Cumberland County Vacations & Trips from $630
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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.
By the Sea Guests Bed & Breakfast & Suites
Save 100% on your flight
Price was $994, price is now $630 per person
$630
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.4/10 Exceptional! (195 reviews)
The location couldn’t have been more perfect and despite it being a holiday weekend the parking lot/BNB never felt crowded. Everyone we encountered was lovely and helpful, and the room was a perfect place to take a midday nap or unwind after hours on the beach! We would definitely stay again.
Reviewed on Jul 6, 2026
Good Hotels Boston
South End
Save 100% on your flight
Price was $1,933, price is now $1,075 per person
$1,075
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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
Nantucket Inn
Save 100% on your flight
Price was $2,028, price is now $1,146 per person
$1,146
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.2/10 Wonderful! (722 reviews)
The staff and amenities at The Nantucket Inn were excellent. In particular, we give a 'shout out' to Balford, who went the extra mile (more than once!) to ensure that my physically challenged husband was accommodated in the best possible and most comfortable way during our transportation to/from town, and to Lisa at the front desk, who was responsive and speedy to our every request for information. Convenient access to the airport (walking-distance) was a bonus, as was the availability of delicious breakfast options (for a cost) and evening cocktails. The kiddoes enjoyed both pools. We would choose to stay here again.
Reviewed on Jul 11, 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
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundable
$135 nightly
The price is $150 total per night from Jul 19 to Jul 20
$150 total
Jul 19 - Jul 20
Total with taxes and fees
8.2/10 Very Good! (1,549 reviews)
"Wonderful stay. The pool and hot tub were a major plus guest services on point!! My airport transport was not honored when we left. That's okay. I found another way to make it back. Very comfortable beds. Super clean. Bathrooms were lovely with plenty of towels and amenities."
Reviewed on Jul 11, 2026
Cambria Hotel Portland Downtown-Old Port
25 HANCOCK STREET Portland ME
Fully refundable
$340 nightly
The price is $376 total per night from Jul 13 to Jul 14
$376 total
Jul 13 - Jul 14
Total with taxes and fees
9.4/10 Exceptional! (1,263 reviews)
"Clean room, great location."
Reviewed on Jul 12, 2026
Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
$433 nightly
The price is $480 total per night from Jul 26 to Jul 27
$480 total
Jul 26 - Jul 27
Total with taxes and fees
9.4/10 Exceptional! (1,781 reviews)
"Very helpful staff and had snacks, coffee and water available 24/7"
Reviewed on Jul 11, 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.
Stay near popular Cumberland County attractions
What to do in Cumberland County
Portland Explorer | Maine History, Culture, & 3 Lighthouses Tour
$79
per adult
100% of travellers recommend
Sunset Windjammer Cruise Along the Coast of Portland Maine
$77
per adult
88% 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.
