Cumberland County Vacation Packages
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Your Cumberland County Vacation
When adventure calls, answer it with a tailor-made vacation package to Cumberland County. Wherever your journey takes you and whatever you have planned, get set to discover a destination with so much to offer. With so many things to explore on a trip to Cumberland County, it can be hard to know where to start. Kick off your journey in Portland at Maine Mall and Thompson's Point — two popular attractions here. Another city to add to your itinerary is Brunswick. Don't miss Maine Street and LL Bean Flagship Store. From the instant you book your Cumberland County vacation to the second you come back home, Expedia will take care of you every step of the way.
Top vacation destinations in Cumberland County
Portland
Top Cumberland County Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Fairmont Copley Plaza, Boston
Back Bay
Price was CA $1,217, price is now CA $854 per person
CA $854
per person
Aug 18 - Aug 21
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9/10 Wonderful! (1,254 reviews)
The staff were all super kind and helpful. I really enjoyed the old school and glam aspect of the hotel but did lead to a few things. For example a gap under the door meant a bright light in the room which hinder sleep, room had slight smell of smoke and sound of water dripping. Great location, safe and clean.
Reviewed on Jul 12, 2026
By the Sea Guests Bed & Breakfast & Suites
Price was CA $2,561, price is now CA $1,539 per person
CA $1,539
per person
Aug 23 - Aug 29
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Boston (BOS)
9.4/10 Exceptional! (195 reviews)
The staff here was so kind and thoughtful. The breakfast was amazing all 3 days and the beach was very quiet and great waterfront. The section we stayed has not been updated like some of the other units but was fine and comfortable. The general location was good and easily walkable to food and drink places. Overall, we enjoyed it and would stay here again for sure.
Reviewed on Jul 12, 2026
Good Hotels Boston
South End
Price was CA $1,674, price is now CA $1,136 per person
CA $1,136
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8/10 Very good! (55 reviews)
This was a very clean and well-looked after property, and the staff went out of their way to check everything was in order.
Reviewed on May 23, 2026
Cumberland County Hotel Deals
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundable
The price is CA $203 per night from Jul 26 to Jul 27
CA $203
CA $225 total
Jul 26 - Jul 27
includes taxes & fees
8.2/10 Very good! (1,551 reviews)
"Could use an update"
Reviewed on Jul 12, 2026
Cambria Hotel Portland Downtown-Old Port
25 HANCOCK STREET Portland ME
Fully refundable
The price is CA $452 per night from Jul 26 to Jul 27
CA $452
CA $539 total
Jul 26 - Jul 27
includes taxes & fees
9.4/10 Exceptional! (1,264 reviews)
"The room was perfect and spacious; the only downside was the view."
Reviewed on Jul 12, 2026
Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $559 per night from Jul 19 to Jul 20
CA $559
CA $673 total
Jul 19 - Jul 20
includes taxes & fees
9.4/10 Exceptional! (1,783 reviews)
"Our stay was great - the location of this hotel is perfect, the staff was friendly and our room was really nice. Every morning, there was a fully stocked pantry with snacks and drinks for guests on each floor. We had a great stay and would recommend this place highly!"
Reviewed on Jul 12, 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.
Frequently asked questions
Stay near popular Cumberland County attractions
What to do in Cumberland County
Sunset Windjammer Cruise Along the Coast of Portland Maine
CA $109
per adult
88% of travellers recommend
Portland Smartphone Audio Tour: Self-Guided Drive
CA $24
per traveller
100% of travellers recommend
Portland, Maine: Hidden Histories Guided Walking Tour
CA $77
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
