Cumberland County Holidays from AU$3,326
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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
Portland
The Latest Cumberland County Holiday Deals
Price found within the past 48 hours. Click for updated prices.
The Revolution Hotel
South End
AU$3,326
per person
17 Dec - 26 Dec
found 1 day ago
Return flight included
Brisbane (BNE) to Boston (BOS)
9/10 Wonderful! (2,940 reviews)
Well put together. We had our own bathroom but the shared ones were immaculate. Almost nicer. Well set up. Small room but it’s historic Boston. Well put together, arranged well. Many shelves & places to put things. Great coffee downstairs. Didn’t have time to eat but Mexican place looked bomb. Make a great margarita. Cool vibe. Safe, clean, well lit. Chill. Residential street on side. Quiet & calm. Easy pick up & drop off for uber. Windows open easily. Best pillows ever. 93/100 sleep score. My Apple Watch was impressed with this bed.
Reviewed on 1 Oct 2026
Eurostars The Boxer
West End
AU$3,408
per person
17 Dec - 26 Dec
found 1 day ago
Return flight included
Brisbane (BNE) to Boston (BOS)
8.8/10 Excellent! (1,597 reviews)
The hotel overall was ok. I would expect more from a 4 star hotel. Our room never seemed to be super clean. The carpets didn’t appear to get vacuumed and trash was left on the nightstand. We also got plenty of towels the first couple of nights but nights 3 and 4, they were scarce and I had to ask the front desk for some. That being said, the location was really good and concierge was nice and attentive but would probably look to stay somewhere else nearby next time.
Reviewed on 30 Sept 2026
Bricco Suites
North End
AU$3,627
per person
17 Dec - 26 Dec
found 1 day ago
Return flight included
Brisbane (BNE) to Boston (BOS)
9/10 Wonderful! (999 reviews)
A unique setting compared to other hotels. Older part of Boston, interesting neighborhood and building.
Staff very friendly and helpful.
Reviewed on 30 Sept 2026
Cumberland County Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Portland Intl. Jetport Airport (PWM) |
Top Sights | Higgins Beach, Sebago Lake and Sebago Lake State Park |
Our pick of the best Cumberland County Hotel Deals
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundableReserve now, pay when you stay
AU$113
1 Nov - 2 Nov
includes taxes & fees
Inn at St John Portland In-Town
939 Congress St Portland ME
AU$140
1 Nov - 2 Nov
includes taxes & fees
8.6/10 Excellent! (1,150 reviews)
"We had a lovely stay at The Inn on St. John! It’s a very unique hotel with a lot of character, both inside and out. Our room was comfortably spacious and featured a fantastic shower—plus, having a jet bath was a wonderful bonus! The complimentary morning breakfast was a great touch to start the day. ..."
Reviewed on 30 Sept 2026
Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
AU$325
1 Nov - 2 Nov
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 holiday package cost?
Custom build your Cumberland County holiday package from an affordable AU$3,326. Choose from any combination of flights, hotels and rental cars to put together the escape you've been dreaming about. Don't forget to add on a few experiences or activities!
How do I get a cheap travel package to Cumberland County?
Bundling your hotel and flight with Expedia won't just save precious time — it'll save you dollars too. A Cumberland County holiday package makes it a breeze to create the perfect trip. With more than 550 airlines across the world to select from, finding flights that fit your schedule won't be a hassle. Not only that, we've got over 1 000 000 properties globally to take your pick of. Now that's what you call choice. Whatever your budget, Expedia puts more of the world within your reach.
Where should I stay in Cumberland County?
If you've always wanted to explore Portland Head Light and University of Southern Maine, the city of Portland is calling your name.
What are the top hotels in Cumberland County?
The Westin Portland Harborview and La Quinta Inn & Suites by Wyndham Portland know how to make their guests feel at home in Portland. If your travel plans also include Bridgton, look up Portland Harbour Hotel and Casco Bay Hotel, Ascend Hotel Collection. Both are popular with travellers.
How far in advance should I book my Cumberland County holiday?
Travellers are usually able to compare international airfares on Expedia up to 12 months prior to departure. Booking late? With a little bit of luck, it's still possible to purchase an affordable ticket just weeks before your flight.
What does an Expedia Cumberland County travel package include?
Hotels, car rentals and flights — we bring you the best deals. All you have to do is figure out your preferred combination. After you've made your booking, you can add on the fun stuff like tours and experiences. Our travel packages make it easy to put together an unforgettable Cumberland County escape.
What should I know before booking a Cumberland County travel package?
An Expedia travel package can be customized for your budget and is a terrific way to make your hard-earned dollars stretch further. How little or much you include is totally up to you. Rental cars, hotels and flights — come up with a combination that suits your style.
Can I choose my airline with a Cumberland County Expedia holiday package?
Expedia offers access to more than 550 airline partners globally, so you certainly can. Just choose the airline you want and craft the perfect Cumberland County escape.
If I'm not able to travel, can I cancel my Cumberland County holiday package?
Yes, it's possible to cancel your Cumberland County booking if your travel plans have been upended. Whether you'll incur a fee or not depends on your airline, hotel or car rental company. It may be possible to change or cancel free of charge if you booked in the last 24 hours. Visit our Customer Service Portal to learn more.
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.
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.
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.
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.
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 great live music and entertainment choices.
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.
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.
What to do in Cumberland County
The Real Portland Tour: City and 3 Lighthouses Historical Tour with a Real Local
AU$104
per adult
100% of travellers recommend
Portland: Casco Bay Morning Lighthouse Cruise
AU$83
per adult
80% of travellers recommend
Sunset Windjammer Cruise Along the Coast of Portland Maine
AU$108
per adult
90% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
