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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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! (1,253 reviews)
The perfect getaway
"The pillows are so soft like sleeping on a cloud the food was excellent and the alcohol cocktails were very good can’t wait to get back there for another few nights love the casino"

Reviewed on 31 Jul, 2025

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Rocky Gap Casino & Resort
Best Western Braddock Inn

Best Western Braddock Inn

2.5 out of 5
1268 National Hwy, Cumberland, MD
Fully refundableReserve now, pay when you stay
The price is S$118 per night from 10 Aug to 11 Aug
S$118
10 Aug - 11 Aug
includes taxes & fees
7.8/10 Good! (1,001 reviews)
"Second time here.Great again.Will definitely return again."

Reviewed on 27 Jul, 2025

Best Western Braddock Inn
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$118 per night from 10 Aug to 11 Aug
S$118
10 Aug - 11 Aug
includes taxes & fees
6.8/10 (1,008 reviews)
"This hotel is great if you want to be walking distance to dining and shops in the downtown, as well as historic trails and museums. Staff was friendly. Rooms were average- clean. Bathroom was good, vanity was small in the double queen room. There is a train that runs right behind the hotel- was surprised ..."

Reviewed on 3 Aug, 2025

Ramada by Wyndham Cumberland Downtown
See all 2,634 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.

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

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.

* 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.