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A cityscape with a prominent church steeple, various buildings, and lush green trees.

Portland Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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Top Portland vacation deals

Price found within the past 48 hours. Click for updated prices.
  • Lobby sitting area
    Sept 21 - Sept 25

    Ogunquit River Inn & Suites + Flight

    Moody
    4 nights
    3.0 star property
    9.0/10 - Wonderful (1,009 reviews)
    "Pros: Quiet , clean pool , clean grounds , balcony , close to beaches and shopping areas, nice staff. Cons: terrible internet connection , TVs kept freezing, carpet, mold in bathroom, breakfast was not good, 10-15 min waits to both check in and check out."
    Reviewed July 30, 2026
    Roundtrip • Montreal (YUL) - Portland (PWM)
    YUL - BOS • 1 stop BOS - YUL • 1 stop
    CA $1,173
    CA $881
    per traveller
    found 1 day ago
    Ogunquit River Inn & Suites
  • Indoor spa tub
    Sept 21 - Sept 25

    The Meadowmere Resort + Flight

    Ogunquit
    4 nights
    2.5 star property
    8.6/10 - Excellent (1,004 reviews)
    "We were in the clover, the room was well decorated but not so spacious. We loved all the possibilities there is to do at the resort. The free breakfast is croissants, danishes, fruits and coffee near the lobby. Loved how walkable it was to the the heart of Ogunquit and the beach."
    Reviewed July 30, 2026
    Roundtrip • Montreal (YUL) - Portland (PWM)
    YUL - BOS • 1 stop BOS - YUL • 1 stop
    CA $1,346
    CA $1,027
    per traveller
    found 1 day ago
    The Meadowmere Resort
  • Restaurant
    Sept 13 - Sept 18

    Portland Harbor Hotel + Flight

    Downtown Portland
    5 nights
    4.0 star property
    9.2/10 - Wonderful (1,794 reviews)
    "The property is in a great location minutes walk away from stores, great food and sights and trips. But as a property itself it lacks amenities and maintenance levels to fully justify the high seasonal pricing"
    Reviewed July 28, 2026
    Roundtrip • Montreal (YUL) - Portland (PWM)
    YUL - PWM • 1 stop PWM - YUL • 1 stop
    CA $2,839
    CA $2,167
    per traveller
    found 1 day ago
    Portland Harbor Hotel
  • Exterior
    Sept 13 - Sept 18

    Inn at Diamond Cove + Flight

    Portland
    5 nights
    3.5 star property
    8.8/10 - Excellent (202 reviews)
    Roundtrip • Montreal (YUL) - Portland (PWM)
    YUL - PWM • 1 stop PWM - YUL • 1 stop
    CA $1,945
    CA $1,522
    per traveller
    found 1 day ago
    Inn at Diamond Cove
  • Front of property
    Sept 13 - Sept 18

    Evalina Hotel + Flight

    Downtown Portland
    5 nights
    2.5 star property
    10/10 - Exceptional (7 reviews)
    "The accommodations were perfect for a family of 4. The 2 bedroom/2 bath was very spacious, very well laid out and in an excellent location. We really enjoyed our stay!"
    Reviewed July 28, 2026
    Roundtrip • Montreal (YUL) - Portland (PWM)
    YUL - PWM • 1 stop PWM - YUL • 1 stop
    CA $3,717
    CA $3,130
    per traveller
    found 1 day ago
    Evalina Hotel

Where to stay in Portland

Find the best Portland areas and neighborhoods for the activities you enjoy most. Learn more about Portland
Learn more about Portland
A marina with boats docked, a wooden pier, and a red brick building with balconies.

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.
A building with a large arched window and a sign that reads "STATE".

Downtown Portland

Downtown Portland combines New England charm with a lively waterfront scene. Cobblestone streets wind past brick buildings housing artisan galleries, craft breweries, and seafood restaurants along Casco Bay. The historic district buzzes with local culture and maritime heritage. Explore museums like the Portland Museum of Art or catch performances at Merrill Auditorium. The working harbour offers scenic walks and ferry trips to nearby islands. With its walkable layout, vibrant dining scene, and shopping boutiques, this area perfectly captures Maine's coastal spirit.
A calm lake with several kayaks lined up on the shore and boats in the water.

East End

Portland's East End offers a picturesque coastal escape with its stunning 2.1-mile Eastern Promenade trail. Panoramic views of Casco Bay and offshore islands create the perfect backdrop for morning walks or sunset picnics. Victorian and Colonial Revival homes line tree-shaded streets that blend historic charm with modern flair. This quiet residential haven has evolved into a creative hub with artisanal coffee shops and craft breweries. Visitors can explore the Portland Observatory or relax at East End Beach. The area maintains its authentic local vibe while welcoming travellers seeking a genuine Portland experience.
A historic building with ornate architecture, large windows, and a prominent tower.

