Cumberland Vacations from $348

Book a Hotel + Flight or Car together to unlock savings

Your Cumberland Vacation

When you choose a Cumberland vacation package, you can relax and enjoy your adventure to the fullest. Uncover the best things about this vibrant city knowing that everything has been organized in advance. Levoy Theater, Wheaton Village and Riverfront Renaissance Center for the Arts are just a few of the attractions worth exploring during your trip to Cumberland. Whoever you're escaping with and whatever the size of your budget, your ultimate Cumberland vacation is just a few clicks away with Expedia.

The Latest Cumberland Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Dec 10 - Dec 13

    Tropicana Atlantic City – A Caesars Rewards Destination + Flight

    Chelsea
    3 nights
    3.5 star property
    7.6/10 - Good (17,375 reviews)
    "I checked my wheelchair into the Bell Captain Desk and rented a electric wheelchair. When I returned the electric chair they returned a broken chair and refuse to do anything to correct"
    Reviewed November 7, 2026
    Roundtrip • Atlanta (ATL) - Atlantic City (ACY)
    ATL - PHL • Nonstop PHL - ATL • Nonstop
    Save 100% on your flight
    $586
    $348
    per traveler
    found 1 day ago
    Tropicana Atlantic City – A Caesars Rewards Destination
  • Jan 8 - Jan 10

    Casa De Miliki + Flight

    South Philadelphia
    2 nights
    3.0 star property
    Roundtrip • Atlanta (ATL) - Philadelphia (PHL)
    ATL - PHL • Nonstop PHL - ATL • Nonstop
    $3,612
    $1,961
    per traveler
    found 1 day ago
    Casa De Miliki
  • Dec 10 - Dec 13

    Harrah’s Resort Atlantic City Hotel & Casino – A Caesars Rewards Destination + Flight

    Midtown North
    3 nights
    4.0 star property
    7.8/10 - Good (14,296 reviews)
    Roundtrip • Atlanta (ATL) - Atlantic City (ACY)
    ATL - PHL • Nonstop PHL - ATL • Nonstop
    Save 100% on your flight
    $651
    $354
    per traveler
    found 1 day ago
    Harrah’s Resort Atlantic City Hotel & Casino – A Caesars Rewards Destination
  • Jan 8 - Jan 10

    Cozy Home near City Center with Hot tub + Flight

    South Philadelphia
    2 nights
    3.0 star property
    10/10 - Exceptional (3 reviews)
    "This was the perfect place for my group and our needs. Enough beds with options; a dark, quiet room in the basement, a shared room with a two full beds, the top floor king size suite, even a pull out sofa! All useful accommodations for a party of 5 or more. To top it off, the roof top hot tub with a city skyline view was incredible! It was a great location too, in walking distance to our venue in South Philly. Everything worked out perfectly, and I'm grateful that this option was available...."
    Reviewed March 2, 2026
    Roundtrip • Atlanta (ATL) - Philadelphia (PHL)
    ATL - PHL • Nonstop PHL - ATL • Nonstop
    $3,538
    $2,038
    per traveler
    found 1 day ago
    Cozy Home near City Center with Hot tub
  • Dec 11 - Dec 13

    New Season Royals + Flight

    Chester
    2 nights
    2.0 star property
    9.2/10 - Wonderful (159 reviews)
    Roundtrip • Orlando (MCO) - Philadelphia (PHL)
    MCO - PHL • Nonstop PHL - MCO • 1 stop
    $574
    $364
    per traveler
    found 1 day ago
    New Season Royals

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 $348 on Expedia for your Cumberland break. 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?

December, January and February are the best times to search for cheap Cumberland vacation packages. Traveling in quieter months means you can generally find better prices on flights and hotels.

How many days is enough for Cumberland?

Typically, a handful of days is enough to explore the top sights during your Cumberland vacation. But if you prefer to have time to relax or take day tours, think about extending your itinerary.

How to find the best Cumberland package deals?

Start your search for a Cumberland package deal by entering your destination and preferred trip dates under our "Packages" tab. Then add a few filters, like "Guest rating" and "Property type," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the perfect Cumberland package deal right away, just play around with your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Cumberland adventure off to a flying start.

Is it cheaper to book a Cumberland vacation as a package?

An Expedia vacation package could land you great savings when compared to booking flights and accommodations separately. Better still, you can personalize your Cumberland trip to fit your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.

When to book a vacation package to Cumberland?

If you're considering a spur-of-the-moment Cumberland vacation, browse our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can land amazing deals on your hotels and flights by booking well in advance.

How to plan a trip to Cumberland?

  1. Pick the perfect time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to travel to Cumberland.
  2. Set your budget: Factor in costs like flights, food and transportation when calculating how much to set aside for your trip to Cumberland. Then, choose a hotel that matches your budget, whether that's a wallet-friendly stay or a lavish getaway.
  3. Organize your Cumberland escape with our trip planning tool: Look for and book stays and experiences all in one place. You can also collaborate with your group to plan an unforgettable trip to Cumberland together.
  4. Decide how long to go for: Now that you're up to speed on Cumberland, you can figure out the ideal length of your break. Put together a draft itinerary and allocate enough time to cover everything you want to see.
  5. Combine your airfare and accommodations: After you've settled on your trip dates and duration, lock in the ideal Cumberland vacation package for you.
  6. Book activities and experiences ahead of time: Whether it's entrance to a big attraction or a day trip, you won't have to worry about missing out on Cumberland's highlights. Find all the exciting things to do in Cumberland with our dedicated activity guide.

Does Expedia offer Book Now, Pay Later Cumberland vacation packages?

Your Cumberland getaway is meant to be an escape from your daily routine, not a reason for money-related stress. So to allow you extra flexibility, we've teamed up with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.