Cumberland Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Cumberland Vacation
Say bye-bye to planning hassles and hello to a Cumberland vacation package. With everything organized before you go, you can focus on discovering this city, starting with Parkside, which is good for festivals, markets and walking. Not sure what to do or see first during your trip to Cumberland? Don't miss well-known attractions such as Twin Brook Recreation Area. Expedia can help you escape the everyday. Tailor your vacation to Cumberland to suit your style of travel, whatever that may be.
Top Cumberland Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Docent's Collection at 121 Middle Street
Downtown Portland
CA $1,958
per person
Oct 19 - Oct 23
found 8 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Portland (PWM)
9.6/10 Exceptional! (382 reviews)
Other than being a little hard to find, this spot was wonderful and so much nicer than a hotel room! Great location.
Reviewed on Sep 18, 2026
The Docent's Collection at 178 Middle Street
Downtown Portland
CA $1,858
per person
Oct 19 - Oct 23
found 8 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Portland (PWM)
9.6/10 Exceptional! (61 reviews)
Staff was very very good and super quick to respond.. I really liked the location for my visit bc everything was easily walkable. Room was comfortable but a little interesting walking all the way across for bathroom. A few small glitches with electrical probably just bc it’s done recently renovated.
Reviewed on Sep 18, 2026
Blind Tiger Portland - Danforth Street.
West End
CA $2,651
per person
Oct 19 - Oct 23
found 8 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Portland (PWM)
9.6/10 Exceptional! (192 reviews)
Place was charming and quirky. Very comfortable and well located.
Reviewed on Sep 18, 2026
Ready to book your vacation to Cumberland?
Cumberland Hotel Deals
Quality Inn & Suites South Portland
738 Main Street South Portland ME
Fully refundable
CA $123
CA $134 total
Oct 18 - Oct 19
includes taxes & fees
6.4/10 (1,133 reviews)
"It was barely acceptable. Tun looked dirty and the main door showed signs of damage. The door to connecting room could not be deadbolt locked. Two flimsy back up locks were able to be engaged."
Reviewed on Sep 18, 2026
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel
80 John Roberts Rd. South Portland ME
Fully refundable
CA $153
CA $167 total
Oct 20 - Oct 21
includes taxes & fees
8.4/10 Very good! (3,003 reviews)
"The staff at the front desk checked us in and out efficiently but lacked the warmth and hospitality. The bathroom stall was also slippery. Almost fell. Need to put some kind of traction to prevent falls."
Reviewed on Sep 18, 2026
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundableReserve now, pay when you stay
CA $151
CA $167 total
Oct 18 - Oct 19
includes taxes & fees
8.2/10 Very good! (1,700 reviews)
"There was an odor to the second floor hallways and my room. The bed was not very comfortable. It was very inexpensive, and the room was clean looking, but the smell was off putting."
Reviewed on Sep 18, 2026
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.
What to do in Cumberland
Sunset Windjammer Cruise Along the Coast of Portland Maine
CA $107
per adult
90% of travellers recommend
Portland: Casco Bay Morning Lighthouse Cruise
CA $82
per adult
Frequently asked questions
How much does a Cumberland vacation package cost?
You can snap up a vacation package to this top destination from CA $1,661 on Expedia. But how much your vacation to Cumberland costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Cumberland?
To score cheap Cumberland vacation packages, plan your getaway outside of peak times such as school holidays. You'll generally find lower prices and better availability when it's less busy.
How many days is enough for Cumberland?
Usually, a handful of days is enough to check out the top attractions during your Cumberland vacation. But if you prefer to have some time to kick back or take day tours, think about extending your itinerary.
How to find the best Cumberland package deals?
Finding a cheap Cumberland package deal is a cinch with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your budget range, add a few filters and see what's available. You can tailor your search by "Amenities," "Property type," "Traveller experience" and more. Order the results by "Price: low to high" to discover the most pocket-friendly Cumberland package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are often lower.
Is it cheaper to book a Cumberland vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging hotels and flights individually. Better still, you can customize your Cumberland trip to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Cumberland?
Enjoy fantastic discounts by reserving your flights in advance with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for a spur-of-the-moment Cumberland vacation.
How to plan a trip to Cumberland?
- Pick your dates: What you want to do in Cumberland and your favourite season will help you decide when to travel.
- Calculate your budget: Ensure you have enough money to pay for everything from food and transportation to airfares and activities. Your accommodations will probably be the biggest expense during your trip to Cumberland.
- Determine how many days away: Start by compiling a list of the sights and activities you want to get to in Cumberland. Then, estimate how long you'll need at each, as well as any travel time.
- Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to find a Cumberland vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
