Cumberland County Holidays

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    Save up to S$134 when you book a flight and hotel together*
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Top destinations in Cumberland County

Portland Head Light which includes general coastal views, a sunset and rocky coastline
FlightsFlightsHotelsHotels

Portland

Portland

Top hotels in Cumberland County

Hyatt Place Portland Downtown - Old Port Square
Hyatt Place Portland Downtown - Old Port Square
3 out of 5
433 Fore St, Portland, ME
The price is S$380 per night from 2 Jul to 3 Jul
S$380
2 Jul - 3 Jul
includes taxes & fees
8.8/10 Excellent! (1,145 reviews)
"Loved it's proximity to everything in Old Port!"

Reviewed on 28 Jun, 2025

Hyatt Place Portland Downtown - Old Port Square
Clarion Hotel Portland
Clarion Hotel Portland
2.5 out of 5
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is S$214 per night from 6 Jul to 7 Jul
S$214
6 Jul - 7 Jul
includes taxes & fees
7.8/10 Good! (1,009 reviews)
"Convenient location"

Reviewed on 30 Jun, 2025

Clarion Hotel Portland
Portland Regency Hotel & Spa
Portland Regency Hotel & Spa
3.5 out of 5
20 Milk Street, Portland, ME
9.2/10 Wonderful! (1,331 reviews)
Hotel stay
"From the minute we pullednin the staff were kind and very helpful. We loved the garden cafe accros from the hotel, its part of it. Great food and drinks. Staff again were so friendly. Above and beyound staff. Were kocals and had a night away, and it was so worth it."

Reviewed on 28 Jun, 2025

Get rates
Portland Regency Hotel & Spa
See all 2,244 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.