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 refundable
NT$4,183
NT$4,628 total
Sep 1 - Sep 2
includes taxes & fees
8/10 Very Good! (1,630 reviews)
"Good for two days"
Reviewed on 2026/8/20
Fireside Inn & Suites Portland
81 Riverside St Portland ME
Fully refundableReserve now, pay when you stay
NT$3,323
NT$3,677 total
Sep 1 - Sep 2
includes taxes & fees
Portland Regency Hotel & Spa
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
NT$9,696
NT$10,728 total
Sep 7 - Sep 8
includes taxes & fees
9.4/10 Exceptional! (1,746 reviews)
"Wonderful hotel in the heart of it all. The shuttle service from the airport was amazing."
Reviewed on 2026/8/20
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 Center 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 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.
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.
Frequently asked questions
How much does a Portland vacation 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 vacation 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 vacation packages and you could score some great off-season discounts.
How many days is enough for Portland?
We recommend booking a Portland vacation 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 neighborhoods 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 vacation package to Portland?
During your Portland vacation, 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 vacation as a package?
You can enjoy significant savings on your Portland retreat by booking a personalized vacation 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 vacation 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, favorite 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 customized Portland vacation package.
Explore a world of travel with Expedia
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- Wadsworth-Longfellow House
- Eastern Promenade
- Nonesuch River Golf Club
- Little John Island Preserve
- International Cryptozoology Museum
- Maine Medical Center
- East End Beach
- Quarry Run Dog Park
- Land's End Gift Shop
- Visit Great Diamond Island
- Marden's Surplus and Salvage
- Funtown Splashtown USA
- Maine Jewish Museum
- Mast Landing Sanctuary
- Pirate's Cove
- Cliff Walk
- Fort Williams Park
- Charles Q. Clapp House
- Desert of Maine
- Monkey Trunks Extreme Aerial Adventure Park
- Biddeford-Saco Country Club
- Yarmouth Vacations
- Aquaboggan Water Park
- East Prom Trail
- Goddard Mansion
- Gilsland Farm Audubon Center
- Visit Portland
- Ferry Beach State Park
- Portland Head Light
- Biddeford Vacations
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
