiday, leaving you with more money to spend while you're away. Klarna has several payment plans to choose from, so you're sure to find one that works with your budget. Consider these flexible payment options:
  • Pay monthly holidays: Klarna offers convenient monthly payment plans that work for all budgets, so you can have that well-deserved holiday sooner.
  • No-deposit holidays: Clicking the "book now" button is easier with this option. With no upfront fee for your escape, you can Book Now, Pay Later and get on your way.
Can I choose my airline with a Portland Expedia holiday?
Yes — and it's simple too. Expedia has access to more than 400 partner airlines globally. Our packages give you the flexibility to take your pick of available flight, hotel or activity options that fit your needs.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.