Cumberland County Holidays from AU$3,658

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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.
Beacon Hill Hotel

Beacon Hill Hotel

4 out of 5
Beacon Hill
per person
15 Sept - 22 Sept
found 15 hours ago
Return flight included
Brisbane (BNE) to Boston (BOS)
8.8/10 Excellent! (235 reviews)
We enjoyed having the bistro on site.

Reviewed on 17 Jul. 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
15 Sept - 22 Sept
found 15 hours ago
Return flight included
Brisbane (BNE) to Boston (BOS)
9.6/10 Exceptional! (135 reviews)
Awesome hotel. Staff is great. Best hotel in Boston! And I've stayed at alot of em.

Reviewed on 11 Aug. 2025

Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Save 100% on your flight
per person
15 Sept - 22 Sept
found 15 hours ago
Return flight included
Brisbane (BNE) to Boston (BOS)
8.8/10 Excellent! (1,021 reviews)
The bed was comfortable

Reviewed on 10 Aug. 2025

YOTEL Boston

YOTEL Boston

4 out of 5
Seaport District
per person
15 Sept - 22 Sept
found 15 hours ago
Return flight included
Brisbane (BNE) to Boston (BOS)
8.6/10 Excellent! (2,132 reviews)
The room was nice and cozy, slept like a log all 3 nights.

Reviewed on 12 Aug. 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
15 Sept - 22 Sept
found 15 hours ago
Return flight included
Brisbane (BNE) to Boston (BOS)
9.8/10 Exceptional! (1,014 reviews)
The Boston Harbor Hotel continues to be my absolute favorite place to stay in Boston, and my recent visit reminded me exactly why. From the moment I walked through the doors, I was greeted by the same welcoming and professional staff that makes this property truly special. The team went above and beyond by upgrading me to a suite, which was an unexpected and much-appreciated gesture that really enhanced my stay. The suite itself was beautifully appointed and comfortable, providing the perfect retreat after busy days exploring the city. What really sets this hotel apart is its unbeatable location. You simply cannot find a better spot in Boston - it's perfectly positioned for both business and leisure activities, with easy access to everything the city has to offer while maintaining that sense of waterfront tranquility. Every stay here has been delightful, and the consistency in service quality is remarkable. The Boston Harbor Hotel has earned my loyalty through their attention to detail and genuine hospitality. I'm already looking forward to my next visit!

Reviewed on 11 Aug. 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

Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
155 Riverside St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is AU$225 per night from 1 Sept to 2 Sept
AU$225
1 Sept - 2 Sept
includes taxes & fees
7.6/10 Good! (1,042 reviews)
"."

Reviewed on 9 Aug. 2025

Ramada Plaza by Wyndham Portland
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$350 per night from 1 Sept to 2 Sept
AU$350
1 Sept - 2 Sept
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"Nice property could add some vending machines by ice machines for soft drinks and snacks."

Reviewed on 24 Jul. 2025

The Westin Portland Harborview
Clarion Hotel Portland

Clarion Hotel Portland

2.5 out of 5
1230 Congress St, Portland, ME
The price is AU$258 per night from 18 Aug to 19 Aug
AU$258
18 Aug - 19 Aug
includes taxes & fees
7.8/10 Good! (1,006 reviews)
"Comfortable bed, easy check in and check out"

Reviewed on 9 Aug. 2025

Clarion Hotel Portland
See all 2,202 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Cumberland County holiday package cost?
Custom build your Cumberland County holiday package from an affordable AU$3,658. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.