Portland Vacations from $553

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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.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $654, price is now $553 per person
$553
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Portland (PWM)
9.2/10 Wonderful! (1,851 reviews)
each floor had a pantry where you can make coffee. Although the downstairs coffee in the lobby emptied really fast and they didn’t really refill it very often. There’s only one elevator going up to the fourth floor, at least by the lobby. So sometimes it would get crowded. The hotel is centrally located and very close to everything. I would highly recommend.

Reviewed on Oct 27, 2026

Nautical Mile

Nautical Mile

2.5 out of 5
Price was $698, price is now $557 per person
$557
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Portland (PWM)
8.6/10 Excellent! (25 reviews)
I've stayed at the Nautical Mile many times! The rooms are perfect for a get-away! The pool is always ready to cool off in and the people, both working at the Nautical Mile and guests are very friendly.

Reviewed on Sep 8, 2026

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was $897, price is now $745 per person
$745
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Portland (PWM)
9.6/10 Exceptional! (199 reviews)

The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Price was $1,275, price is now $1,093 per person
$1,093
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
8.6/10 Excellent! (1,007 reviews)
The property was very clean and well maintained. The staff were friendly and helpful. It’s the ideal location when attending the Ogunquit Playhouse. We didn’t have time to take advantage of them, but I was impressed by the many amenities available. The complimentary breakfast was adequate.

Reviewed on Oct 26, 2026

Inn By The Sea

Inn By The Sea

4 out of 5
Price was $869, price is now $749 per person
$749
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Portland (PWM)
9.6/10 Exceptional! (342 reviews)

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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
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

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

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)
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.
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What to do in Portland

Sunset Windjammer Cruise Along the Coast of Portland Maine

Sunset Windjammer Cruise Along the Coast of Portland Maine

$77
per adult
92% of travellers recommend
Sunset Windjammer Cruise Along the Coast of Portland Maine
Portland: Casco Bay Morning Lighthouse Cruise

Portland: Casco Bay Morning Lighthouse Cruise

$59
per adult
80% of travellers recommend
Portland: Casco Bay Morning Lighthouse Cruise
Sunset Lighthouse Cruise Along Casco Bay

Sunset Lighthouse Cruise Along Casco Bay

$69
per adult
Sunset Lighthouse Cruise Along Casco Bay
See all activities in Portland

Portland Hotel Deals

The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St Portland ME
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $119 total per night from Nov 18 to Nov 19
$119 total
Nov 18 - Nov 19
Total with taxes and fees
The Westin Portland Harborview
Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
Fully refundable
$83 nightly
The price is $92 total per night from Nov 3 to Nov 4
$92 total
Nov 3 - Nov 4
Total with taxes and fees
Clarion Hotel Portland Airport ME
Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

3 out of 5
81 Riverside St Portland ME
Fully refundableReserve now, pay when you stay
$88 nightly
The price is $97 total per night from Nov 2 to Nov 3
$97 total
Nov 2 - Nov 3
Total with taxes and fees
Fireside Inn & Suites Portland
See all 489 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 $553 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.

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.