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.
84 Main
Price was CA $1,408, price is now CA $1,156 per person
CA $1,156
per person
Apr 2 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Portland (PWM)
10/10 Exceptional! (52 reviews)
Very spacious and relaxing. Nice view of Kennebunk quaint ice rink and Main Street. Coffee shop at Street level was a fantastic add! Beds and bedding were comfortable. Will visit again! Nothing lacking with respect to amenities.
Reviewed on Dec 29, 2025
Inn By The Sea
Price was CA $1,646, price is now CA $1,445 per person
CA $1,445
per person
Apr 2 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Portland (PWM)
9.4/10 Exceptional! (288 reviews)
Room was ready early friendly staff and room is better than expected
Reviewed on Nov 16, 2025
Portland Harbor Hotel
Downtown Portland
Price was CA $1,367, price is now CA $1,201 per person
CA $1,201
per person
Apr 2 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Portland (PWM)
9.2/10 Wonderful! (1,668 reviews)
The room was super clean and really comfortable. The staff was very helpful and friendly. Got good recommendations from Pearl. In the morning, we had to wait for hot water because the boiler broke. A very stressful situation for the guy at the desk to handle with all the guests but he was helpful and accurate with time estimates. All around great experience.
Reviewed on Feb 10, 2026
Blind Tiger Portland - Danforth Street.
West End
Price was CA $1,857, price is now CA $1,665 per person
CA $1,665
per person
Apr 2 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Portland (PWM)
9.6/10 Exceptional! (161 reviews)
The whole was cozy!
Well curated style and knowledgeable staff.
Reviewed on Jan 5, 2026
The McKernan Inn
Price was CA $1,389, price is now CA $1,246 per person
CA $1,246
per person
Apr 2 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Portland (PWM)
9/10 Wonderful! (83 reviews)
Gorgeous grounds and venue with a beautiful oceanfront view. Plenty of parking as part of SMCC campus. Short drive to downtown Portland and lots of stores around in South Portland. Very unique experience, would stay again without hesitation!
Reviewed on Dec 27, 2025
Cumberland Hotel Deals
The Westin Portland Harborview
157 High St Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $133 per night from Feb 26 to Feb 27
CA $133
CA $147 total
Feb 26 - Feb 27
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
The room was clean and comfortable. Thr hotel itself was beautiful
Reviewed on Feb 4, 2026
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $104 per night from Feb 19 to Feb 20
CA $104
CA $116 total
Feb 19 - Feb 20
includes taxes & fees
8/10 Very Good! (1,354 reviews)
Was nice
Reviewed on Feb 8, 2026
Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (1,757 reviews)
Really nice room. Tub, separate shower, nice linens.
Reviewed on Feb 7, 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 $14
per traveller
Portland Smartphone Audio Tour: Self-Guided Drive
CA $23
per traveller
Ultimate Portland Self-Guided Driving GPS Audio Tour
CA $23
per traveller
100% 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.
