Cumberland County Holidays from AU$3,321
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to AU$2,500 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Arcadian Hotel
Coolidge Corner
AU$3,321
per person
5 Oct - 13 Oct
found 18 hours ago
Return direct flight included
Sydney (SYD) to Boston (BOS)
8.2/10 Very good! (4,382 reviews)
The property was clean and staff was friendly. Location is in a safe and vibrant part of town. Very walkable area. but the breakfast offerings were inedible for anyone with a gluten allergy. Literally every choice was gluten with absolutely no fresh fruit offered. It was all waffles, toast, muffins, cereal.
Reviewed on 15 Aug 2026
Hotel AKA Boston Common
Downtown Boston
AU$4,461
per person
5 Oct - 13 Oct
found 18 hours ago
Return direct flight included
Sydney (SYD) to Boston (BOS)
9/10 Wonderful! (1,732 reviews)
Great staff, Saheed was pleasant and courteous. Lovely room, clean and nice modern furniture. The staff in the restaurant are very attentive and friendly, the bartender Kathleen made excellent mixed drinks and was pleasant to talk to.
Reviewed on 14 Aug 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 refundable
AU$204
1 Sept - 2 Sept
includes taxes & fees
8/10 Very good! (1,616 reviews)
"The property was not well maintained. Curtains were torn in my room. Walls and vent were dirty, refrigerator was missing a foot so it fell forward when trying to open door.only one elevator working. Restaurant was not open as advertised, breakfast only. No shuttle service available when I arrived. ..."
Reviewed on 15 Aug 2026
Portland Regency Hotel & Spa
20 Milk Street Portland ME
AU$474
7 Sept - 8 Sept
includes taxes & fees
9.4/10 Exceptional! (1,734 reviews)
"The front desk was not very friendly. Our room felt wet when we walked in. Bathroom had dust falling from the drop ceiling. Cleaners were upon request only and when we did request it, they didn’t take any trash so when we came back the room smelled. There was no ventilation and it was in the corner ..."
Reviewed on 14 Aug 2026
Fireside Inn & Suites Portland
81 Riverside St Portland ME
Fully refundableReserve now, pay when you stay
AU$162
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 holiday package cost?
Custom build your Cumberland County holiday package from an affordable AU$3,321. 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.
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
AU$110
per adult
90% of travellers recommend
Portland Explorer: Boat Cruise with Oysters & Prosecco
AU$196
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
