Cumberland Vacations from $323

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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.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $455, price is now $323 per person
$323
per person
Jan 5 - Jan 8
found 13 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9.2/10 Wonderful! (1,668 reviews)
We were only here 1 night, but our room was clean and cozy. We walked right down the street for dinner at $3 Deweys and had a great time! We used our destination fee credit to have breakfast delivered and were thourouly dissapointed. I took one bite and knew something was not right, the potatoes were fried in rancid grease and inedibile. My husband had an omlet that was at least edibile but nothing special.

Reviewed on Nov 24, 2025

The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $654, price is now $388 per person
$388
per person
Jan 5 - Jan 8
found 13 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9.8/10 Exceptional! (86 reviews)
Loved this place and would definitely stay here next time we go back.

Reviewed on Oct 15, 2025

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Save 100% on your flight
Price was $709, price is now $469 per person
$469
per person
Jan 5 - Jan 8
found 13 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9.6/10 Exceptional! (161 reviews)
The property is beautiful, the staff is kind, and the rooms are spacious and clean. It was great to have a safe place to park the car while having so many things to do within walking distance. Being able to grab a quick breakfast before heading out was great too! We loved our stay here!

Reviewed on Nov 23, 2025

The Docent's Collection - Boyd Block

The Docent's Collection - Boyd Block

2 out of 5
Downtown Portland
Price was $556, price is now $406 per person
$406
per person
Jan 5 - Jan 8
found 13 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
10/10 Exceptional! (2 reviews)
Really nice and clean new hotel!

Reviewed on Oct 27, 2025

Inn By The Sea

Inn By The Sea

4 out of 5
Save 100% on your flight
Price was $1,240, price is now $914 per person
$914
per person
Jan 5 - Jan 8
found 13 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9.4/10 Exceptional! (288 reviews)
Room was ready early friendly staff and room is better than expected

Reviewed on Nov 16, 2025

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Discover the most popular places to visit in Cumberland

Twin Brook Recreation Area

Explore the great outdoors at Twin Brook Recreation Area, a lovely green space in Cumberland Center. Stroll along the area's waterfront, or simply savor its top-notch restaurants.

Twin Brook Recreation Area

What to do in Cumberland

Portland Self-Guided Driving Audio Tour

Portland Smartphone Audio Tour: Self-Guided Drive

$17
per traveler
Portland Smartphone Audio Tour: Self-Guided Drive
Tour of Palace & Monument of Marrakech

Tour of Palace & Monument of Marrakech

$39
per adult
Tour of Palace & Monument of Marrakech
Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour

Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour

$10
per traveler
Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour
See all activities in Cumberland

Cumberland Hotel Deals

Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $93 total per night from Nov 30 to Dec 1
$93 total
Nov 30 - Dec 1
Total with taxes and fees
7.8/10 Good! (1,251 reviews)
Yes we loved room 511 with the pull out bed chair !

Reviewed on Nov 19, 2025

Clarion Hotel Portland Airport ME
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $154 total per night from Nov 30 to Dec 1
$154 total
Nov 30 - Dec 1
Total with taxes and fees
9.2/10 Wonderful! (1,686 reviews)
We were only here 1 night, but our room was clean and cozy. We walked right down the street for dinner at $3 Deweys and had a great time! We used our destination fee credit to have breakfast delivered and were thourouly dissapointed. I took one bite and knew something was not right, the potatoes ...

Reviewed on Nov 24, 2025

Portland Harbor Hotel
DoubleTree by Hilton Hotel Portland

DoubleTree by Hilton Hotel Portland

4 out of 5
363 Maine Mall Rd South Portland ME
Fully refundableReserve now, pay when you stay
$74 nightly
The price is $81 total per night from Dec 4 to Dec 5
$81 total
Dec 4 - Dec 5
Total with taxes and fees
7.8/10 Good! (1,313 reviews)
The bathroom needed more cleaning. Baseboards hadn’t been dusted in a long time, looked like mold around sink and bath tub was very slippery.

Reviewed on Nov 22, 2025

DoubleTree by Hilton Hotel Portland
See all 1,793 properties in Cumberland
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 $323 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.