Cumberland County Vacations & Trips from $220
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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
Brunswick
The Latest Cumberland County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Cambria Hotel & Suites Plymouth
Save 100% on your flight
Price was $576, price is now $364 per person
$364
per person
Nov 13 - Nov 18
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.2/10 Wonderful! (61 reviews)
The hotel was superb and very clean the rooms were spacious and well maintained. It is one of the nicest hotels I’ve stayed in the staff were very friendly and helpful.
Reviewed on Sep 29, 2025
D. Hotel Suites & Spa
Save 100% on your flight
Price was $783, price is now $505 per person
$505
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
9.4/10 Exceptional! (2,230 reviews)
Hotel is nice and rooms are nice. They could use some updating of the furniture in the room I stayed at but overall a nice place with a nice breakfast included
Reviewed on Sep 30, 2025
Pennyweight Hotel Boston, Curio Collection by Hilton
West End
Save 100% on your flight
Price was $966, price is now $624 per person
$624
per person
Dec 10 - Dec 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.2/10 Very Good! (1,141 reviews)
Spur-of-the-moment decision to stay at Pennyweight based on proximity to Boston's North Station. Compared to three other nearby options, price was right. Two nights. If you're looking for a place to sleep and shower and want location near North Station, TD Garden and North End, you overlook the very small room (king), limited in-house dining, limited lounge seating, and neutral lobby ambience. But hey, plenty of eating and socializing options nearby. Friendly front desk and overall clean environment.
Reviewed on Sep 28, 2025
Cumberland County Hotel Deals
Clarion Hotel Portland
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
$144 nightly
The price is $159 total per night from Oct 8 to Oct 9
$159 total
Oct 8 - Oct 9
Total with taxes and fees
7.8/10 Good! (1,091 reviews)
"Not bad at all"
Reviewed on Sep 22, 2025
Fireside Inn & Suites Portland
81 Riverside St, Portland, ME
Fully refundableReserve now, pay when you stay
$114 nightly
The price is $126 total per night from Oct 26 to Oct 27
$126 total
Oct 26 - Oct 27
Total with taxes and fees
7.8/10 Good! (1,037 reviews)
"Front desk staff was helpful with dining suggestions."
Reviewed on Sep 25, 2025
Canopy by Hilton Portland Waterfront
9 Center Street, Portland, ME
Fully refundableReserve now, pay when you stay
$221 nightly
The price is $245 total per night from Oct 27 to Oct 28
$245 total
Oct 27 - Oct 28
Total with taxes and fees
9.4/10 Exceptional! (1,021 reviews)
"Beautiful and convenient property. Excellent staff. Rooftop bar has gorgeous views- a must!!!"
Reviewed on Sep 28, 2025
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.