Cumberland Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $1,096 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.
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel
Price was CA $1,417, price is now CA $1,151 per person
CA $1,151
per person
Jul 10 - Jul 15
found 16 hours ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
8.4/10 Very Good! (2,891 reviews)
Overall this was a good experience. The staff was friendly and the property was clean.
Reviewed on Apr 14, 2026
Portland Harbor Hotel
Downtown Portland
Price was CA $2,378, price is now CA $1,655 per person
CA $1,655
per person
Jul 10 - Jul 15
found 16 hours ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
9.2/10 Wonderful! (1,766 reviews)
Convenient location and well decorated with excellent dining facility.
staff is charming.
Reviewed on Apr 16, 2026
Portland Regency Hotel & Spa
Downtown Portland
Price was CA $2,240, price is now CA $1,791 per person
CA $1,791
per person
Jul 10 - Jul 15
found 16 hours ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
9.4/10 Exceptional! (1,619 reviews)
Pet friendly and centrally located. A very nice getaway weekend.
Reviewed on Apr 13, 2026
The Docent's Collection at 121 Middle Street
Downtown Portland
Price was CA $3,043, price is now CA $2,488 per person
CA $2,488
per person
Jul 10 - Jul 15
found 16 hours ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
9.6/10 Exceptional! (291 reviews)
We thoroughly enjoyed our 4-night stay at The Docent's Collection. The staff was outstanding (shout-out to Spencer and Sarah!). The apartment we stayed in was roomy, impeccably clean, and well-furnished. We had everything we needed for our stay. Security was great, parking was easy, and right next to a police parking lot, so very secure. We look forward to staying here again!
Reviewed on Apr 15, 2026
Cumberland Hotel Deals
The Westin Portland Harborview
157 High St Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $204 per night from Apr 19 to Apr 20
CA $204
CA $226 total
Apr 19 - Apr 20
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
The staff should tell the gusts that breakfast need voucher even the gusts already paid the breakfast.
Reviewed on Apr 15, 2026
Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $167 per night from Apr 26 to Apr 27
CA $167
CA $237 total
Apr 26 - Apr 27
includes taxes & fees
9.2/10 Wonderful! (1,774 reviews)
Great location!
Reviewed on Apr 17, 2026
HomeAwhile
205 Southborough Drive Scarborough ME
Fully refundableReserve now, pay when you stay
The price is CA $134 per night from Apr 27 to Apr 28
CA $134
CA $146 total
Apr 27 - Apr 28
includes taxes & fees
9.4/10 Exceptional! (22 reviews)
It was a perfect stay!
Reviewed on Apr 8, 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.
What to do in Cumberland
Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour
CA $13
per traveller
Ultimate Portland Self-Guided Driving GPS Audio Tour
CA $23
per traveller
100% of travellers recommend
Portland Smartphone Audio Tour: Self-Guided Drive
CA $21
per traveller
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
