Cumberland County Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Rob Gosse

Top destinations in Cumberland County

Portland Head Light showing a lighthouse, general coastal views and rugged coastline
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Portland

Portland

Top hotels in Cumberland County

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 2.897.979 ₫ per night from 18 Dec to 19 Dec
2.897.979 ₫
4.209.936 ₫ total
18 Dec - 19 Dec
includes taxes & fees
9.2/10 Wonderful! (1,713 reviews)
Location

Reviewed on 15 Dec 2025

Portland Harbor Hotel
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
9.4/10 Exceptional! (1,546 reviews)
Everything

Reviewed on 8 Dec 2025

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Portland Regency Hotel & Spa
Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront

4 out of 5
9 Center Street Portland ME
Fully refundableReserve now, pay when you stay
The price is 3.214.189 ₫ per night from 22 Dec to 23 Dec
3.214.189 ₫
3.556.179 ₫ total
22 Dec - 23 Dec
includes taxes & fees
9.4/10 Exceptional! (1,004 reviews)
Great location. Clean rooms. Good restaurants with Ken walking distance.

Reviewed on 11 Dec 2025

Canopy by Hilton Portland Waterfront
See all 2,155 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 1null000null000 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.