Cumberland Holidays

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Your Cumberland Holiday

With plenty of highlights as well as hidden gems, this city is best explored with a Cumberland holiday package. Check out hotels located in Parkside, which is great for festivals, markets and walking. Twin Brook Recreation Area is just one of the top attractions to check off your to-do list during a trip to Cumberland. Expedia will help you escape your routine. Tailor your holiday to Cumberland to suit your style of travel, whatever that may be!

Cumberland Holiday

Cumberland Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Portland Intl. Jetport Airport (PWM)
Max Temp Winter
-1.11ºC
Max Temp Summer
24ºC

Our pick of the best Cumberland Hotel Deals

Days Inn by Wyndham Airport/Maine Mall

Days Inn by Wyndham Airport/Maine Mall

2 out of 5
461 Maine Mall Rd, South Portland, ME
Fully refundableReserve now, pay when you stay
The price is AU$180 per night from 26 Aug to 27 Aug
AU$180
26 Aug - 27 Aug
includes taxes & fees
7.8/10 Good! (1,229 reviews)
"The room was surprisingly really nice. I think it was recently renovated. They had s decent continental breakfast. My only issue is they allow dogs and dogs bark if they are alone. I wish they would separate the dog owners from the rest of the people so they can keep each other up with their barking. ..."

Reviewed on 23 Aug. 2025

Days Inn by Wyndham Airport/Maine Mall
Clarion Hotel Portland

Clarion Hotel Portland

2.5 out of 5
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is AU$259 per night from 26 Aug to 27 Aug
AU$259
26 Aug - 27 Aug
includes taxes & fees
7.8/10 Good! (1,007 reviews)
"Large hotel with lots of rooms and parking. Close to downtown Portland and easy highway access. The hotel is no thrills but is clean, safe, convenient, and has an impressive indoor pool!"

Reviewed on 22 Aug. 2025

Clarion Hotel Portland
Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
155 Riverside St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is AU$217 per night from 2 Sept to 3 Sept
AU$217
2 Sept - 3 Sept
includes taxes & fees
7.8/10 Good! (1,045 reviews)
"Property is good . Nice area and convenient"

Reviewed on 22 Aug. 2025

Ramada Plaza by Wyndham Portland
See all 1,822 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

What to do in Cumberland

Afternoon Windjammer Cruise Along the Coast of Portland Maine

Afternoon Windjammer Cruise Along the Coast of Portland Maine

AU$103
per adult
Afternoon Windjammer Cruise Along the Coast of Portland Maine
Sunset Lighthouse Cruise Tour from Casco Bay

Sunset Lighthouse Cruise Tour from Casco Bay

AU$90
per adult
90% of travellers recommend
Sunset Lighthouse Cruise Tour from Casco Bay
Harbor Lights and Sights Cruise

Harbor Lights and Sights Cruise

AU$86
per adult
86% of travellers recommend
Harbor Lights and Sights Cruise
See all activities in Cumberland

Frequently asked questions

How much does a Cumberland holiday package cost?
You'll find cheap prices 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 holiday to Cumberland costs.
What are the cheapest months to go to Cumberland?
The off-season is the best time to head to Cumberland if you're on a budget. Another tip for scoring cheap Cumberland holiday packages? Try to avoid public holidays and any major festivals.
How many days is enough for Cumberland?
Usually, a handful of days is enough to see the main attractions during your Cumberland holiday. However, if you'd like to have time to kick back or take day trips, think about extending your itinerary.
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 holiday as a package?
You can enjoy significant savings on your Cumberland retreat by booking a customised holiday package. Check the "Package" heading, then enter your destination and travel dates to view the best hotel and flight prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a holiday 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.
How to plan a trip to Cumberland?

  1. Choose when to travel: Check your schedule and pack your bags. Your favourite season and the type of activities on offer will also help you decide when to escape to Cumberland.
  2. Budget wisely: On top of the cost of your stay, you'll need to consider other expenses. These include transportation, flights and food. Also, set aside a little extra for unexpected costs that could crop up during your trip to Cumberland.
  3. Set the duration of your trip: Start by listing all the attractions and activities you want to get to in Cumberland. Then, estimate how long you'll need for each, as well as any travel time.
  4. Combine your accommodation and airfare: Once you've settled on your trip dates and duration, book the perfect Cumberland holiday package for you.

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