Portland Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$134 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

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

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (1,758 reviews)
Hotel was very clean, room was nice, bed was comfy and it was very peaceful!

Reviewed on 26 Jan, 2026

Portland Harbor Hotel
Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
Fully refundableReserve now, pay when you stay
The price is S$108 per night from 16 Feb to 17 Feb
S$108
16 Feb - 17 Feb
includes taxes & fees
8/10 Very Good! (1,339 reviews)
A++ Quiet. Amazing comfortable king bed. Housekeeping dept. excellent. Front desk dept. excellent. Love it here

Reviewed on 27 Jan, 2026

Clarion Hotel Portland Airport ME
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
9.4/10 Exceptional! (1,576 reviews)
The room was impeccable, the restaurant was delicious and perfect location

Reviewed on 29 Jan, 2026

Portland Regency Hotel & Spa
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.

Popular places to visit

What to do in Portland

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.