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.
A historic building with a sign reading "Portland Museum of Art McLellan House."

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.

Discover the most popular places to visit in Portland

A multi-story brick building with a large arched window and a sign that reads "STATE".

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.

What to do in Portland

Sunset Windjammer Cruise Along the Coast of Portland Maine

Sunset Windjammer Cruise Along the Coast of Portland Maine

CA $109
per adult
88% of travellers recommend
Sunset Windjammer Cruise Along the Coast of Portland Maine
See all activities in Portland

Portland Hotel Deals

Free daily on-the-go breakfast

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med
3.0 star property
2.2 km from Portland
8.4 out of 10, Very good, (2,190 reviews)
"We only stayed overnight. The room was clean and staff was nice"
The price is CA $237
CA $262 total
includes taxes & fees
Aug 23 - Aug 24
La Quinta Inn & Suites by Wyndham Portland DT/Maine Med
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.
See all properties in Portland

Frequently Asked Questions

How much does a Portland vacation package cost?

Offering excellent value package deals from CA $881 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 many days is enough for Portland?

We'd suggest booking a Portland vacation for around 2 days. This will give you enough time to tick off popular sights including State Theatre and Portland Museum of Art, and also explore neighbourhoods like Downtown Portland and Old Port. You could even fit in a day trip or two outside of Portland.

Is it worth booking a vacation package to Portland?

During your Portland vacation, you can look forward to experiencing some top-notch walking trails and culture. Leave enough room in your itinerary to check out leading sights like Thompson's Point and State Theatre.

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?

  1. Pick the ideal time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to go to Portland.
  2. 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.
  3. 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.
  4. 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.

Book with confidence

Things to do in and around Portland

Portland, Maine, offers a delightful blend of outdoor adventures, scenic views, and family-friendly activities. Visitors can enjoy beach vacations, explore fishing piers, and engage in additional sightseeing. The city also boasts an array of entertainment options, including an arena, theatre performances, and music concerts, alongside great shopping opportunities that showcase local craftsmanship and flavours.

Shopping

In Portland, visit the Maine Mall, just 6.4km away, for a vibrant shopping experience with a variety of stores and entertainment. If you're up for a drive, check out the LL Bean Flagship Store and Marden's Surplus and Salvage, located 16 and 27.4km away, respectively.

Recreation

In Portland, indulge in the cultural ambiance of the State Theatre, where live performances create a romantic atmosphere. Experience the vibrant energy at Thompson's Point with its lively music concerts. For sports enthusiasts, Hadlock Field offers an exciting venue to enjoy thrilling games in a community-focused environment.

Adventure

Experience the vibrant atmosphere at Bayside Bowl with arcade games and bowling fun. Get your adrenaline pumping at Racket & Fitness Center with various adventure activities. For a scenic hike, venture to MAGAN Trailhead for stunning outdoor views, located 11.3km from Portland.

Nightlife

In Portland, Maine, enjoy vibrant nightlife at venues like Old Port, known for its lively bars and seafood restaurants. Visit Congress Street for eclectic music spots and cozy pubs. Don’t miss unique craft breweries and waterfront views that enhance the city's charming evening atmosphere.

Find the best attractions in Portland

Portland, Maine, is perfect for a family vacation, offering a mix of outdoor adventures and cultural experiences. Explore stunning beaches, historic houses, and vibrant entertainment venues. Don't miss the Portland Museum for a taste of local culture. With a variety of attractions catering to families and outdoor enthusiasts, you'll find plenty to enjoy in this charming coastal city.

  • Portland Museum of Art: This museum is a cultural gem, featuring an impressive collection of American, European, and contemporary art. Its stunning architecture and rotating exhibitions provide a unique insight into the art world, making it a must-see for culture enthusiasts.
  • East End Beach: Enjoy the sun and surf at East End Beach, a charming sandy spot perfect for relaxation or a beach day. With picturesque views of Casco Bay, it's an ideal location for swimming, picnicking, or simply soaking in the coastal vibe.
  • Cathedral of the Immaculate Conception: This stunning cathedral showcases beautiful Gothic architecture and intricate stained glass windows. Its serene atmosphere and rich history make it a peaceful place for reflection and appreciation of its artistic details.

Best time to go to Portland

The best time to visit Portland is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are moderately high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are moderately low and weather is mostly sunny with light rain.

Tips to save on your trip to Portland

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling to Portland during the low season (January to March) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.