
Cumberland County Vacations & Trips from $390
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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

Raymond
The Latest Cumberland County Vacation Packages
Price found within the past 48 hours. Click for updated prices.

Boston Lodge and Suites
Dorchester
Price was $956, price is now $390 per person
$390
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.4/10 Very Good! (194 reviews)
The accommodation was great and spacious enough for a large group. There were five of us, and it was perfect for our needs. The apartment was clean, and everything we needed was provided, including towels, soap, dishwasher detergent, and more.
We turned on the oven to make dinner, but we were unable to turn it off because the buttons weren’t working. We called for assistance and received a response very quickly, which made us feel supported and taken care of.
Overall, we had a great stay! The apartment was lovely, and the location was excellent, especially for getting to Boston by public transportation.
Reviewed on Oct 17, 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

The Westin Portland Harborview
157 High St Portland ME
Fully refundable
$91 nightly
The price is $101 total per night from Dec 6 to Dec 7
$101 total
Dec 6 - Dec 7
Total with taxes and fees
9/10 Wonderful! (1,006 reviews)
"Good but not as good as a typical Westin at all. Needs to be updated"
Reviewed on Nov 14, 2026

Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundable
$76 nightly
The price is $84 total per night from Nov 22 to Nov 23
$84 total
Nov 22 - Nov 23
Total with taxes and fees
8.2/10 Very Good! (1,874 reviews)
"Super easy check in and check out. They had Good coffee and microwave in room, which is always appreciated"
Reviewed on Nov 14, 2026

Fireside Inn & Suites Portland
81 Riverside St Portland ME
Fully refundableReserve now, pay when you stay
$77 nightly
The price is $85 total per night from Nov 22 to Nov 23
$85 total
Nov 22 - Nov 23
Total with taxes and 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.
Stay near popular Cumberland County attractions
What to do in Cumberland County

Phantoms, Penance, and Poltergeists: Portland, ME Ghost Tour
$32
per adult

A Walk Through Time Tour in Portland
$49
per adult
98% of travellers recommend

Portland Smartphone Audio Tour: Self-Guided Drive
$17
per traveler
100% of travellers recommend
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