Portland Holidays

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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.

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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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Portland Holiday

Our pick of the best Portland Hotel Deals

Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

1230 Congress St Portland ME
NZ$227
28 Sept - 29 Sept
includes taxes & fees
8.2/10 Very good! (1,693 reviews)
"Perfect place to stay if you're going to a concert at Thompson's Point! Very outdated but clean. Would stay here again!"

Reviewed on 16 Sept 2026

Clarion Hotel Portland Airport ME
Portland Harbor Hotel

Portland Harbor Hotel

468 Fore Street Portland ME
NZ$687
20 Sept - 21 Sept
includes taxes & fees
Portland Harbor Hotel
Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

81 Riverside St Portland ME
Fully refundableReserve now, pay when you stay
NZ$217
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

NZ$99
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

NZ$129
per adult
90% of travellers recommend
Sunset Windjammer Cruise Along the Coast of Portland Maine
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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.