Cumberland Holidays

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Top hotels in Cumberland

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 S$208 per night from 20 Jul to 21 Jul
S$208
20 Jul - 21 Jul
includes taxes & fees
7.8/10 Good! (1,027 reviews)
"The Jamaican lady at the desk was very helpful"

Reviewed on 14 Jul, 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 S$216 per night from 20 Jul to 21 Jul
S$216
20 Jul - 21 Jul
includes taxes & fees
7.8/10 Good! (1,028 reviews)
"Staff welcoming, friendly and very helpful in providing the various types of eateries nearby. The shuttle bus on call when needed. I enjoyed my stay at the Clarion. Hotel is right near the Portland Transportation Center (literally located back door--walkable)"

Reviewed on 15 Jul, 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 S$220 per night from 22 Jul to 23 Jul
S$220
22 Jul - 23 Jul
includes taxes & fees
7.6/10 Good! (1,033 reviews)
Good and clean
"Good location for us and very convenient to all the areas nearby that we had to go. We enjoyed the quiet and were able to easily and quickly get additional towels and supplies as we needed."

Reviewed on 14 Jul, 2025

Ramada Plaza by Wyndham Portland
See all 1,863 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.

What to do in Cumberland

Portland Downtown Highlights: "The Golden Adventure" Exploration Game

Downtown Golden Adventure Quest Experience in Portland

S$11
per adult
Downtown Golden Adventure Quest Experience in Portland
Afternoon Windjammer Cruise Along the Coast of Portland Maine

Afternoon Windjammer Cruise Along the Coast of Portland Maine

S$86
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

S$72
per adult
90% of travellers recommend
Sunset Lighthouse Cruise Tour from Casco Bay
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. 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.