Cumberland Holidays

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Cumberland Holiday

Our pick of the best Cumberland Hotel Deals

The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St Portland ME
The price is NZ$478 per night from 30 Aug to 31 Aug
NZ$478
30 Aug - 31 Aug
includes taxes & fees
The Westin Portland Harborview
Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

3 out of 5
81 Riverside St Portland ME
Fully refundableReserve now, pay when you stay
The price is NZ$279 per night from 30 Aug to 31 Aug
NZ$279
30 Aug - 31 Aug
includes taxes & fees
8.2/10 Very good! (1,034 reviews)
"There was mold on the shower curtains and in the tub. The room smell like mold and mothballs."

Reviewed on 31 July 2026

Fireside Inn & Suites Portland
Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
Fully refundable
The price is NZ$286 per night from 11 Aug to 12 Aug
NZ$286
11 Aug - 12 Aug
includes taxes & fees
Clarion Hotel Portland Airport ME
See all 1,908 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.

Stay near popular Cumberland attractions

Greely Center for the Arts

Enjoy an outing to Greely Center for the Arts during your stay in Cumberland.
See properties

What to do in Cumberland

Casco Bay Morning Windjammer Sail

Casco Bay Morning Windjammer Sail

NZ$107
per adult
Casco Bay Morning Windjammer Sail
Portland Lighthouse Boat Cruise with Oysters & Prosecco

Portland Explorer: Boat Cruise with Oysters & Prosecco

NZ$241
per adult
Portland Explorer: Boat Cruise with Oysters & Prosecco
Sunset Windjammer Cruise Along the Coast of Portland Maine

Sunset Windjammer Cruise Along the Coast of Portland Maine

NZ$136
per adult
88% of travellers recommend
Sunset Windjammer Cruise Along the Coast of Portland Maine
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.