Cumberland Vacations from $650

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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 $1,000, price is now $650 per person
$650
per person
Apr 1 - Apr 6
found 17 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.2/10 Wonderful! (1,668 reviews)
Reduce noise from patrons near elevator and coffee area on second floor, very loud

Reviewed on Jan 10, 2026

The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Downtown Portland
Price was $1,201, price is now $864 per person
$864
per person
Apr 1 - Apr 6
found 17 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.6/10 Exceptional! (249 reviews)
Room and amenities were great and ease of access to both the room and surrounding businesses is ideal.

Reviewed on Jan 10, 2026

The McKernan Inn

The McKernan Inn

3 out of 5
Price was $1,019, price is now $756 per person
$756
per person
Apr 1 - Apr 6
found 17 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9/10 Wonderful! (83 reviews)
Gorgeous grounds and venue with a beautiful oceanfront view. Plenty of parking as part of SMCC campus. Short drive to downtown Portland and lots of stores around in South Portland. Very unique experience, would stay again without hesitation!

Reviewed on Dec 27, 2025

Cliff House Maine

Cliff House Maine

4.5 out of 5
Bald Head
Price was $1,778, price is now $1,378 per person
$1,378
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.4/10 Exceptional! (1,001 reviews)
Loved the hotel had a great time with a group of friends

Reviewed on Jan 12, 2026

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Downtown Portland
Price was $906, price is now $703 per person
$703
per person
Apr 1 - Apr 6
found 17 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.4/10 Exceptional! (1,512 reviews)
Room is awesome , love the hotel.

Reviewed on Jan 12, 2026

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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

$15
per traveler
Portland Smartphone Audio Tour: Self-Guided Drive
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
Ultimate Portland Self-Guided Driving GPS Audio Tour

Ultimate Portland Self-Guided Driving GPS Audio Tour

$17
per traveler
100% of travellers recommend
Ultimate Portland Self-Guided Driving GPS 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
$78 nightly
The price is $87 total per night from Jan 15 to Jan 16
$87 total
Jan 15 - Jan 16
Total with taxes and fees
8/10 Very Good! (1,322 reviews)
Very nice

Reviewed on Jan 11, 2026

Clarion Hotel Portland Airport ME
The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St Portland ME
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $117 total per night from Feb 4 to Feb 5
$117 total
Feb 4 - Feb 5
Total with taxes and fees
8.8/10 Excellent! (1,008 reviews)
Room was clean and had all amenities.

Reviewed on Jan 6, 2026

The Westin Portland Harborview
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
$138 nightly
The price is $152 total per night from Jan 25 to Jan 26
$152 total
Jan 25 - Jan 26
Total with taxes and fees
9.4/10 Exceptional! (1,573 reviews)
Room is awesome , love the hotel.

Reviewed on Jan 12, 2026

Portland Regency Hotel & Spa
See all 1,783 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 $650 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.