Portland Vacations from $731
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Your Portland Vacation
When a break in the city is calling, answer it with a vacation package to Portland. The neighborhood of Parkside, which is great for festivals, markets and walking, makes a fantastic base for your adventures. Fill your free time with tours of Portland Head Light, University of Southern Maine and Portland Museum of Art, some of the top attractions you just have to see during your trip to Portland. Don't put off your visit to this destination any longer. Your perfect Portland vacation is just a few clicks away with Expedia.
The Latest Portland vacation packages
Price found within the past 48 hours. Click for updated prices.
The Docent's Collection at 178 Middle Street
Downtown Portland
$731
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9.6/10 Exceptional! (70 reviews)
This place is gorgeous! I highly recommend it. Beautiful modern design with everything you might need. Great central location. A bit hard to find. Parking was A lot! But made life easier. Will stay here again.
Reviewed on Oct 6, 2026
Evalina Hotel
Downtown Portland
$1,195
per person
Dec 27 - Dec 30
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
10/10 Exceptional! (13 reviews)
Centrally located in the Old Port, with views of the harbor, this was a last minute — therefore pricey — excellent find for a fall weekend getaway. Stylish, elegant rehab of 19th century granite industrial building. Whimsical decor notes referring to 19th century owner Evalina Fox. Nicely appointed kitchenette — though if you came to Portland for the foodie scene, you might end up just using it for breakfast, as we did. Only sour note was the disco music (coming in via the ventilation system?) from a nearby establishment audible during business hours. Well, if you pick a hotel in the middle of things, you get the noise and bustle that comes from being in the middle of things. That said, we’d come again, but shoot for a penthouse/upper floor unit farther from the street-level mania.
Reviewed on Oct 5, 2026
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
Known for its culinary delights, inspiring art and live music, the heart of Maine’s largest city is an exciting location.
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.
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.
What to do in Portland
Sunset Windjammer Cruise Along the Coast of Portland Maine
$77
per adult
90% of travellers recommend
Portland: Casco Bay Morning Lighthouse Cruise
$59
per adult
80% of travellers recommend
Portland Hotel Deals
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundableReserve now, pay when you stay
$71 nightly
$78 total
Nov 1 - Nov 2
Total with taxes and fees
8.2/10 Very Good! (1,755 reviews)
"Clean room, just very outdated building/room. Small elevator. Floor in room by door was warped (?) door hard to open /close."
Reviewed on Oct 7, 2026
The Westin Portland Harborview
157 High St Portland ME
Fully refundableReserve now, pay when you stay
$135 nightly
$149 total
Nov 1 - Nov 2
Total with taxes and fees
9/10 Wonderful! (1,009 reviews)
"Wonderful, historic building. Clean room. Great staff. Design starting to look a bit dated."
Reviewed on Oct 6, 2026
Fireside Inn & Suites Portland
81 Riverside St Portland ME
Fully refundableReserve now, pay when you stay
$86 nightly
$95 total
Oct 29 - Oct 30
Total with taxes and fees
8.2/10 Very Good! (1,015 reviews)
"S for"
Reviewed on Oct 6, 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.
Find the Best Portland Vacation Packages
Portland Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Portland Intl. Jetport Airport (PWM) |
Population | 66,900 |
Max Temp Winter | 30ºF |
Max Temp Summer | 75ºF |
Top Sights | State Theatre, Higgins Beach and East End Beach |
More vacations you might like
Frequently asked questions
How much does a Portland vacation package cost?
You'll find cheap prices from $731 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?
If you're looking to score a cheap Portland vacation package, consider visiting in September, October and December. You'll usually find lower rates on airfares and hotels during these months — perfect for budget-conscious travelers.
How many days is enough for Portland?
Allow around 2 days for your Portland vacation if you want to discover all that makes this place special. Explore popular areas, including Nasons Corner and East Bayside. Then check out top attractions like East End Beach and Sand Beach. With a clever itinerary, you'll be kept busy with room for some downtime too. Want to go beyond Portland? Consider squeezing in an excursion or two.
Is it worth booking a vacation package to Portland?
Known for its walking trails, culture and plenty of other highlights, you can be certain Portland is a good vacation destination. Some of the top attractions to add to your itinerary? Don't miss Portland Museum of Art and Victoria Mansion during your Portland vacation.
