Cumberland Vacation Packages
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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.
Ramada by Wyndham Saco/Old Orchard Beach Area
Price was CA $1,034, price is now CA $746 per person
CA $746
per person
May 31 - Jun 6
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
7.6/10 Good! (1,049 reviews)
We were just there for one night to visit family nearby. Everyone was friendly and the room was clean and fresh. Beds were comfortable. Great coffee down stairs for this early riser and lots of choices for breakfast.
Reviewed on Mar 22, 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 1 day ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
9.2/10 Wonderful! (1,766 reviews)
The location was very good because you can walk to everything you need in the area. The only thing we didn’t like was the automatic $35 fee you can use toward meals etc in their restaurant, but if you don’t use it you get charged the fee anyway. We felt like it was a way to force us to eat in their restaurant.
Reviewed on Apr 17, 2026
Comfort Inn & Suites Scarborough - Portland
Price was CA $970, price is now CA $759 per person
CA $759
per person
May 31 - Jun 6
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
7/10 Good! (868 reviews)
Was as expected for a cheap hotel. Good enough for a night or two
Reviewed on Apr 14, 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 1 day ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
9.4/10 Exceptional! (1,619 reviews)
Great location, staff was very helpful and accommodating. Restaurants were very good and great service. Very comfortable bed! We found many hidden gems in Old Port on foot. So much to see and do. They do a great job at the Regency. So much history and they are still keeping up with the big boys. This place is special.
Reviewed on Apr 17, 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! (1,002 reviews)
A fine location with nice rooms and helpful staff. The bar on the 15th floor has a nice view of the harbor and pretty good draft beer. Don't order food - or at least the tots as the serving size is meager and quality very low. Not to mention the high cost. Like many cities, Portland does struggle ...
Reviewed on Apr 17, 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! (1,757 reviews)
The location was very good because you can walk to everything you need in the area. The only thing we didn’t like was the automatic $35 fee you can use toward meals etc in their restaurant, but if you don’t use it you get charged the fee anyway. We felt like it was a way to force us to eat in their ...
Reviewed on Apr 17, 2026
HomeAwhile
205 Southborough Drive Scarborough ME
Fully refundableReserve now, pay when you stay
The price is CA $157 per night from Apr 27 to Apr 28
CA $157
CA $172 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
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
