Cumberland County Vacations & Trips from $511
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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.
The Wylie Inn and Conference Center at Endicott College
Price was $693, price is now $511 per person
$511
per person
May 24 - May 28
found 3 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.2/10 Wonderful! (1,174 reviews)
Great location near the beach and close to Boston Logan Airport.
Reviewed on Mar 24, 2026
The Langham, Boston
Downtown Boston
Save 100% on your flight
Price was $2,614, price is now $1,570 per person
$1,570
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
9.6/10 Exceptional! (1,004 reviews)
Room was spacious, clean & well set up. Nice that they use Dyptique hand soap shampoo & shower gel. That is a 5 star touch.
Bed was nice and very quiet location.
Reviewed on Mar 22, 2026
Boston Harbor Hotel
North End
Save 100% on your flight
Price was $2,387, price is now $1,606 per person
$1,606
per person
Jun 4 - Jun 7
found 3 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Everything was great, however the pool itself was not heated, it was cold and no one really stayed in it for that reason. Thankfully there was a hot tub.
Reviewed on Mar 23, 2026
The Colonnade Hotel Back Bay
Back Bay
Save 100% on your flight
Price was $1,429, price is now $1,038 per person
$1,038
per person
Jun 2 - Jun 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.2/10 Wonderful! (2,282 reviews)
It's a beautiful hotel with very nice and cozy rooms. Staff friendly.
Reviewed on Mar 26, 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 refundableReserve now, pay when you stay
$106 nightly
The price is $117 total per night from Apr 13 to Apr 14
$117 total
Apr 13 - Apr 14
Total with taxes and fees
8.8/10 Excellent! (1,002 reviews)
I frequently stay at this property. It is a very clean property with kind and helpful staff and an excellent restaurant and spa. I was locked out of the next door parking garage and Dan (door man?) helped me get my car out. He ran out there in the freezing cold, called the garage mgmt and got me ...
Reviewed on Mar 26, 2026
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundable
$77 nightly
The price is $85 total per night from Apr 13 to Apr 14
$85 total
Apr 13 - Apr 14
Total with taxes and fees
8/10 Very Good! (1,403 reviews)
Great rooms and nice staff
Reviewed on Mar 26, 2026
Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
$161 nightly
The price is $178 total per night from Apr 5 to Apr 6
$178 total
Apr 5 - Apr 6
Total with taxes and fees
9.2/10 Wonderful! (1,761 reviews)
We paid a little extra for a room with a Courtyard view. What we got was a 2nd floor room as far as possible from the elevator and when I pulled back the curtains I was looking at a giant kitchen exhaust fan that gave us a constant deep buzz in the room. The hotel did not seem busy and this room ...
Reviewed on Mar 27, 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.
