Cumberland Packages (Flight + Hotel)

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Top hotels in Cumberland

Clarion Pointe South Portland

Clarion Pointe South Portland

2 out of 5
675 Main Street I-95 South Portland ME
Fully refundable
The price is ฿3,066 per night from 6 Sept to 7 Sept
฿3,066
฿3,342 total
6 Sept - 7 Sept
includes taxes & fees
7.4/10 Good! (640 reviews)
"They canceled my booking, which was pre paid when are flight was delayed by 70 without notice. I did not find out until we tried to check in."

Reviewed on 6 Aug 2026

Clarion Pointe South 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 ฿4,465 per night from 2 Sept to 3 Sept
฿4,465
฿4,940 total
2 Sept - 3 Sept
includes taxes & fees
8.2/10 Very good! (1,609 reviews)
"We were there for a short time. We had no complaints."

Reviewed on 6 Aug 2026

Clarion Hotel Portland Airport ME
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
The price is ฿8,410 per night from 30 Aug to 31 Aug
฿8,410
฿9,305 total
30 Aug - 31 Aug
includes taxes & fees
Portland Regency Hotel & Spa
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

Sunset Windjammer Cruise Along the Coast of Portland Maine

Sunset Windjammer Cruise Along the Coast of Portland Maine

฿2,577
per adult
90% of travellers recommend
Sunset Windjammer Cruise Along the Coast of Portland Maine
Portland Maine Self-Guided Driving & Walking Audio Tour Bundle

Portland Maine Self-Guided Driving & Walking Audio Tour Bundle

฿753
per adult
90% of travellers recommend
Portland Maine Self-Guided Driving & Walking Audio Tour Bundle
Portland, Maine: Sightseeing Trolley Tour with a Guide

Portland, Maine: 60-Minute Narrated Sightseeing Trolley Tour

฿1,347
per adult
100% of travellers recommend
Portland, Maine: 60-Minute Narrated Sightseeing Trolley Tour
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.