Cumberland Vacations from $932
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Your Cumberland Vacation
Say bye-bye to planning hassles and hello to a Cumberland vacation package. With everything organized before you go, you can focus on discovering this city, starting with Parkside, which is good for festivals, markets and walking. Not sure what to do or see first during your trip to Cumberland? Don't miss well-known attractions such as Twin Brook Recreation Area. Expedia can help you escape the everyday. Tailor your vacation to Cumberland to suit your style of travel, whatever that may be.
The Latest Cumberland vacation packages
Price found within the past 48 hours. Click for updated prices.
The Docent's Collection at 178 Middle Street
Downtown Portland
$1,039
per person
Dec 3 - Dec 8
found 15 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
9.6/10 Exceptional! (61 reviews)
Amazing rooms amazing staff perfect location absolutely amazing !!!! Can’t wait to
Go back
Reviewed on Sep 27, 2026
The Docent's Collection at 121 Middle Street
Downtown Portland
$973
per person
Dec 3 - Dec 8
found 15 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
9.6/10 Exceptional! (382 reviews)
We have stayed in this Docents Collections building in the recent past and this room did not live up to our expectations. I thought I had booked a two-bedroom with two bathrooms. Perhaps because I inadvertently got onto Expedia's site and also due to booking fairly last minute, we ended up with a corner room with one bath not attached to either of the two bedrooms, and windows that faced a close by brick wall and parking garage. We encourage Docents Collection to invest in a few more amenities for this unit, including waste bins in the bedrooms and more than one pillow and throw in the sitting area.
The location is great and the staff is friendly and accommodating.
Reviewed on Sep 27, 2026
Cliff House Maine
Bald Head
$1,171
per person
Dec 17 - Dec 20
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Portland (PWM)
9.4/10 Exceptional! (1,004 reviews)
It is a perfect place to stay
I can’t think of anything I did not like can’t wait to visit again
Reviewed on Sep 27, 2026
Stay near popular Cumberland attractions
Greely Center for the Arts
Enjoy an outing to Greely Center for the Arts during your stay in Cumberland.
What to do in Cumberland
The Real Portland Tour: City and 3 Lighthouses Historical Tour with a Real Local
$74
per adult
100% of travellers recommend
Sunset Windjammer Cruise Along the Coast of Portland Maine
$77
per adult
90% of travellers recommend
Portland: Casco Bay Morning Lighthouse Cruise
$59
per adult
80% of travellers recommend
Cumberland Hotel Deals
Quality Inn & Suites South Portland
738 Main Street South Portland ME
Fully refundable
$82 nightly
$90 total
Oct 25 - Oct 26
Total with taxes and fees
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel
80 John Roberts Rd. South Portland ME
Fully refundable
$84 nightly
$92 total
Oct 25 - Oct 26
Total with taxes and fees
8.4/10 Very Good! (3,011 reviews)
"Nice location about 15 minutes outside of the main hub. Solid breakfast, price, and place to stay."
Reviewed on Sep 28, 2026
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundableReserve now, pay when you stay
$93 nightly
$103 total
Oct 25 - Oct 26
Total with taxes and fees
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 Cumberland Vacation Packages
Cumberland Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Portland Intl. Jetport Airport (PWM) |
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Frequently asked questions
How much does a Cumberland vacation package cost?
You'll find cheap prices from $932 on Expedia for your Cumberland escape. However, a range of factors like the hotel choice, length of stay and season will determine how much your vacation to Cumberland costs.
What are the cheapest months to go to Cumberland?
If you'd like to book a cheap Cumberland vacation package, consider visiting in November, December and January. You'll generally find better prices on airfares and hotels during these months — perfect for travelers wishing to save money.
How many days is enough for Cumberland?
The ideal duration of your Cumberland vacation depends on what you'd like to see and do. Typically, a handful of days to a week will give you enough time to visit all the major sights and explore some hidden treasures along the way.
How to find the best Cumberland package deals?
Begin your search for a Cumberland package deal by entering your destination and preferred trip dates under our "Packages" tab. Then select some filters, like "Guest rating" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the ideal Cumberland package deal straight away, simply tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Cumberland getaway off to a flying start.
Is it cheaper to book a Cumberland vacation as a package?
You can enjoy significant savings on your Cumberland retreat by booking a customized vacation package. Check the "Package" heading, then enter your destination and travel dates to view the best hotel and flight prices. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Cumberland?
If you're considering a spur-of-the-moment Cumberland adventure, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can find incredible deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Cumberland vacation packages?
Set off on your dream getaway to Cumberland with Expedia's Book Now, Pay Later vacations. There's no need to scrimp and save or wait until the next payday — we've teamed up with online lender Affirm to offer you financial flexibility. Our vacation packages with payment plans mean you can spread the cost across 3, 6 or 12 months. With no hidden or late payment fees, it's easy to budget for your trip 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.
