Portland Vacations from $457

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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.
Admiral Peary Inn

Admiral Peary Inn

3 out of 5
Save 100% on your flight
per person
Jul 31 - Aug 5
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
9/10 Wonderful! (25 reviews)
Cherri was very nice and welcoming. It was a neat old house they have made comfortable and welcoming.

Reviewed on May 27, 2025

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Save 100% on your flight
per person
Sep 20 - Sep 27
found 7 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.2/10 Wonderful! (1,523 reviews)
Staff is super friendly and helpful. Love the walking distance of shops and eateries.

Reviewed on Jun 28, 2025

Chebeague Island Inn

Chebeague Island Inn

4 out of 5
Save 100% on your flight
per person
Sep 22 - Sep 26
found 16 hours ago
Roundtrip flight included
Minneapolis (MSP) to Portland (PWM)
8.8/10 Excellent! (71 reviews)
Met our expectations

Reviewed on Sep 9, 2024

The Docent's Collection

The Docent's Collection

3.5 out of 5
Downtown Portland
Save 100% on your flight
per person
Aug 11 - Aug 15
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9.6/10 Exceptional! (207 reviews)
Very impressed with the facility. Centrally located. We had a bumpy start with the contact-less virtual check-in. But now that we know what needs to be done, it will be easier next time for us. Especially nice for anyone who is traveling on business and expects an extended stay in the area.

Reviewed on Jun 20, 2025

Nautical Mile

Nautical Mile

2.5 out of 5
Save 100% on your flight
per person
Aug 19 - Aug 21
found 15 hours ago
Roundtrip flight included
Philadelphia (PHL) to Portland (PWM)
8.4/10 Very Good! (12 reviews)
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te-neigborhood.subtitle Learn more about Portland
State Street Church

Downtown Portland

5 out of top 10 points of interest in this area
4.5/5(326 area reviews)

Known for its culinary delights, inspiring art and live music, the heart of Maine’s largest city is an exciting location.

Find hotels in Downtown Portland

Discover the most popular places to visit in Portland

State Theatre showing street scenes as well as an individual femail

State Theatre

4.5/5(88 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.

State Theatre
East End Beach which includes general coastal views and a beach as well as a small group of people

East End Beach

Swim in the Atlantic Ocean, stroll along the sand-and-pebble shoreline or enjoy a picnic with unbeatable views at Portland’s public beach.

East End Beach
Portland Museum of Art showing art and interior views as well as a small group of people

Portland Museum of Art

4.5/5(255 reviews)

Maine’s largest and oldest art institution showcases three centuries of American art and European masters in its architecturally impressive museum complex.

Portland Museum of Art

What to do in Portland

Portland Downtown Highlights: "The Golden Adventure" Exploration Game

Downtown Golden Adventure Quest Experience in Portland

$9
per adult
Downtown Golden Adventure Quest Experience in Portland
Portland: Schooner Tall Ship Cruise on Casco Bay

Portland: Schooner Tall Ship Cruise on Casco Bay

$107
per adult
Portland: Schooner Tall Ship Cruise on Casco Bay
Sunset Lighthouse Cruise Tour from Casco Bay

Sunset Lighthouse Cruise Tour from Casco Bay

$56
per adult
90% of travellers recommend
Sunset Lighthouse Cruise Tour from Casco Bay
See all activities in Portland

Portland Hotel Deals

Hyatt Place Portland Downtown - Old Port Square
Hyatt Place Portland Downtown - Old Port Square
3 out of 5
433 Fore St, Portland, ME
Fully refundableReserve now, pay when you stay
$265 nightly
The price is $293 total per night from Jun 30 to Jul 1
$293 total
Jun 30 - Jul 1
Total includes taxes and fees
8.8/10 Excellent! (1,146 reviews)
"The location is perfect for a day in the city. Close to everything. The staff was friendly. The free shuttle to the airport was easy to arrange with the service offered 24 hours. I was transported at 3:20 am to the airport saving the cost of an Uber and assured safety at the hour. The gym was under ..."

Reviewed on Jun 23, 2025

Hyatt Place Portland Downtown - Old Port Square
Clarion Hotel Portland
Clarion Hotel Portland
2.5 out of 5
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $168 total per night from Jul 1 to Jul 2
$168 total
Jul 1 - Jul 2
Total includes taxes and fees
7.8/10 Good! (1,001 reviews)
"Shower could use a good grout cleaning. Free coffee in the morning would be nice"

Reviewed on Jun 26, 2025

Clarion Hotel Portland
Portland Regency Hotel & Spa
Portland Regency Hotel & Spa
3.5 out of 5
20 Milk Street, Portland, ME
$220 nightly
The price is $244 total per night from Jun 30 to Jul 1
$244 total
Jun 30 - Jul 1
Total includes taxes and fees
9.2/10 Wonderful! (1,330 reviews)
Hotel stay
"From the minute we pullednin the staff were kind and very helpful. We loved the garden cafe accros from the hotel, its part of it. Great food and drinks. Staff again were so friendly. Above and beyound staff. Were kocals and had a night away, and it was so worth it."

Reviewed on Jun 28, 2025

Portland Regency Hotel & Spa
See all 501 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.

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

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Frequently asked questions

How much does a Portland vacation package cost?
You'll find cheap prices from $457 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.
  5. 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.
  6. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.