Cumberland Holidays

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    Better together
    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place

Top hotels in Cumberland

Rocky Gap Casino & Resort
Rocky Gap Casino & Resort
3 out of 5
16701 Lakeview Road NE, Cumberland, MD
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (1,196 reviews)
"Great property. We will be back in winter great views!= Great pictures"

Reviewed on 15 Jun, 2025

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Rocky Gap Casino & Resort
Ramada by Wyndham Cumberland Downtown
Ramada by Wyndham Cumberland Downtown
3 out of 5
100 South George Street, Cumberland, MD
Fully refundableReserve now, pay when you stay
The price is S$125 per night from 1 Jul to 2 Jul
S$125
1 Jul - 2 Jul
includes taxes & fees
6.8/10 (1,005 reviews)
"Very clean every time I stay there"

Reviewed on 15 Jun, 2025

Ramada by Wyndham Cumberland Downtown
Sleep Inn & Suites Cumberland - LaVale
Sleep Inn & Suites Cumberland - LaVale
2.5 out of 5
13320 Ali Ghan Road NE, Cumberland, MD
Fully refundableReserve now, pay when you stay
The price is S$154 per night from 3 Jul to 4 Jul
S$154
3 Jul - 4 Jul
includes taxes & fees
9.2/10 Wonderful! (1,002 reviews)
"A good place for an affordable price"

Reviewed on 9 Jun, 2025

Sleep Inn & Suites Cumberland - LaVale
See all 2,630 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.

Frequently asked questions

How much does a Cumberland holiday package cost?
You'll find cheap prices on Expedia for your Cumberland break. However, factors like the season, choice of hotel and length of stay will determine how much your holiday to Cumberland costs.
What are the cheapest months to go to Cumberland?
If you're hoping to book a cheap Cumberland holiday package, consider travelling in January, February and March. You'll usually find better rates on hotels and airfares during these months --- ideal for budget-conscious travellers.
How many days is enough for Cumberland?
We recommend planning a Cumberland holiday for a minimum of 2 days. This gives you enough time to check off top sights such as F. Brooke Whiting House and Museum and Gilchrist Gallery, as well as check out neighbourhoods like Bowmans Addition and Mount Savage Junction. You might even be able to fit in a day trip outside of Cumberland.
Is it worth booking a holiday package to Cumberland?
Whether you want to check out top sights such as Downtown Cumberland Historic District and C&O Canal National Historic Park Visitor's Centre on your Cumberland holiday, or coming for its excellent nature, history and culture, there's something for everyone here. With so much to experience, you'll soon find out why so many families think Cumberland is a good holiday destination.
How to find the best Cumberland package deals?
Begin your search for a Cumberland package deal by entering your destination and preferred travel dates under our "Packages" tab. Then apply a few filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the ideal Cumberland package deal right away, just switch up your dates and search again. Remember 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 holiday as a package?
You can enjoy significant savings on your next Cumberland getaway by booking a tailored holiday package. Click on the "Package" heading, then enter your travel dates and destination to see some great flight and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a holiday package to Cumberland?
If you're planning a spontaneous Cumberland holiday, check out 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 ahead.
How to plan a trip to Cumberland?

  1. Choose when to go: Check your schedule and get packing. Your favourite season and the type of activities available will also help you decide when to holiday in Cumberland.
  2. Figure out your budget: Ensure you have enough money to cover everything from transportation and meals to airfares and activities. Your hotel will likely be the largest expense during your trip to Cumberland.
  3. Decide your trip length: Think about how much time you want to spend discovering Cumberland. Plan your days so you can get to all the attractions and activities you're interested in at a leisurely pace.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to find a Cumberland holiday package that brings all your bookings together.

Popular places to visit

Downtown Cumberland Historic District

Downtown Cumberland Historic District

Find out about the history of Cumberland when you take a trip to Downtown Cumberland Historic District. Discover the area's mountain views and casinos.

Downtown Cumberland Historic District

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.