Portland Holidays
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Where to stay in Portland
Find the best Portland areas and neighborhoods for the activities you enjoy most. Learn more about Portland
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.
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.
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.
Top hotels in Portland
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundable
Rp2.346.121
Rp2.595.749 total
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very good! (1,611 reviews)
"The wallpaper coming off the walls. Dust at every corner, my throat was inching from mold I believe. The ceiling was stained from water leak."
Reviewed on 8 Aug 2026
Portland Regency Hotel & Spa
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
Rp5.461.270
Rp6.042.385 total
8 Sept - 9 Sept
includes taxes & fees
9.4/10 Exceptional! (1,725 reviews)
"Great location. Beautiful historic property. I felt updated and modernized. Definitely recommend."
Reviewed on 8 Aug 2026
Fireside Inn & Suites Portland
81 Riverside St Portland ME
Fully refundableReserve now, pay when you stay
Rp1.897.082
Rp2.098.960 total
8 Sept - 9 Sept
includes taxes & fees
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
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.
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.
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.
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.
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.
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.
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.
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.
What to do in Portland
Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour
Rp175.288
per traveller
Portland Explorer: Boat Cruise with Oysters & Prosecco
Rp2.474.905
per adult
Sunset Windjammer Cruise Along the Coast of Portland Maine
Rp1.391.005
per adult
90% of travellers recommend
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?
- 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.
- 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.
- 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.
- 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
