Cumberland Trips (flight + hotel)

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Top hotels in Cumberland

The Westin Portland Harborview
The Westin Portland Harborview
4 out of 5
157 High St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is P13,913 per night from Jul 2 to Jul 3
P13,913
P15,624 total
Jul 2 - Jul 3
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
"hotel was great except the air conditioning was not working overnight in our rooms & it was during a heat wave so it wasn't pleasant."

Reviewed on Jun 25, 2025

The Westin Portland Harborview
Hyatt Place Portland Downtown - Old Port Square
Hyatt Place Portland Downtown - Old Port Square
3 out of 5
433 Fore St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is P15,214 per night from Jun 30 to Jul 1
P15,214
P16,833 total
Jun 30 - Jul 1
includes taxes & fees
8.8/10 Excellent! (1,143 reviews)
"The location is perfect for a day in the city. Close to everything. The staff was friendly. The free shuttle to the airport was easy to arrange with the service offered 24 hours. I was transported at 3:20 am to the airport saving the cost of an Uber and assured safety at the hour. The gym was under ..."

Reviewed on Jun 23, 2025

Hyatt Place Portland Downtown - Old Port Square
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 P7,075 per night from Jun 30 to Jul 1
P7,075
P7,712 total
Jun 30 - Jul 1
includes taxes & fees
7.8/10 Good! (1,022 reviews)
"Room was clean and quiet. Many small ants were sharing room just like at home. Loved small fridge and micro in room."

Reviewed on Jun 28, 2025

Days Inn by Wyndham Airport/Maine Mall
See all 1,856 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.

Frequently asked questions

How much does a Cumberland vacation 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 vacation 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 vacation 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 vacation. 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 vacation as a package?
You can enjoy significant savings on your Cumberland retreat by booking a customized vacation package. Check the "Package" heading, then enter your destination and travel dates to view the best hotel and flight prices. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation 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 favorite 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 accommodations and airfare: Once you've settled on your trip dates and duration, book the perfect Cumberland vacation package for you.

What to do in Cumberland

Portland Downtown Highlights: "The Golden Adventure" Exploration Game

Downtown Golden Adventure Quest Experience in Portland

P486
per adult
Downtown Golden Adventure Quest Experience in Portland
Portland Tall Ship Cruise on Casco Bay

Portland Tall Ship Cruise on Casco Bay

P5,644
per adult
84% of travellers recommend
Portland Tall Ship Cruise on Casco Bay
Portland: Schooner Tall Ship Cruise on Casco Bay

Portland: Schooner Tall Ship Cruise on Casco Bay

P6,079
per adult
Portland: Schooner Tall Ship Cruise on Casco Bay
See all activities in Cumberland
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.