Portland Vacations
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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
5 out of top 10 points of interest in this area
Downtown Portland is known for its captivating waterfront views, and with sights like Cross Insurance Arena and Merrill Auditorium, you won't get bored spending a day wandering around this part of Portland.
Old Port
Cobblestone streets, 19th-century brick buildings, and fishing piers define this district, offering boutiques, restaurants, and bars. Explore Post Office Park, Tommy's Park with its large mural, and stroll the Eastern Promenade Trail to East End Beach.
West End
Distinguished by its well-preserved Victorian architecture, this downtown Portland neighborhood boasts the scenic Western Promenade park, offering views of the White Mountains, and several historic structures, such as the Gothic House and Morrill Mansion.
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
Bordered by Franklin Street and Washington Avenue, East Bayside offers a community arts venue, Mayo Street Arts, and the relaxing green space of Kennedy Park. Explore nearby Old Port and Munjoy Hill.
Find the Best Portland Vacation Packages
Portland Hotel Deals
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundableReserve now, pay when you stay
SAR 266
SAR 294 total
1 Nov - 2 Nov
includes taxes & fees
8.2/10 Very Good! (1,742 reviews)
"A nice place to stay"
Reviewed on 1 October 2026
Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
SAR 636
SAR 847 total
1 Nov - 2 Nov
includes taxes & fees
Fireside Inn & Suites Portland
81 Riverside St Portland ME
Fully refundableReserve now, pay when you stay
SAR 316
SAR 350 total
29 Oct - 30 Oct
includes taxes & fees
8.2/10 Very Good! (1,027 reviews)
"Hotel was worth the price. Staff was friendly and helpful at check-in. Room was spacious, comfortable, and clean. We were up graded to a courtyard facing room and it was quiet. Overall, the hotel was worth the price and satisfactory."
Reviewed on 30 September 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.
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.
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 Center and Portland Commons before venturing into the nearby arts and culinary scene.
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.
Cross Insurance Arena
8.6/10 (275 reviews)
This downtown 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.
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.
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.
Maine Narrow Gauge Railroad
You can spend an afternoon studying the exhibits at Maine Narrow Gauge Railroad in Portland. Experience the area's acclaimed theater scene and great live music.
Frequently asked questions
How much does a Portland vacation package cost?
Offering excellent value package deals on Expedia, you'll be surprised at how little a vacation to Portland costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Portland?
You can typically find reduced prices and greater availability in January, February and March. Explore our cheap Portland vacation packages and you could score some great off-season deals.
How to find the best Portland package deals?
Bagging a cheap Portland package deal is easy with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your maximum budget, add a few filters and see what's available. You can personalize your search by "Amenities," "Property type," "Popular locations" and more. Order the results by "Price: low to high" to view the most affordable Portland package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Portland vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging accommodations and flights individually. Better still, you can tailor your Portland trip to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Portland?
If you've got your Portland travel dates locked in, book as early as you can to snap up some unbeatable deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spontaneous adventures? Our last-minute deals are great for impromptu escapes.
How to plan a trip to Portland?
- Pick the ideal time to travel: Your schedule, favorite season and the type of weather you like can all impact your decision on when to go to Portland.
- Calculate your budget: Ensure you have enough money to pay for everything from transportation and food to activities and flights. Your hotel will likely be the biggest expense during your trip to Portland.
- Set the duration of your trip: Start by listing all the activities and sights you'd like to get to in Portland. Then, estimate how long you'll need for each, as well as any travel time.
- Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a tailored Portland vacation package.
