Portland Vacation Packages

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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.

Top Portland Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Inn By The Sea

Inn By The Sea

CA $1,834
per person
Sep 25 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
9.6/10 Exceptional! (328 reviews)
Lovely property. Very well maintained and taken care of. The option of pool or beach is a plus. Although we didn’t utilize the activities available each day.. it seemed very family friendly. Definitely will be back but hopefully reserve a bigger room or suite. Charming outdoor seating on the huge lawn but mostly in the sun. An indoor lobby with some comfy seating would be great.

Reviewed on Aug 13, 2026

The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

Downtown Portland
CA $2,144
per person
Sep 25 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
9.6/10 Exceptional! (367 reviews)
Hampton Inn Portland Downtown - Waterfront

Hampton Inn Portland Downtown - Waterfront

Downtown Portland
CA $1,845
per person
Sep 25 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
8.8/10 Excellent! (1,009 reviews)
The Weldon Hotel

The Weldon Hotel

Downtown Portland
CA $2,566
per person
Sep 25 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
9.8/10 Exceptional! (107 reviews)
We had a wonderful stay. Highly recommend!

Reviewed on Aug 19, 2026

The Docent's Collection at 178 Middle Street

The Docent's Collection at 178 Middle Street

Downtown Portland
CA $2,290
per person
Sep 25 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
9.6/10 Exceptional! (48 reviews)

Where to stay in Portland

Find the best Portland areas and neighborhoods for the activities you enjoy most. Learn more about Portland
A tree-lined pathway leading to a brick building with a sign reading "Mercy Hospital Service Entrance".

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.

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 lighthouse on a rocky shore with a sailboat in the distance.

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 large, cream-colored building with white columns and a white picket fence in front.

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.

A red brick building with Gothic architectural features, including pointed arches and a cross on top.

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.

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.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January26.1°F (-3.3°C)Light RainMostly SunnyModerately LowSlightly Low
February27.0°F (-2.8°C)Light RainMostly SunnyModerately LowSlightly Low
March33.4°F (0.8°C)Light RainMostly SunnyAverageSlightly Low
April43.9°F (6.6°C)Light RainMostly SunnyAverageAverage
May54.0°F (12.2°C)Light RainMostly SunnyAverageAverage
June61.9°F (16.6°C)Light RainMostly SunnyAverageAverage
July68.9°F (20.5°C)Light RainMostly SunnyModerately HighSlightly High
August68.5°F (20.3°C)Light RainMostly SunnyModerately HighSlightly High
September62.2°F (16.8°C)Light RainMostly SunnyModerately HighSlightly High
October52.2°F (11.2°C)Light RainMostly SunnyAverageAverage
November41.2°F (5.1°C)Light RainMostly SunnyAverageAverage
December32.9°F (0.5°C)Light RainMostly SunnyModerately LowAverage

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.

Ready to book your vacation to Portland?

Choose your dates

Portland Hotel Deals

Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

1230 Congress St Portland ME
Fully refundable
CA $163
CA $180 total
Sep 7 - Sep 8
includes taxes & fees
Clarion Hotel Portland Airport ME
Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

81 Riverside St Portland ME
Fully refundableReserve now, pay when you stay
CA $153
CA $169 total
Sep 9 - Sep 10
includes taxes & fees
8.2/10 Very good! (1,060 reviews)
"Great experience and highly recommend"

Reviewed on Aug 23, 2026

Fireside Inn & Suites Portland
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
CA $315
CA $348 total
Aug 30 - Aug 31
includes taxes & fees
9.4/10 Exceptional! (1,752 reviews)
"Great location (near shops, restaurants and bars). The bed was extremely comfortable."

Reviewed on Aug 22, 2026

Portland Regency Hotel & Spa
See all 498 properties in Portland
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

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.
See properties
An art gallery with various paintings and sculptures.

Portland Museum of Art

9.2/10 (610 reviews)
Maine’s largest and oldest art institution showcases three centuries of American art and European masters in its architecturally impressive museum complex.
See properties
A lighthouse on a rocky shoreline with a cloudy sky.

University of Southern Maine

8.2/10 (233 reviews)
Explore the campus of University of Southern Maine during your stay in Portland. Stroll along the seaside or attend a sporting event in the area.
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A beach with people sunbathing and swimming, boats in the water, and a rocky shoreline.

East End Beach

9.2/10 (90 reviews)
Swim in the Atlantic Ocean, stroll along the sand-and-pebble shoreline or enjoy a picnic with unbeatable views at Portland’s public beach.
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Thompson's Point

8.8/10 (376 reviews)
Commune with nature and explore the great outdoors at Thompson's Point during your travels in Portland. Stroll along the waterfront or attend a sporting event in the area.
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Cross Insurance Arena

8.6/10 (275 reviews)
Catch an event at Cross Insurance Arena during your trip to Portland. Stroll along the area's waterfront or experience its great live music.
See properties

Hadlock Field

9.8/10 (6 reviews)
Catch an event at Hadlock Field during your trip to Portland. Amble around the area's waterfront or attend a sporting event.
See properties

Merrill Auditorium

8.8/10 (107 reviews)
You can enjoy a show at Merrill Auditorium during your trip to Portland. Stroll along the area's waterfront or experience its acclaimed theater scene.
See properties

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
90% of travellers recommend
Sunset Windjammer Cruise Along the Coast of Portland Maine
Morning Lighthouse Cruise Along the Coast of Portland Maine

Morning Lighthouse Cruise Along the Coast of Portland Maine

CA $83
per adult
Morning Lighthouse Cruise Along the Coast of Portland Maine
See all activities in Portland

Frequently asked questions

How much does a Portland vacation package cost?
Offering excellent value package deals from CA $1,834 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.

Explore a world of travel with Expedia

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