Cumberland County Holidays

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Top destinations in Cumberland County

A lighthouse, a white house with a red roof, and rocky coastline at sunset.
FlightsFlightsHotelsHotels

Portland

Portland

Our pick of the best Cumberland County Hotel Deals

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 NZ$613 per night from 5 July to 6 July
NZ$613
5 July - 6 July
includes taxes & fees
9.4/10 Exceptional! (1,773 reviews)
"Iron broken. Construction outside."

Reviewed on 26 June 2026

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 NZ$267 per night from 29 June to 30 June
NZ$267
29 June - 30 June
includes taxes & fees
7.8/10 Good! (1,007 reviews)
"Smelliest Hotel I have ever stepped foot in. Even motels in the middle of nowhere smelled better. It smelled like a wet dog has barfed and ate thay barf then barfed again and rolled in it then rolled all over the hotel. The staff is great but that smell is horrific it wasn’t just the hallways it ..."

Reviewed on 25 June 2026

Ramada Plaza by Wyndham Portland
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET Portland ME
Fully refundable
The price is NZ$539 per night from 5 July to 6 July
NZ$539
5 July - 6 July
includes taxes & fees
9.4/10 Exceptional! (1,248 reviews)
"The air conditioning doesn’t stay on. The thermostat goes down to 64 but the temperature wouldn’t go below 69 which made it pretty warm to try and sleep."

Reviewed on 26 June 2026

Cambria Hotel Portland Downtown-Old Port
See all 2,295 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

9.2/5 (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

Discover Portland City and Lighthouse Tour

Discover Portland City and Lighthouse Tour

NZ$97
per adult
94% of travellers recommend
Discover Portland City and Lighthouse Tour
Portland Maine Self-Guided Driving & Walking Audio Tour Bundle

Portland Maine Self-Guided Driving & Walking Audio Tour Bundle

NZ$43
per adult
90% of travellers recommend
Portland Maine Self-Guided Driving & Walking Audio Tour Bundle
Portland Self-Guided Driving Audio Tour

Portland Smartphone Audio Tour: Self-Guided Drive

NZ$29
per traveller
100% of travellers recommend
Portland Smartphone Audio Tour: Self-Guided Drive
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.