Cumberland County Vacations & Trips from $602
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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 destinations in Cumberland County
South Portland
The Latest Cumberland County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Fairmont Copley Plaza, Boston
Back Bay
Save 100% on your flight
Price was $902, price is now $602 per person
$602
per person
Jul 25 - Jul 28
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9/10 Wonderful! (1,240 reviews)
Staff were nice .
The room was not clean and the bathroom has no venting and you can’t open a window so it was not hygienic at all.
Things are old and not that greatly maintained in the rooms.
The lobby and the location are amazing
Reviewed on May 13, 2026
Saco Bay Hotel
Save 100% on your flight
Price was $1,294, price is now $882 per person
$882
per person
Jul 30 - Aug 4
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
7.6/10 Good! (1,051 reviews)
Breakfast was good, plenty of parking, and this place was extremely clean! You can literally smell the cleanliness when you walk down the hallways. Bed quality was great. I would definitely stay here again! Staff was extremely friendly as well.
Reviewed on May 14, 2026
Find the Best Cumberland County Vacation Packages
Cumberland County Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Portland Intl. Jetport Airport (PWM) |
Top Sights | Sebago Lake, Higgins Beach and East End Beach |
Cumberland County Hotel Deals
Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
$235 nightly
The price is $260 total per night from May 26 to May 27
$260 total
May 26 - May 27
Total with taxes and fees
9.4/10 Exceptional! (1,770 reviews)
This hotel was the perfect location for us near our destination downtime Portland and was beautiful. Staff was wonderful and the room was great. No complaints.
Reviewed on May 15, 2026
Portland Regency Hotel & Spa
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
$202 nightly
The price is $223 total per night from May 26 to May 27
$223 total
May 26 - May 27
Total with taxes and fees
9.4/10 Exceptional! (1,652 reviews)
A hotel has control over cleanliness, upkeep, and service. This hotel ranks very poorly in service. Not a single smile from any staff at check-in, check-out, or requests. They advertise pickup from the airport is available but after a call before flight, after landing, and then 3 more calls after ...
Reviewed on May 12, 2026
Cambria Hotel Portland Downtown-Old Port
25 HANCOCK STREET Portland ME
Fully refundable
$177 nightly
The price is $196 total per night from May 26 to May 27
$196 total
May 26 - May 27
Total with taxes and fees
9.4/10 Exceptional! (1,219 reviews)
Perfect location and unique hotel with secure off street parking
Reviewed on May 14, 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.
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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.