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?
- Choose when to get away: Check your calendar and get packing. Your favorite time of year and the type of activities on offer will also help you decide when to visit Portland.
- Set a budget: Factor in costs such as flights, food and transportation when working out how much to save for your trip to Portland. Then, select a property that works with your budget, whether that's a wallet-friendly option or a high-end getaway.
- Explore Portland with our trip planning tool: Gain insights into the top attractions and best hotels for your trip to Portland. You can also save your must-visit places, collaborate with friends and family and organize your plans in one place.
- Decide your trip length: Consider how much time you want to spend discovering Portland. Plan your days so you can get to all the experiences and attractions you're interested in at a comfortable pace.
- Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a tailored Portland vacation package.
- Book any activities or day trips: Now to the fun part — organizing everything you want to see and do. Explore some of the best things to do in Portland and reserve your tickets in advance to save time (and maybe some cash too!).
Does Expedia offer Book Now, Pay Later Portland vacation packages?
Jet off on your dream escape to Portland with help from Expedia's Book Now, Pay Later vacations. There's no need to save like crazy or hold off until the next payday — we've teamed up with online lender Affirm to give you flexibility with your finances. Our vacation packages with payment plans mean you can split the cost across 3, 6 or 12 months. With no hidden or late payment fees, it's a breeze to stick to your budget and snap up bargains while they last.
Explore a world of travel with Expedia
- Hotels near Downtown Portland
- Hotels near Old Port
- Hotels near Cathedral of the Immaculate Conception
- Hotels near Merrill Auditorium
- Hotels near Maine Jewish Museum
- Hotels near N.W. Barrett Gallery
- Hotels near East Bayside
- Cheap Hotels in Old Port
- Hotels near West Bayside
- Hotels near Monument Square
- Hotels with Free Parking in Old Port
- Hotels near Cross Insurance Arena
- Pet-Friendly Hotels in Old Port
- Hotels with Hot Tubs in Old Port
- Boutique Hotels in Old Port
- Hotels with Fireplaces in Old Port
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- Romantic Hotels in Old Port
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- Historic Hotels in Old Port
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- Hotels with an Indoor Pool in Old Port
- Hotels with Free Airport Shuttle in Old Port
- 5 Star Hotels in Old Port
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- Honeymoon Resorts & in Old Port
- Hotels with Hot Tubs in Downtown Portland
- Hotels near Casco Bay Lines Ferry Terminal
- Hotels with Balconies in Downtown Portland
- Hotels with Connecting Rooms in Downtown Portland
- Pet-Friendly Hotels in Downtown Portland
- Oceanfront Hotels in Downtown Portland
- Luxury Hotels in Downtown Portland
- Hotel Wedding Venues Hotels in Downtown Portland
- Cheap Hotels in Downtown Portland
- Historic Hotels in Downtown Portland
- Hotels with Free Airport Shuttle in Downtown Portland
- Hotels with Free Parking in Downtown Portland
- Hotels with Fireplaces in Downtown Portland
- 3 Star Hotels in Downtown Portland
- Family Hotels in Downtown Portland
- Romantic Hotels in Downtown Portland
- Hotels with Laundry Facilities in Downtown Portland
- Hotels with an Outdoor Pool in Downtown Portland
- Hotels with Free Breakfast in Downtown Portland
- Hotels with an Indoor Pool in Downtown Portland
- Hotels with a Pool in Downtown Portland
- Maine Jewish Museum
- Merrill Auditorium
- Casco Bay Lines Ferry Terminal
- Visit Old Port
- N.w. Barrett Gallery
- Maine Sports Hall of Fame
- Old Port Vacations
- Wadsworth-Longfellow House
- Downtown Portland Vacations
- Maine Historical Society
- Center for Maine History
- Cross Insurance Arena
- Museum of African Culture
- Maine College of Art
- Space Gallery
- Maine Narrow Gauge Railroad Company and Museum
- Victoria Mansion
- Portland Museum of Art
- Charles Q. Clapp House
- East End Beach
- State Theatre
- Mclellan-Sweat Mansion
- Mclellan-Sweat House
- International Cryptozoology Museum
- Eastern Promenade
- Portland Fire Museum
- State Street Church
- Cathedral Church of Saint Luke
- Center for Cultural Exchange
- Visit Downtown Portland
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
