Cumberland County Holidays from AU$3,837

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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 Head Light featuring rocky coastline, general coastal views and a lighthouse
FlightsFlightsHotelsHotels

Portland

Portland

The Latest Cumberland County Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Encore Boston Harbor

Encore Boston Harbor

5 out of 5
Price was AU$4,612, price is now AU$3,837 per person
AU$3,837
per person
17 Dec - 23 Dec
found 23 hours ago
Return flight included
Brisbane (BNE) to Boston (BOS)
19.2/10 Exceptional! (3,373 reviews)
I had an amazing stay at Encore Boston, and several things truly stood out. First, the cleanliness of the room was next-level; spotless, modern, and beautifully designed. You can tell the housekeeping team takes real pride in their work. The staff were equally impressive. Every interaction felt warm, professional, and genuine. From check-in to check-out, everyone made me feel welcomed and taken care of. The amenities are where Encore really separates itself; the entire property feels luxurious, from the casino floor to the restaurants, shops, and common areas. Everything is thoughtfully maintained, well-organized, and designed to elevate your experience. Overall, Encore Boston delivered exactly what a 5-star resort should provide: impeccable cleanliness, outstanding staff, and world-class amenities. I’ll definitely be returning and recommending it to others.

Reviewed on 14 Nov 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was AU$5,060, price is now AU$4,047 per person
AU$4,047
per person
17 Dec - 23 Dec
found 23 hours ago
Return flight included
Brisbane (BNE) to Boston (BOS)
19.6/10 Exceptional! (1,008 reviews)
Rooms were spotless, service was outstanding

Reviewed on 13 Nov 2025

XV Beacon

XV Beacon

5 out of 5
Beacon Hill
Price was AU$5,594, price is now AU$4,498 per person
AU$4,498
per person
17 Dec - 23 Dec
found 23 hours ago
Return flight included
Brisbane (BNE) to Boston (BOS)
18.8/10 Exceptional! (383 reviews)
I had a wonderful experience at the XV Beacon Hotel. The room and bathroom was modern and updated. I also thought the gym was clean.

Reviewed on 10 Nov 2025

The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Price was AU$4,765, price is now AU$3,948 per person
AU$3,948
per person
17 Dec - 23 Dec
found 23 hours ago
Return flight included
Brisbane (BNE) to Boston (BOS)
18.8/10 Exceptional! (532 reviews)
This hotel has it all, best in class care and service.

Reviewed on 24 Oct 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was AU$4,952, price is now AU$4,230 per person
AU$4,230
per person
17 Dec - 23 Dec
found 23 hours ago
Return flight included
Brisbane (BNE) to Boston (BOS)
19.2/10 Exceptional! (1,000 reviews)
I stayed more than once in the Langham , the whole staff is awesome especially the reception guys and ladies, Ella and Geremy made the effort for a pleasant stay , Wanda from the housekeeping was so caring and helpful , the whole team made me always feel at home . I surely will be there whenever I ‘ll visit Boston .

Reviewed on 13 Nov 2025

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

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
Fully refundableReserve now, pay when you stay
The price is AU$138 per night from 17 Nov to 18 Nov
AU$138
17 Nov - 18 Nov
includes taxes & fees
7.8/10 Good! (1,231 reviews)
Room was clean.everything worked . Staff was helpful and friendly.

Reviewed on 11 Nov 2025

Clarion Hotel Portland Airport ME
The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is AU$151 per night from 30 Nov to 1 Dec
AU$151
30 Nov - 1 Dec
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
Clean room and location

Reviewed on 3 Nov 2025

The Westin Portland Harborview
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street, Portland, ME
Fully refundableReserve now, pay when you stay
The price is AU$258 per night from 23 Nov to 24 Nov
AU$258
23 Nov - 24 Nov
includes taxes & fees
9.2/10 Wonderful! (1,666 reviews)
Great rooms, walk-able to everything, super clean, great staff, the restaurant is delicious and the bar has good drinks, very accommodating and lots of extras! The 4 stars are for parking... we would like to keep our car inside the garage, to do so it must be valet, that is not an option for some ...

Reviewed on 12 Nov 2025

Portland Harbor Hotel
See all 2,125 properties in Cumberland County
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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Frequently asked questions

How much does a Cumberland County holiday package cost?
Custom build your Cumberland County holiday package from an affordable AU$3,837. 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.

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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.