Cumberland County Holidays from AU$1,490

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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.
Copley House

Copley House

3 out of 5
Back Bay
per person
13 Mar - 17 Mar
found 16 hours ago
Return direct flight included
London (LON) to Boston (BOS)
8.8/10 Excellent! (1,506 reviews)
Great stay! Great location! Great atmosphere!

Reviewed on 10 Dec. 2024

Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
per person
13 Mar - 17 Mar
found 16 hours ago
Return direct flight included
London (LON) to Boston (BOS)
8.6/10 Excellent! (1,002 reviews)
The Copley is old school Boston. The hotel has lots of character and is located in one of the nicest parts of the city Back Bay.

Reviewed on 22 Dec. 2024

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
13 Mar - 17 Mar
found 16 hours ago
Return direct flight included
London (LON) to Boston (BOS)
9.6/10 Exceptional! (81 reviews)
V nice room deco and designs. Attentive staff who are in close touch via text. Great experience all around.

Reviewed on 29 Nov. 2024

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
13 Mar - 17 Mar
found 16 hours ago
Return direct flight included
London (LON) to Boston (BOS)
9.4/10 Exceptional! (311 reviews)
It’s definitely a cut above standard hotels.

Reviewed on 15 Dec. 2024

XV Beacon

XV Beacon

5 out of 5
Beacon Hill
per person
13 Mar - 17 Mar
found 16 hours ago
Return direct flight included
London (LON) to Boston (BOS)
9.4/10 Exceptional! (358 reviews)
Staff was extremely helpful

Reviewed on 21 Dec. 2024

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$176 per night from 7 Jan to 8 Jan
AU$176
includes taxes & fees
7 Jan - 8 Jan 2025
8.6/10 Excellent! (1,002 reviews)
"I had an incredible stay! This was my first time at the Westin Harborview. Upon check-in I was awarded “Guest of the Day” status with a top floor upgrade. It was such a sweet surprise and a wonderful experience. The harbor view is quite lovely and the next morning I watched a couple of cargo ships ..."

Reviewed on 18 Dec. 2024

The Westin Portland Harborview
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$166 per night from 26 Dec to 27 Dec
AU$166
includes taxes & fees
26 Dec - 27 Dec
7.6/10 Good! (1,009 reviews)
"This was a great place to stay at. Very easy to locate and close enough to everything. The room was very clean and stocked perfectly. It was a breeze to check in and out. There are 2 hot tubs on site. Definately a great place to stay especially for the money."

Reviewed on 14 Dec. 2024

Ramada Plaza by Wyndham Portland
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 25 Dec to 26 Dec
AU$258
includes taxes & fees
25 Dec - 26 Dec
9/10 Wonderful! (1,426 reviews)
"Nice hotel in a great location!"

Reviewed on 22 Dec. 2024

Portland Harbor Hotel
See all 1,995 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$1,490. 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.