Cumberland Vacations from $1,048

Book a Hotel + Flight or Car together to unlock savings

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.
  • Jan 21 - Jan 24

    Cliff House Maine + Flight

    Bald Head
    3 nights
    4.5 star property
    9.4/10 - Exceptional (1,001 reviews)
    Roundtrip • Atlanta (ATL) - Portland (PWM)
    ATL - BOS • Nonstop BOS - ATL • Nonstop
    $1,210
    $1,048
    per traveler
    found 1 day ago
    Cliff House Maine
  • Dec 31 - Jan 5

    Kennebunkport Captains Collection + Flight

    Kennebunkport
    5 nights
    4.5 star property
    9.6/10 - Exceptional (774 reviews)
    "Amazing place for our Mini Moon! Would definitely recommend"
    Reviewed November 13, 2026
    Roundtrip • Dallas (DFW) - Portland (PWM)
    DAL - BOS • Nonstop BOS - DFW • 1 stop
    $1,486
    $1,202
    per traveler
    found 1 day ago
    Kennebunkport Captains Collection
  • Dec 17 - Dec 23

    Blind Tiger Portland – Carleton Street + Flight

    West End
    6 nights
    3.5 star property
    9.6/10 - Exceptional (138 reviews)
    Roundtrip • Atlanta (ATL) - Portland (PWM)
    ATL - PWM • Nonstop PWM - ATL • 2 stops
    $1,570
    $1,310
    per traveler
    found 1 day ago
    Blind Tiger Portland – Carleton Street
  • Dec 17 - Dec 23

    The Docent's Collection at 121 Middle Street + Flight

    Downtown Portland
    6 nights
    3.5 star property
    9.6/10 - Exceptional (431 reviews)
    "The property was excellent. We stayed in a 1 bedroom loft and it was great. Nice sitting area, fully equipped kitchen, beautiful bathroom and nice size bedroom. It was quiet and comfy, and also walking distance to great restaurants. Highly recommend."
    Reviewed November 12, 2026
    Roundtrip • Atlanta (ATL) - Portland (PWM)
    ATL - PWM • Nonstop PWM - ATL • 2 stops
    $1,598
    $1,379
    per traveler
    found 1 day ago
    The Docent's Collection at 121 Middle Street
  • Dec 17 - Dec 23

    Portland Harbor Hotel + Flight

    Downtown Portland
    6 nights
    4.0 star property
    9.2/10 - Wonderful (1,866 reviews)
    "Old hotel recently updated. Great location in Old Port in walking distance of restaurants and shop. Very helpful staff. Easy valet parking. They charge a resort fee but you get it back as credit to use for breakfast or at the bar. Great outdoor patio area with gas fire pit. Great vibe for adult travelers."
    Reviewed November 14, 2026
    Roundtrip • Atlanta (ATL) - Portland (PWM)
    ATL - PWM • Nonstop PWM - ATL • 2 stops
    $1,236
    $1,085
    per traveler
    found 1 day ago
    Portland Harbor Hotel

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Cumberland Hotel Deals

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.

Frequently Asked Questions

How much does a Cumberland vacation package cost?

You'll find cheap prices from $1,048 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.