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.
InnSeason Resorts The Falls at Ogunquit
Price was CA $1,610, price is now CA $1,277 per person
CA $1,277
per person
Oct 11 - Oct 18
found 8 hours ago
Roundtrip flight included
Regina (YQR) to Portland (PWM)
9.4/10 Exceptional! (346 reviews)
Clean comfortable rooms. Nice amenities, walking distance to the beach and restaurants. Short drive or shuttle to downtown area.
We would return and recommend this place.
Reviewed on Aug 16, 2025
USA Inn
Price was CA $909, price is now CA $771 per person
CA $771
per person
Oct 11 - Oct 18
found 8 hours ago
Roundtrip flight included
Regina (YQR) to Portland (PWM)
8/10 Very Good! (699 reviews)
WiFi was iffy but besides that great place to stay. Staff were great, about 20 min walk from the beach. Good restaurants surrounding.
Reviewed on Sep 7, 2025
Old Orchard Beach Inn
Price was CA $1,437, price is now CA $1,252 per person
CA $1,252
per person
Oct 11 - Oct 18
found 8 hours ago
Roundtrip flight included
Regina (YQR) to Portland (PWM)
8.4/10 Very Good! (1,004 reviews)
Beds were comfortable and the rooms were clean.
Quirky old hotel with character. However, there were issues with the windows and difficulty/failure to close them.
Decoration was shabby. We had to report a safety issue as one of the beds had metal sticking out from the end which was a hazard in the room and caused a nasty fall for one of our party.
Breakfast didn't start until 8.30 which we considered was too latealthough we had been informed that it started at 8.
Overall a very mediocre experience.
Reviewed on Sep 9, 2025
Cumberland Hotel Deals
Fireside Inn & Suites Portland
81 Riverside St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $168 per night from Oct 7 to Oct 8
CA $168
CA $186 total
Oct 7 - Oct 8
includes taxes & fees
Clarion Hotel Portland
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $163 per night from Sep 15 to Sep 16
CA $163
CA $180 total
Sep 15 - Sep 16
includes taxes & fees
La Quinta Inn & Suites by Wyndham Portland DT/Maine Med
340 Park Ave, Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $247 per night from Sep 21 to Sep 22
CA $247
CA $273 total
Sep 21 - Sep 22
includes taxes & fees
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
Afternoon Windjammer Cruise Along the Coast of Portland Maine
CA $92
per adult
80% of travellers recommend
Portland: Sightseeing Cruise to Portland Head Light
CA $56
per adult
98% of travellers recommend
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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.
