Cumberland County Holidays from AU$1,015

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Your Cumberland County Holiday

Head off on your next adventure with a Cumberland County holiday package, and leave knowing all the details are taken care of. And with the ability to tailor your escape, you know it'll be one to remember! Why not plan your trip to Cumberland County around some of its most well-known cities? Portland, South Portland and Freeport are terrific places to begin. Expedia has flights, hotels and all your other travel needs to help you curate your dream Cumberland County holiday today.

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.
The Westin Boston Seaport District

The Westin Boston Seaport District

4 out of 5
Seaport District
per person
22 Apr - 24 Apr
found 22 hours ago
Return direct flight included
Toronto (YYZ) to Boston (BOS)
9/10 Wonderful! (1,733 reviews)
Amazing, friendly staff, seamless experience

Reviewed on 18 Feb. 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
22 Apr - 24 Apr
found 22 hours ago
Return direct flight included
Toronto (YYZ) to Boston (BOS)
9.6/10 Exceptional! (1,006 reviews)
Very kid friendly for an upscale hotel.

Reviewed on 18 Feb. 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
per person
22 Apr - 24 Apr
found 22 hours ago
Return direct flight included
Toronto (YYZ) to Boston (BOS)
9.6/10 Exceptional! (1,002 reviews)
The room I viewed when I booked, looked nothing like the room I received. The window was beautiful but only had a view of the next building (could not see a thing else). Like because of the shape you couldn’t even see the motion of downtown Boston. We had to request new face towels as soon as we got to the room, the ones already in the bathroom looked a little dirty. Other than that the hotel is beautiful. Staff are very welcoming! Valet was amazing even in the cold!

Reviewed on 21 Feb. 2025

Battery Wharf Hotel, Boston Waterfront

Battery Wharf Hotel, Boston Waterfront

4.5 out of 5
North End
per person
22 Apr - 24 Apr
found 22 hours ago
Return direct flight included
Toronto (YYZ) to Boston (BOS)
8.6/10 Excellent! (1,537 reviews)
The shower was not working appropriately. It was a selling point on this room and was a let down

Reviewed on 19 Feb. 2025

Courtyard by Marriott Boston Downtown/North Station

Courtyard by Marriott Boston Downtown/North Station

3 out of 5
West End
per person
22 Apr - 24 Apr
found 22 hours ago
Return direct flight included
Toronto (YYZ) to Boston (BOS)
9.4/10 Exceptional! (1,008 reviews)
Great location, beautiful clean rooms

Reviewed on 21 Feb. 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

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$156 per night from 9 Mar to 10 Mar
AU$156
includes taxes & fees
9 Mar - 10 Mar
8.8/10 Excellent! (1,002 reviews)
10/10 wouldn’t stay anywhere else in portland
"I can’t say enough good about the staff or the property. The valet crew was top notch and friendly, offering tips, directions and even shuttle rides across town as the weather was poor and since they had time they said they didn’t see a need for me to take a lyft. The front desk hooked us up with ..."

Reviewed on 17 Feb. 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$272 per night from 16 Mar to 17 Mar
AU$272
includes taxes & fees
16 Mar - 17 Mar
9/10 Wonderful! (1,467 reviews)
"Very clean and comfortable. Nice fitness center. Snacks, tea, coffee, water 24/7. Friendly staff!"

Reviewed on 19 Feb. 2025

Portland Harbor Hotel
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$162 per night from 24 Feb to 25 Feb
AU$162
includes taxes & fees
24 Feb - 25 Feb
7.6/10 Good! (1,023 reviews)
Good but needs attention in the bathroom.
"It was good, loved the hot tub availability. Would be nice if it was open later than 1000. Room was comfortable and clean. The hot water availability is not so great, At the end of my shower, the water was no longer hot. I do not take a long shower-5 min max, there was no hot water when my husband ..."

Reviewed on 16 Feb. 2025

Ramada Plaza by Wyndham Portland
See all 2,037 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$1,015. 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.