Downtown Portland Holidays
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Your Downtown Portland Holiday
Book your holiday package to Downtown Portland and get ready to enjoy its markets and more. Whether you're searching for adventure or relaxation, you'll find it in this appealing neighbourhood. Some popular nearby attractions to check out during your trip to Downtown Portland include Portland Museum of Art, University of Southern Maine and Victoria Mansion. Expedia is here to help put your travel plans into action. Book your perfect Downtown Portland holiday today.
Our guide on where to stay in Downtown Portland
Find the best Downtown Portland areas and neighborhoods for the activities you enjoy most. Learn more about Downtown Portland
Old Port
Explore the cobblestone streets in Portland’s historic district, which combines a wealth of history with a thoroughly modern city experience.
West End
If you're spending some time in West End, Victoria Mansion and Portland Fire Museum are top sights worth seeing.
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.
West Bayside
When in West Bayside, you can plan a visit to Merrill Auditorium and Cross Insurance Arena, some noteworthy sights in the nearby area.
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.
Our pick of the best Downtown Portland Hotel Deals
The Westin Portland Harborview
157 High St Portland ME
Fully refundableReserve now, pay when you stay
AU$170
18 Nov - 19 Nov
includes taxes & fees
Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
AU$264
22 Nov - 23 Nov
includes taxes & fees
Holiday Inn Portland-By the Bay by IHG
88 Spring St Portland ME
Fully refundable
AU$138
22 Nov - 23 Nov
includes taxes & fees
9/10 Wonderful! (1,659 reviews)
"I stayed here twice recently on a trip to Maine for one night, each time either arriving or about to depart my time in Maine. There were other people with me, and we had booked a total of 4 rooms each time. On both experiences the check in process was extremely slow. There was one person working ..."
Reviewed on 21 Oct 2026
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.
Frequently asked questions
How much does a Downtown Portland holiday package cost?
The most affordable Downtown Portland package is , so your dream escape can become a reality — without spending a fortune. Combine flights, hotels and car rentals to build a package that fits you.
How do I get a cheap travel package to Downtown Portland?
Bundle your flights and hotels, add on extras such as tours, and save with a Downtown Portland holiday package. You won't just walk away with impressive discounts on your adventure — you'll have plenty of choice too. When you book with Expedia, you can choose from more than 550 airlines and 1 000 000 properties globally. Your next epic adventure begins right here, right now!
Where should I stay in Downtown Portland?
Take the leg work out of sightseeing by staying right around the corner from Downtown Portland's big attractions. University of Southern Maine and Portland Museum of Art are two of the best in this neighbourhood.
What are the top hotels in Downtown Portland?
Make a reservation at The Docents Collection. It's one of the neighbourhood's most sought-after properties. Another highly rated option in Downtown Portland is Canopy by Hilton Portland Waterfront.
How far in advance should I book my Downtown Portland holiday?
It's difficult to pick the perfect time for airfares, but we usually say the earlier, the better. Many international flights on Expedia become available to compare up to a year in advance. If you're unable to do so, don't worry. Bargain prices appear from time to time just weeks before departure dates.
What does an Expedia Downtown Portland travel package include?
You can select from any combination of hotels, rental cars and flights. Once you've made your booking, you can add the fun stuff like experiences and tours. Want to pick your fare class? That's also possible. The choice is yours when it comes to putting together your dream Downtown Portland getaway.
What should I know before booking a Downtown Portland travel package?
Our prices are always low. However, you'll snap up even more bargains if you book your hotels, flights and car rentals together. With an Expedia travel package, you'll always get transparent pricing and a great range of choice.
Can I choose my airline with a Downtown Portland Expedia holiday package?
Yes — that's the beauty of an Expedia package. You're in control. We have more than 550 airline partners around the world, so you have lots of choice when arranging your Downtown Portland trip.
If I'm not able to travel, can I cancel my Downtown Portland holiday package?
Plans can change suddenly, so yes, you can. You may be able to cancel or amend your Downtown Portland holiday package at no cost within 24 hours of booking. For bookings older than that, you can still make changes, but your hotel, car rental company or airline may impose a charge. Want more information? Take a look at our Customer Service Portal. We're here to help make sure your trip goes off without a hitch.
Stay near popular Downtown Portland attractions
State Theatre
8.8/10 (392 reviews)
The beautiful mix of architectural styles, from Art Deco to Moorish, makes this newly renovated performing arts venue one of New England’s best.
Portland Museum of Art
9.2/10 (610 reviews)
Maine’s largest and oldest art institution showcases three centuries of American art and European masters in its architecturally impressive museum complex.
Photo by Tim Thomas
Maine College of Art
10.0/10 (2 reviews)
You can spend time exploring the galleries in Maine College of Art during your trip to Portland. Experience the area's acclaimed theatre scene and great live music.
State Street Church
Portland’s history of religious tolerance finds its place in a Gothic Revival building at the city center, perfect for attending religious services while on vacation.
Cross Insurance Arena
8.6/10 (275 reviews)
Catch an event at Cross Insurance Arena during your trip to Portland. Stroll along the area's waterfront or experience its great live music.
Merrill Auditorium
8.8/10 (107 reviews)
You can enjoy a show at Merrill Auditorium during your trip to Portland. Stroll along the area's waterfront or experience its entertainment choices.
Monument Square
8.0/10 (1 review)
Find out about the history of Portland with a stop at Monument Square. Stroll along the area's waterfront or experience its acclaimed theatre scene.
Fore Street Gallery
You can spend an afternoon exploring the galleries in Fore Street Gallery during your travels in Portland. Experience the area's entertainment choices and great live music.
Activities
Vintage Fire Truck Sightseeing Tour of Portland Maine
AU$63
per adult
98% of travellers recommend
Afternoon Windjammer Cruise Along the Coast of Portland Maine
AU$97
per adult
96% of travellers recommend
Sunset Windjammer Cruise Along the Coast of Portland Maine
AU$108
per adult
90% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.