Portland Vacations from $638

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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.
Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Moody
Save 100% on your flight
Price was $989, price is now $638 per person
$638
per person
Sep 23 - Sep 28
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9/10 Wonderful! (1,020 reviews)
The room was on an upper floor with no elevator, so it did make carrying luggage up and down the stairs difficult. But the room was spacious and clean with a nice view of the river. Conveniently located right on Highway 1.

Reviewed on Jul 21, 2026

The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Save 100% on your flight
Price was $1,358, price is now $881 per person
$881
per person
Sep 23 - Sep 28
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
8.6/10 Excellent! (1,000 reviews)

Evalina Hotel

Evalina Hotel

2.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $2,494, price is now $1,708 per person
$1,708
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
10/10 Exceptional! (5 reviews)
It was a spacious, clean, well thought out space with all the expected amenities. The location is ideal, and the hotel is truly a treasure.

Reviewed on Jun 28, 2026

Cliff House Maine

Cliff House Maine

4.5 out of 5
Bald Head
Save 100% on your flight
Price was $2,788, price is now $1,924 per person
$1,924
per person
Sep 23 - Sep 28
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9.4/10 Exceptional! (1,006 reviews)

Inn at Diamond Cove

Inn at Diamond Cove

3.5 out of 5
Price was $1,248, price is now $880 per person
$880
per person
Sep 13 - Sep 18
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)
8.8/10 Excellent! (200 reviews)
Friendly staff, went above and beyond.

Reviewed on Jul 20, 2026

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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

4 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.
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

$77
per adult
88% of travellers recommend
Sunset Windjammer Cruise Along the Coast of Portland Maine
Portland Lighthouse Boat Cruise with Oysters & Prosecco

Portland Explorer: Boat Cruise with Oysters & Prosecco

$137
per adult
Portland Explorer: Boat Cruise with Oysters & Prosecco
Portland, Maine: Sightseeing Trolley Tour with a Guide

Portland, Maine: 60-Minute Narrated Sightseeing Trolley Tour

$41
per adult
100% of travellers recommend
Portland, Maine: 60-Minute Narrated Sightseeing Trolley Tour
See all activities in Portland

Portland Hotel Deals

Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

3 out of 5
81 Riverside St Portland ME
Fully refundableReserve now, pay when you stay
$145 nightly
The price is $160 total per night from Jul 27 to Jul 28
$160 total
Jul 27 - Jul 28
Total with taxes and fees
Fireside Inn & Suites Portland
La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

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

3 out of 5
340 Park Ave Portland ME
Fully refundableReserve now, pay when you stay
$179 nightly
The price is $198 total per night from Jul 26 to Jul 27
$198 total
Jul 26 - Jul 27
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Portland DT/Maine Med
Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
Fully refundable
$144 nightly
The price is $159 total per night from Aug 2 to Aug 3
$159 total
Aug 2 - Aug 3
Total with taxes and fees
Clarion Hotel Portland Airport ME
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 $638 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.