Cumberland Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, 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.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was CA $1,381, price is now CA $1,155 per person
CA $1,155
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.2/10 Wonderful! (1,851 reviews)
Great location and spacious rooms. We brought our dog too! Loved grabbing a pre dinner drink and sitting by the cozy fireplace.

Reviewed on Nov 4, 2026

The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

3.5 out of 5
Downtown Portland
Price was CA $2,111, price is now CA $1,578 per person
CA $1,578
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.6/10 Exceptional! (419 reviews)

Inn By The Sea

Inn By The Sea

4 out of 5
Price was CA $1,762, price is now CA $1,475 per person
CA $1,475
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.6/10 Exceptional! (342 reviews)

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was CA $2,207, price is now CA $1,934 per person
CA $1,934
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.6/10 Exceptional! (199 reviews)

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Downtown Portland
Price was CA $1,353, price is now CA $1,188 per person
CA $1,188
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.4/10 Exceptional! (1,780 reviews)
Staff at the reception was not very warm and friendly at both check in and check out. However the valet staff and lounge staff were very kind and hospitable.

Reviewed on Nov 4, 2026

Ready to book your vacation to Cumberland?

 

Choose your dates

Cumberland Hotel Deals

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 CA $141 per night from Dec 6 to Dec 7
CA $141
CA $156 total
Dec 6 - Dec 7
includes taxes & fees
9/10 Wonderful! (1,005 reviews)
"Good stay"

Reviewed on Nov 3, 2026

The Westin Portland Harborview
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 CA $113 per night from Nov 16 to Nov 17
CA $113
CA $125 total
Nov 16 - Nov 17
includes taxes & fees
8.2/10 Very good! (1,850 reviews)
"Na"

Reviewed on Nov 5, 2026

Clarion Hotel Portland Airport ME
Quality Inn & Suites South Portland

Quality Inn & Suites South Portland

2.5 out of 5
738 Main Street South Portland ME
Fully refundable
The price is CA $85 per night from Nov 11 to Nov 12
CA $85
CA $92 total
Nov 11 - Nov 12
includes taxes & fees
6.2/10 (1,213 reviews)
"My stay at this hotel was extremely disappointing and frustrating. From the moment I arrived, there were problems. The cable TV was not working, and the Wi-Fi connection was terrible, making it difficult to use the internet."

Reviewed on Nov 4, 2026

Quality Inn & Suites South Portland
See all 1,793 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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

CA $109
per adult
92% of travellers recommend
Sunset Windjammer Cruise Along the Coast of Portland Maine
Portland: Casco Bay Morning Lighthouse Cruise

Portland: Casco Bay Morning Lighthouse Cruise

CA $83
per adult
80% of travellers recommend
Portland: Casco Bay Morning Lighthouse Cruise
Portland, Maine: Hidden Histories Guided Walking Tour

Portland, Maine: Hidden Histories Guided Walking Tour

CA $76
per adult
Portland, Maine: Hidden Histories Guided Walking Tour
See all activities in Cumberland

Frequently asked questions

How much does a Cumberland vacation package cost?
You can snap up a vacation package to this top destination from CA $1,155 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?

  1. Pick your dates: What you want to do in Cumberland and your favourite season will help you decide when to travel.
  2. 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.
  3. 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.
  4. 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.