Cumberland County Holidays

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Top destinations in Cumberland County

A lighthouse and houses on a rocky coastline with the ocean in the background.
FlightsFlightsHotelsHotels

Portland

Portland

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 refundable
The price is NZ$191 per night from 24 Nov to 25 Nov
NZ$191
24 Nov - 25 Nov
includes taxes & fees
9/10 Wonderful! (1,011 reviews)
"Perfectly situated in downtown Portland, near bars, restaurants, shops and galleries. Hotel is impeccably maintained and staff couldn’t be friendlier. Will be back!"

Reviewed on 8 Nov 2026

The Westin Portland Harborview
Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
Fully refundable
The price is NZ$159 per night from 24 Nov to 25 Nov
NZ$159
24 Nov - 25 Nov
includes taxes & fees
8.2/10 Very good! (1,869 reviews)
"Hotel is definitely dated. Our comforter was bloodstained."

Reviewed on 9 Nov 2026

Clarion Hotel Portland Airport ME
Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

3 out of 5
81 Riverside St Portland ME
Fully refundableReserve now, pay when you stay
The price is NZ$159 per night from 19 Nov to 20 Nov
NZ$159
19 Nov - 20 Nov
includes taxes & fees
8.2/10 Very good! (1,019 reviews)
"Older property, room was very clean, gym was clean and all equipment functional. Conveniently located for shopping and dining. Easy access to highway."

Reviewed on 10 Nov 2026

Fireside Inn & Suites Portland
See all 2,144 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.

Frequently asked questions

How much does a Cumberland County holiday package cost?
Custom build your Cumberland County holiday package from an affordable . 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

A building with 'L.L. Bean Inc.' signage, a large boot sculpture, and outdoor seating.

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.
See properties

What to do in Cumberland County

Portland Self-Guided Driving Audio Tour

Portland Smartphone Audio Tour: Self-Guided Drive

NZ$30
per traveller
100% of travellers recommend
Portland Smartphone Audio Tour: Self-Guided Drive
Portland Maine Self-Guided Driving & Walking Audio Tour Bundle

Portland Maine Self-Guided Driving & Walking Audio Tour Bundle

NZ$44
per adult
90% of travellers recommend
Portland Maine Self-Guided Driving & Walking Audio Tour Bundle
Ultimate Portland Self-Guided Driving GPS Audio Tour

Ultimate Portland Self-Guided Driving GPS Audio Tour

NZ$30
per traveller
100% of travellers recommend
Ultimate Portland Self-Guided Driving GPS Audio Tour
See all activities in Cumberland County
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.