Cumberland County Holidays
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- Better togetherSave up to £750 when you book a flight and hotel together*
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- Rest easyPackages with flights are ATOL protected
Your Cumberland County Holiday
When adventure calls, answer it with a tailor-made holiday 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 holiday to the second you come back home, Expedia will take care of you every step of the way.
Top destinations in Cumberland County
Top Cumberland County Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites
Dorchester
£816
per person
5 Nov - 10 Nov
found 11 hours ago
Return direct flight included
Manchester (MAN) to Boston (BOS)
8.4/10 Very good! (190 reviews)
Parking was not easy. It was advertised as free parming and the explanation made it seem simple enough but finding free street parking in the area is not easy and you co stantly have to move your vehicles.
Reviewed on 19 May 2026
The Whitney Hotel
Beacon Hill
£2,781
per person
19 Oct - 30 Oct
found 1 day ago
Return direct flight included
Birmingham (BHX) to Boston (BOS)
9.6/10 Exceptional! (600 reviews)
The location is very convenient, staff was polite and friendly, room was very comfortable.
Reviewed on 8 Aug 2026
Cumberland County Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Portland Intl. Jetport Airport (PWM) |
Top Sights | Sebago Lake, Higgins Beach and Sebago Lake State Park |
Top hotels in Cumberland County
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundable
£107
1 Sept - 2 Sept
includes taxes & fees
Portland Regency Hotel & Spa
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
£250
30 Aug - 31 Aug
includes taxes & fees
9.4/10 Exceptional! (1,731 reviews)
"Staff outstanding. 2 queen beds turned out to be full size, so very tight sleeping."
Reviewed on 12 Aug 2026
Fireside Inn & Suites Portland
81 Riverside St Portland ME
£87
8 Sept - 9 Sept
includes taxes & 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.
Frequently asked questions
How much does a Cumberland County travel package cost?
Starting from only £816, a travel package is your portal to low-cost travel. Create your own Cumberland County adventure by choosing from our wide range of hotels, airfares and rental cars.
If I'm not able to travel, can I cancel my Cumberland County travel package?
If your travel plans in Cumberland County have been upended, it's comforting to know that it's possible to cancel your booking. If you made your booking within the last 24 hours, you may be able to receive a refund. If your booking was made more than 24 hours ago, your airline, hotel or car rental company may impose a fee. To find out more, check our Customer Service Portal.
How do I get a cheap travel package to Cumberland County?
Bundle your bookings with Expedia to save big on your next exciting adventure. With over 550 partner airlines and 1,000,000 hotel options worldwide, your Cumberland County holiday package can be tailored exactly to suit your budget. With all those extra dollars, why not throw in a few fun experiences and tours? It's an easy way to unlock even more savings. Your dream holiday in Cumberland County is closer than you thought!
Does Expedia offer Book Now, Pay Later Cumberland County holidays?
We sure do. Expedia has joined forces with online lender Klarna to help you conveniently pay for your trip in instalments. Simply choose the payment plan that suits you best during checkout and take the stress out of budgeting for your next trip. Remember to bundle your flights, car hire and accommodation with Expedia to get the biggest bang for your buck. Take a look at our flexible payment options below:
- Pay monthly holidays: If paying small amounts each month is what works best for you, Klarna can help. Paying in convenient monthly instalments will make that dream holiday possible.
- Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it possible to pay off your trip in multiple transactions.
- Low deposit holidays: Clicking the "book now" button is easier with this plan. Just put down a small deposit on your escape and then start packing your bags.
Where should I stay in Cumberland County?
You can't go wrong in Portland. Popular sights, such as Portland Head Light and University of Southern Maine, will keep you on the go in this exciting city.
What are the top hotels in Cumberland County?
When it comes to hotels in Portland, The Westin Portland Harborview and Portland Sheraton at Sable Oaks are two great options. If you're also visiting Bridgton, The Westin Portland Harborview and Portland Sheraton at Sable Oaks look forward to welcoming you.
How far in advance should I book my Cumberland County holiday?
While not all airlines release tickets early, you can normally compare international airfares on Expedia up to 12 months in advance. This is the time you'll bag some fantastic bargains. If you're booking last minute, you could still be in luck. Low prices occasionally become available only weeks prior to departure.
What does an Expedia Cumberland County travel package include?
Rental cars, flights and hotels — we've got them well covered. With Expedia, you can shape your Cumberland County package just the way you want. All you have to do is determine what you need. Once you've made your booking, you can add on extras like experiences and activities. The more you bundle, the bigger your savings!
What should I know before booking a Cumberland County travel package?
Whether it's adventure or relaxation you're seeking, a Cumberland County travel package lets you organise your escape your way. Plus, you'll score great discounts when you combine your accommodation with your rental car and flights. The more you bundle, the more you'll save!
Can I choose my airline with a Cumberland County Expedia travel package?
Yes, you're in charge. We have access to over 550 partner airlines around the world, so you can design your Cumberland County holiday according to your budget and needs.
Stay near popular Cumberland County attractions
LL Bean Flagship Store
9.2/10 (1,289 reviews)
During your visit to Freeport, you can enjoy retail therapy at LL Bean Flagship Store. Stroll along the area's waterfront or simply enjoy its seafood restaurants.
Portland Head Light
9.4/10 (928 reviews)
Look out across the Atlantic Ocean from Portland’s iconic white lighthouse, which has presided over the southern Maine coastline since the 18th century.
State Theatre
8.8/10 (392 reviews)
The beautiful mix of architectural styles, from Art Deco to Moorish, makes this newly renovated performing arts venue one of New England’s best.
Higgins Beach
8.8/10 (308 reviews)
At the mouth of the Spurwink River in Scarborough, take a stroll on the white sand or paddle a kayak over gentle waves.
Thompson's Point
8.8/10 (376 reviews)
Commune with nature and explore the great outdoors at Thompson's Point during your travels in Portland. Stroll along the waterfront or attend a sporting event in the area.
Maine Mall
8.4/10 (1,708 reviews)
You can browse for the perfect souvenirs at Maine Mall during your stay in South Portland. Experience the area's entertainment choices and great live music.
Cross Insurance Arena
8.6/10 (275 reviews)
Catch an event at Cross Insurance Arena during your trip to Portland. Stroll along the area's waterfront or experience its great live music.
What to do in Cumberland County
Sunset Windjammer Cruise Along the Coast of Portland Maine
£58
per adult
90% of travellers recommend
Portland Explorer: Boat Cruise with Oysters & Prosecco
£103
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
